The Most Charming Small Towns in Each U.S. State

While there’s so much to see in the United States—including its national parks and big cities—there’s plenty to be said for the country’s small towns. Come upon one (perhaps on a road trip) and you can catch a glimpse of American life that’s hidden from the well-trodden path, but just as appealing.

With so many memorable small towns in the United States, it’s hard to pick the best ones in each state. But we’re giving it a shot. Here are 51 of the country’s most charming small towns (which we’ve defined as places of about 25,000 people or fewer) all with their own unique reason to visit—whether it’s their singular streets or spectacular outdoor adventure opportunities.

Dinner at Lil's Deb's (left); a few people walking along Warren Street (right) — Heading to Hudson? Stop by Lil’s Deb’s and Warren Street.

New York: Hudson

Why we love it: It’s artistic and full of unexpected, delicious dishes.
Where to stay: Rivertown Lodge occupies a cinema-turned-motel and has wood-burning stoves as well as Aussie Papillionaire bikes to borrow.

A former whaling hub almost 120 miles upriver from New York City, Hudson has been steadily on the rise since 2010, when indie rocker Melissa Auf der Maur transformed a historic foundry into the arts venue Basilica Hudson. These days, downtown’s Warren Street is lined with some of the region’s best-preserved architecture—Greek revival, federal, second empire, colonial revival—and its storefronts are filled with art galleries and antique shops, plus delights like Culture Cream, an ice cream parlor where the ice creams and sorbets include ingredients like kefir and kombucha. In fact, the food scene here is so impressive that it often draws notoriously discriminating New Yorkers for weekend pilgrimages to spots like the queer-owned “tropical comfort food” spot Lil’ Deb’s Oasis and the quietly radical Cafe Mutton, which serves dishes like monkfish brandade, stuffed duck neck, and collard green and manchego pie. Joining their ranks in December was Mel the Bakery, a Manhattan import from James Beard semifinalist Nora Faye Allen, where she sells her cult-hit breads and pastries, including a Beetlejuice-inspired loaf made with purple sweet potatoes and black sesame stripes.

Person staring at a series of large paintings — The Massachusetts Museum of Contemporary Art is located in a coverted Arnold Print Works factory complex.

Massachusetts: North Adams

Why we love it: This art-filled corner of the state stays true to its industrial roots.
Where to stay: Stay at the Porches Inn at Mass MoCA, which occupies a series of Victorian row houses and includes a Finnish-style sauna and outdoor hot tub, or Tourists, a reimagined motor lodge with a cool cocktail and natural wine bar on site.

A former factory town in the Berkshires, North Adams churned out bricks, shoes, marble, and pig iron from the late 1700s. These days, the town’s output is decidedly more creative: One of the largest contemporary art museums in the country, Mass MoCA occupies a 16-acre complex of 19th-century mill buildings that now brim with exhibitions by the likes of Sol LeWitt and James Turrell. (You’re also less than a 15-minute drive from the Clark Art Institute and the Williams College Museum of Art.) Continuing the postindustrial theme is Greylock Works, a former cotton-spinning mill that now houses a locally sourced restaurant called the Break Room, Berkshire Cider Project, and a Distillery at Greylock Works, which makes gins with locally foraged botanicals like black birch and wild berries.

Red and white buildings on a riverfront with trees — New Hope was once home to Aaron Burr.

Pennsylvania: New Hope

Why we love it: It’s history-steeped with a flair for drama.
Where to stay: The 12-room, riverfront Ghost Light Inn sits next to the Playhouse and is named for the single bulb that tradition dictates must be left on inside an empty theater.

Every summer since 1939, theater lovers have flocked to this corner of Pennsylvania—a few miles upriver from where Washington crossed the Delaware—to catch a show at the Bucks County Playhouse. Housed in an 18th-century grist mill that was rescued from demolition, the theater has attracted performers like Grace Kelly, Liza Minelli, and Robert Redford. Everything here comes with a backstory, like the Oldestone Steakhouse, in a converted 1872 stone church with a 20-foot-by-40-foot mural of St. George slaying the dragon. Elsewhere around this walkable colonial town, you can taste cognac-barrel-aged ciders at Manoff Market Gardens and Cidery and blackberry wine at New Hope Winery, take a stroll through the Bowman’s Hill Wildflower Preserve, or hop aboard the New Hope Railroad, a historic locomotive that takes riders through the bucolic Bucks County countryside.

Empty yellow lounge chairs (L); an empty wooden boardwalk (R) — The Asbury Hotel and boardwalk are two of Asbury Park’s points of interest.

New Jersey: Asbury Park

Why we love it: This revived beach town boasts a slew of stylish new hotels.
Where to stay: The St. Laurent Social Club, established in 1886, reopened in 2022, complete with a saltwater pool that offers swim day passes.

This Victorian seaside resort declined in the late 20th century due to urban flight and race riots, but it’s been slowly and steadily recapturing its old magic. Its boardwalk is thrumming once again, complete with a pinball machine museum and a retro beach bar with a popular dog-friendly Yappy Hour. The Stone Pony, a divey music venue that launched the careers of Bruce Springsteen and Jon Bon Jovi, celebrated its 50th anniversary in 2023, and its outdoor summer stage now hosts the likes of Carly Rae Jepsen and the Pixies. Nearby you’ll find destination restaurants like Talula’s, where the sourdough pizzas come with innovative toppings like okra and squash blossoms, and Glide Surf Co., which sells custom surfboards and wet suits. While Asbury Park is only about a 70-minute drive from New York City, accommodations like the Asbury and the Asbury Ocean Club Hotel practically beg you to stay overnight.

Two small boats on water seen from forested shore in Burlingame State Park — While in Charlestown, be sure to check out Burlingame State Park.

Rhode Island: Charlestown

Why we love it: For its picturesque, coastal village charm
Where to stay: The General Stanton Inn has welcomed guests—including George Washington and Theodore Roosevelt—since 1740.

A member of the Mashpee Wampanoag Tribe, chef Sherry Pocknett became the first Indigenous woman to win a James Beard Award in 2023, and her Sly Fox Den Too restaurant has put Charlestown on the culinary map with dishes like smoked scallops and fry bread tacos. It was a welcome addition to a town best known for its golden-sand beaches, hiking and biking trails, and the Ninigret National Wildlife Refuge, a magnet for migratory birds. Perhaps the funkiest spot in town is the Fantastic Umbrella Factory, a historic farmstead that’s been transformed into a shopping complex with gardens, a bamboo forest, and a menagerie that includes chickens and emus. Particularly noteworthy is the complex’s Native American–owned Purple Shell boutique, which sells handcrafted wampum jewelry made from quahog clam shells.

Aerial view of buildings and small boats alongside an inlet — Lewes anchors the Cape Region alongside Rehoboth Beach.

Delaware: Lewes

Why we love it: The former fishing port wears its history proudly.
Where to stay: The Dogfish Inn is a sustainable design hotel owned by Dogfish Head brewery and has a gear shed stocked with beach chairs, Woolrich blankets, and binoculars.

Nicknamed “The First Town in the First State,” Lewes was founded by the Dutch in 1631. That heritage is celebrated at the Zwaanendael Museum, which occupies an elaborately gabled building inspired by the former city hall of Hoorn in the Netherlands. The c. 1765 Cannonball House, which houses the Lewes Maritime Museum, still bears the scars of a skirmish with the British in 1813 (there’s a cannonball in a wall), while the Ryves Holt House Museum counted the Revolutionary War hero Jacob Jones among its early occupants. For dinner, don’t miss the James Beard–nominated Heirloom, which occupies a red-shuttered Victorian house; it serves seasonal dishes like steak tartare with kumquat relish and juniper-brined venison loin.

Garden with trees and pink flowers — One of the best times to visit the Hollister House Garden is during the spring.

Connecticut: Washington

Why we love it: For its cozy vibes that serve as the inspiration for Stars Hollow in Gilmore Girls
Where to stay: The Mayflower Inn & Spa is a member of the Auberge Resorts Collection that started life in 1894 as a boys’ boarding school and is now home to the Garden Room restaurant, where dishes include fried quail and fluke with smoked onion broth.

The town of Washington consists of five rural villages scattered around forested Litchfield Hills, a favorite region for fall foliage drives. In the village of New Preston, the best seat is at Community Table, where Christian Hunter earned a 2023 James Beard Award nomination for best chef in the Northeast. While you’re here, stop into the Institute for American Indian Studies Museum & Research Center, which traces 10,000 years of Indigenous history and features a replicated Algonquian village, and the Hollister House Garden, inspired by classic English gardens. Outside of town, hikers shouldn’t miss the Hidden Valley Preserve, nearly 1,000 acres of dense forests and meadows with almost 20 miles of trails and points of interest that include a former 19th-century quartz mine and a timber suspension bridge dedicated to Henry David Thoreau.

Brick sidewalk beside a park, with red brick buildings in background — Easton is in Talbot County, Maryland.

Maryland: Easton

Why we love it: For the brick sidewalks and stately architecture fused with forward-looking energy
Where to stay: The Hummingbird Inn is a dog-friendly B&B that occupies an 1887 Queen Anne–style house with a wraparound porch and a yard filled with giant magnolias.

Easton looks like many of the historic hamlets on Maryland’s Eastern Shore. But there’s also a surprising level of sophistication here in this Quaker-founded town that was once populated by sea merchants and farmers. The Academy Art Museum, for instance, occupies an 1820 schoolhouse, but its curation is future facing, with exhibits dedicated to artists like Oglala Lakota tribe member Marty Two Bulls, Jr. Easton also enjoys an outsize food and bar scene, thanks to energy executive Paul Prager, who fell in love with the place while at the Naval Academy in Annapolis. His Bluepoint Hospitality has completely reshaped the town, with openings like Bas Rouge, a refined Viennese-inspired restaurant with tableside guéridon (trolley) service, and the Stewart, a tartan-bedecked lounge with rare single-malt scotches. Beyond the historic district, bird lovers flock to these parts for the Pickering Creek Audubon Center; you can engage with the area’s feathered residents—more than 250 species have been recorded here—on the park’s hiking trails or in a kayak or canoe during the summer months.

Small boats at a dock, with green trees in background — In a state filled with lovable small towns, we’re partial to this formerly blue-collar Midcoast community.

Maine: Belfast

Why we love it: The town has a palpable hippie-meets-hipster energy.
Where to stay: The retro Seascape Motel and Cottages brings a touch of Moonrise Kingdom–era Wes Anderson whimsy with its float-filled pool and impressive library of vinyls.

Belfast was once known for shipbuilding, poultry plants, and sardine packing. Today its energy is best exemplified by the progressive Belfast Cohousing & Ecovillage, the bustling United Farmers Market of Maine, and businesses like Chase’s Daily, a family-run flower farm, bakery, and vegetarian restaurant. Save time for a screening at the Colonial Theatre, which had its first screening the day the Titanic set sail; it reopened in November after a 14-month closure—with its green, pink, and purple facade and rooftop fiberglass elephant still intact. There’s a Laotian restaurant (Laan Xang Cafe) to add some spice to the traditional lobster shacks, and the Only Doughnut, which serves the state’s traditional potato doughnuts. For the best view of the waterfront, book a wooden rowboat tour with Nicolle Littrell of DoryWoman Rowing.

Green Ben and Jerry's ice cream truck, an old VW van, parked on grass — Nowadays, ice cream lovers can visit the Ben & Jerry’s Factory for a tour.

Vermont: Waterbury

Why we love it: Its culinary offerings skew decidedly more interesting than simply Cherry Garcia.
Where to stay: The Old Stagecoach Inn opened in 1826 and has served as a tavern, a stagecoach stop, a private residence, and a boarding house in its past lives.

The start of the scenic Green Mountain Byway, Waterbury is perhaps best known to casual visitors as the home of the Ben & Jerry’s Factory. And while the ice cream is so beloved in these parts that there’s even a graveyard of retired flavors, there are other reasons to plan a food-focused weekend here. Try Hen of the Wood, where dinner might include crispy skate cheeks with cider aioli or hanger steak with sourdough béchamel; Prohibition Pig, with its smoked meats and around-the-corner brewery; Zenbarn, which doubles as a live music venue; and Freak Folk Bier, which specializes in oak-fermented, mixed-culture beers. The town was badly battered by a once-in-a-generation flood last summer, so your dollars will go a long way toward helping local businesses recover. North of the historic district is Little River State Park, which includes the remnants of an old pioneer town and a Civilian Construction Corps–built reservoir where you can go boating, swimming, or fishing for bass and trout.

Aerial view of fall foliage from the hillside of Sugar Hill — You don’t need to be a skier to enjoy the views of Sugar Hill.

New Hampshire: Sugar Hill

Why we love it: For the chance to ski—or relax—in a mountainous part of the Northeast
Where to stay: Butternut Lodge, a three-bedroom cottage built in 1940 by Bette Davis, who spent summers here after falling for and marrying Peckett’s assistant manager Arthur Farnsworth.

Sugar Hill was only incorporated in 1962. Before then, when it was part of neighboring Lisbon, it was home to the country’s first resort-based ski school, Peckett’s on Sugar Hill, where Austrian-born Sig Buchmayr began teaching the East Coast elite about Europe’s cool newfangled way to get down a mountain. These days, Sugar Hill is a place to take it slow, whether you’re picking up a block of the beloved white cheddar from Harman’s Cheese & Country Store or grabbing breakfast at the 86-year-old Polly’s Pancake Parlor, which has been named an America’s Classic by the James Beard Foundation. The best time to explore this stretch of the western White Mountains is in June, when the surrounding hills come alive with lupine and the wildflowers are celebrated with an annual festival.

Two-story red brick building with the words "Hotel Connor" at top corner — Jerome is located around 100 miles north of Phoenix.

Arizona: Jerome

Why we love it: It’s an artfully repurposed old mining town built on red rock cliffs.
Stay here: Jerome Grand Hotel recaptures the magic of this historic mining town with its Spanish mission–style architecture, original 1926 Otis elevator, and abundant antiques.

Sedona grabs the headlines with its red-rock scenery and exciting art scene, but Jerome shares the same colorful sunsets, and ups the ante with a fascinating ghost-town history 40 minutes away. Built on the side of Cleopatra Hill—for easy access to what was once the state’s largest copper mine—the old buildings overlooking the Verde Valley now house hotels, restaurants, and galleries. The hilltop Jerome Grand Hotel repurposes the old hospital, while the century-old high school operates as a contemporary arts center. Over the past decade, the town has also grown a wine scene, which includes Tool frontman Maynard James Keenan’s Caduceus Cellars. Caduceau isn’t just star-powered: It has won awards many international wine contests, including the Los Angeles International Wine Competition and Las Vegas Global Wine Awards

Two people skiing, with evergreens in background — Skiers should consider heading to this town of around 2,500.

Colorado: Leadville

Why we love it: The scenic high-altitude haven features phenomenal hiking, skiing, and mountain culture with a spicy past.
Stay here: Freight has transformed a historic train depot and lumber yard into an inclusive, queer-friendly wedding venue with a collection of cabins inspired by the town’s mining history—and its notorious former red-light district.

Situated between Colorado’s Mount Elbert and the appropriately named Mount Massive, Leadville defines mountain-town culture. Miles of hiking, biking, and groomed cross-country trails keep people moving despite the 10,000-foot altitude—which makes it one of the highest incorporated cities in North America. (For those who prefer an assist on the uphill, Ski Cooper offers day passes for around $95.) With the most museums per capita in the state, including the House with the Eye Museum and the National Mining Hall of Fame, the town takes pride in its history, long drawing wealth-seekers, adventure-hounds, and gunslingers—such as Doc Holliday, Unsinkable Molly Brown, and “Baby Doe” Tabor. The names of future millionaires and scandalmongers also show up on the buildings of historic downtown and in the monikers of rooms at 19th-century hotel Freight.

Person in a green lifeguard chair on a beach, where people are walking beside the lake — Sandpoint sits on the shores of Lake Pend Oreille, Idaho’s largest lake.

Idaho: Sandpoint

Why we love it: This town is an outdoor activity paradise from the top of Schweitzer to the depths of Lake Pend Oreille.
Stay here: Talus Rock Retreat sits a mile outside of downtown Sandpoint and includes such amenities as a movie theater, an outdoor pool, and a bass-stocked pond with paddle boats and fly-fishing.

From the top of Schweitzer Mountain, skiers coming to the Sandpoint resort can look out at Idaho’s largest lake before letting go down the wide slopes of the mountain’s 2,900 skiable acres. But this town of 9,000, at the tip of Idaho’s panhandle, 60 miles from the Canadian border, is not only a spot that’s ideal for its year-round seasonality but also a place to explore both land- and water-based activities. Pack your itinerary with gentle boat excursions on the nearly 150-square-mile Lake Pend Oreille, horseback rides up the 6,400-foot Schweitzer Mountain, and high-adrenaline mountain biking and snowmobiling.

Parked cars lining a main street with mountain in background — Whitefish is a year-round destination for plenty of travelers.

Montana: Whitefish

Why we love it: The chance to get peace, quiet, and incredible scenery, including Glacier National Park
Stay here: Good Medicine Lodge features made-in-Montana furniture in the guest rooms and a fortifying prehike breakfast that might include house-made granola and locally made jam.

Trees climb higher than the buildings, eagles occasionally swoop overhead, and sparkling snow-capped peaks protrude from the horizon over Whitefish, making this small town feel almost too picturesque. Thankfully, the laid-back ski town vibes and bustling Central Avenue—studded with fun independent shops sporting “Made in Montana” goods—showcase the state’s authentic version of this reality. Most visitors come for the proximity to Glacier National Park; the Blackfeet-owned Sun Tours gives guided tours from both sides of the Continental Divide. But nearby Flathead Lake—the largest freshwater lake west of the Mississippi—and the trails through the Whitefish Range expand the outdoor opportunities.

Ancient adobe dwellings Taos Pueblo, with green mountains in background — Ancient dwellings of UNESCO World Heritage site Taos Pueblo, believed to be one of the oldest continuously inhabited settlements in the USA

New Mexico: Taos

Why we love it: For its quintessential New Mexico vibes, from the adobe architecture to the green chile salsa
Stay here: Located 20 miles from the Taos Ski Valley, El Monte Sagrado Living Resort & Spa offers a place to relax with its hydrotherapy tubs, saltwater pool, and complimentary yoga classes.

Defined by the raw beauty of the Sangre de Cristo mountains and Rio Grande Gorge, Taos exudes healing with its high desert air, sitting at 7,000 feet above sea level. But while Taos shares a lot with other best small towns in the country—plenty of sun, a great ski resort, chill artistic vibes where silver and turquoise jewelry fills the local galleries—there is no mistaking the smell of sopapillas or the adobe buildings for belonging to any other state. Visitors can learn more about the history behind the building method at the Taos Pueblo, a UNESCO World Heritage site, where Indigenous people carry on their traditions and allow guests to visit the 1,000-year-old adobe homes.

Coral sand with ATV tracks leading into sinuous dune — Visiting Kanab’s coral-colored sand dunes at sunset is one of its many outdoor opportunities.

Utah: Kanab

Why we love it: Kanab’s movie-perfect scenery in a base for easy access to a trio of national parks
Stay here: Best Friends Roadhouse and Mercantile is the ultimate pet-friendly resort; it not only allows dogs and cats but also actively welcomes and pampers them with such amenities as a pet-washing facility, a fenced-in park with a splash area, built-in cubbies for snuggling, and available dog-walking for when you’re out exploring.

Perched just north of the Arizona border, in the stunning red-rock sandstone cliffs and sagebrush of the Southwest desert, Kanab’s landscapes have earned it a supporting role in 20th-century westerns like Gunsmoke. The town is perfect for those wanting to explore the vistas beyond the screen, sitting an hour’s drive from Zion National Park and 90 minutes from Bryce Canyon and Grand Canyon national parks. Closer to town, hikers can hit the Belly of the Dragon cave tunnel, the jaw-dropping rounded red-orange striations of the Wave (permit required), and the aptly named Coral Pink Sand Dunes State Park. Just south of town, the free Red Pueblo Heritage Museum offers an impressive array of donated artifacts from Indigenous communities and early settlers in the area.

Brown and cream facade of vintage courthouse in the western town of Virginia City, Nevada — Virginia City is about 25 miles south of Reno.

Nevada: Virginia City

Why we love it: Its healthily kitschy and wholehearted embrace of its boom town past makes history come alive.
Stay here: A 1950s train car–turned–guest suite, Ruby the Red Caboose is available to rent on Airbnb, and it offers a private covered deck and a cupola from which you can take in 100-mile views.

The discovery of the Comstock Lode in 1859 was the first silver ore found in the United States, and the money it made built Nevada and much of California. Virginia City flourished, and this town in northwestern Nevada continues to mine the lode, although today for its history and stories. The Chollar Mine’s slogan was the “richest place on earth” (thanks to gold and silver there), and guided tours explain the historic buildings in town. While the 15 museums, comedy show, and even the bars all emphasize the history, the hillside cemetery offers another way to explore the legacy in this fascinating corner of the state. The elaborate graves, some made of marble and many with their own fences, show off the divisions of the town, with sections for people of different races, classes, fraternal organizations, and religions. Visitors can also ride on the century-old Virginia & Truckee Railroad steam engines and diesel locomotives that run from the town’s original 19th-century depot.

People sitting in stands at outdoor rodeo, with mountain in background — If you stop by Cody, Wyoming, be sure to catch a rodeo.

Wyoming: Cody

Why we love it: Travelers can celebrate art, rodeo, and the Old West a two-hour drive from Yellowstone.
Stay here: K3 Guest Ranch Bed & Breakfast sprawls across a 33-acre private valley between two trout streams and is also home to a bevy of barnyard animals, including Zip the trick pony and Pepper the mini-mule.

Buffalo Bill Cody opened his stage show here at the end of the 19th century to take advantage of the impressive scenery, excellent hunting, and steady stream of people heading into nearby Yellowstone National Park. More than a century later, these still bring folks to his eponymous town, as do the world-class fishing and the attractions opened by Cody himself. Five museums make up the Buffalo Bill Center of the West, including the wildlife-focused Whitney Western Art Museum and the Buffalo Bill Museum (which features exhibits dedicated to his relationship with Native Americans and his Wild West show). The original spirit of the town is carried on by nightly rodeos and tours of the historic local buildings. For a more somber side of the region’s history, the Heart Mountain Interpretive Center focuses on the Japanese incarceration center that operated there between 1942 to 1945.

People walking in front of a red barn store on a street — Traveling between Anchorage and Denali National Park? Consider a stop in Talkeetna.

Alaska: Talkeetna

Why we love it: A place to catch the northern lights and a peek at remote Alaska life near the base of Denali
Stay here: Alaskan-owned and operated Talkeetna Cabins has cabins and a log house a block from Talkeetna’s main street.

This dot on the map, two hours from Anchorage, sits about 60 miles from Denali mountain. It started as a supply town for rushing gold miners, steamboats, and then railroad workers, but today most visitors come on their way to climb, fly around, or simply admire North America’s tallest peak. On Main Street and elsewhere, people lean into Alaska’s reputation for oddity, as in Talkeetna Roadhouse’s use of a sourdough starter from 1902, and Hurricane Turn Train’s flagstop system—it stops anywhere along its route, taking signals from the wave of a flag. Travelers who luck out on timing also get a stellar view of the aurora borealis.

White exterior of Inn at Mattei's Tavern in background, with garden plots in foreground — The Inn at Mattei’s Tavern is located on the grounds of a former coach stop.

California: Los Olivos

Why we love it: This rare gem includes a walkable wine community, world-class cuisine, and luxury amenities
Stay here: The Inn at Mattei’s Tavern originated in 1886 as a stagecoach stop before becoming a Prohibition-era hangout and, much later, an elegant member of the Auberge Resorts Collection.

Located about a 45-minute drive northwest of Santa Barbara in the Santa Ynez Valley, the wine town of Los Olivos gained a bit of fame when it was featured in a number of scenes in Sideways. In the past two years, it welcomed luxury hotel the Inn at Mattei’s Tavern and seafood restaurant Bar Le Côte from the team behind the Michelin-starred Bells in nearby Los Alamos, adding to the town’s draw—and demonstrating its innate appeal to seekers of the finer things in life. More than two dozen wineries like Holus Bolus and Samsara Wine Co. pour their pinot noirs (and more) around town, which allows visitors to forgo finding a designated driver and relax into the cooling breezes of the Santa Ynez Valley and chill of the local chardonnays.

Woman in a white cowboy hat across from a man at outdoor produce and flower stand — Learn about Hawai‘i’s *paniolo* culture in Waimea.

Hawai‘i: Waimea

Why we love it: The verdant Hawaiian highland perch offers easy access to the best of Hawai’i Island.
Stay here: The Kamuela Inn nods to the upcountry’s cowboy heritage with design elements like horseshoes and barn doors.

Twenty minutes straight up from the heat of the white-sand beaches along Hawai‘i’s Kohala Coast, Waimea’s refreshing breezes complement its cool, laid-back culture. Three thousand feet above sea level and at the base of imposing volcano Maunakea, Waimea nourishes Hawai‘i’s paniolo (cowboy) culture with historic and working ranches. Visitors can get a feel for the culture by taking a spin on horseback with Paniolo Adventures or Kahua Ranch, or during the summer rodeo or fall Paniolo Parade. The culinary scene in Waimea also makes good use of that cattle—at the weekly farmers’ markets and at Waimea Butcher Shop, which has brisket sandwiches on ‘ulu bread and pipikaula, local seasoned dried beef.

Woman midair on a windsurfing board on Columbia River, with three other windsurfers in background — The Columbia River Gorge is one of the most popular places in the country to windsurf.

Oregon: Hood River

Why we love it: World-class wind and wine fill the Columbia River Gorge with envelope-pushing experts of all sorts.
Stay here: The owners of Sakura Ridge Farm & Lodge raise sheep and chickens and grow pears and apples for their award-winning ciders and perries.

Enthusiasts of adventure sports and artisanal foodways find common ground at Hood River, where the Columbia River Gorge funnels ferocious winds across the water and glacial runoff feeds the fertile valley. This intersection of the Cascade Mountains and the mighty Columbia creates a base for kiteboarders, mountain bikers, and skiers who also want to spend time sipping biodynamic wines at Analemma Wines and tasting through paired courses at Hiyu Wine Farm. In the ’80s, Hood River’s Full Sail Brewery—named for the windsurfers on the river—pioneered the craft beer movement, and today Pfreim Family Brewers still pushes the industry forward with experimental combinations of Belgian and Pacific Northwest brews.

Two- and three-story buildings in distance, viewed from water — Langley is located on Whidbey Island’s southern half.

Washington: Langley

Why we love it: The quiet island town offers a striking seaside setting, perfect for scarfing down fresh seafood.
Stay here: At the Inn at Langley, each guest room has water views, and the 22-seat restaurant serves pristine Pacific Northwest seafood.

Thanks to Langley’s perch on the bluffs overlooking the Saratoga Passage, diners slurping fresh local oysters could luck out and spot an orca or two over moules marinières or clams and chorizo. Green space lines one side of the main street as it follows the curve of the waterfront of Whidbey Island, and galleries and boutiques line the other. On any given night, a musician might play guitar in Seawall Park for the families in line while waiting for locally made ice cream and a pup cone at Sprinklz Ice Cream Parlor while brave swimmers take the stairs leading down to the shore. Impressive animals abound in Langley, in the air, like the local population of bald eagles, and on the plate, as in the famed Penn Cove mussels from the northern tip of Whidbey that grace nearly every menu on the island.

People with shopping bags beside veranda of two-story building with a U.S. flag hanging out front — Dahlonega’s history with gold traces back to the 1820s, when the mineral was first discovered in the area.

Georgia: Dahlonega

Why we love it: For its wineries, waterfalls, and the chance to strike it rich
Stay here: The seven rooms at Mountain Laurel Creek Inn & Spa feature gas fireplaces, jetted tubs, and private balconies. An on-site wine bar and spa lend an air of sophistication.

If the picturesque streets of this north Georgia town look familiar, you may be a closet Hallmark fan; the 2016 rom-com hit Christmas in Homestead was filmed here. While the town of 6,654 goes all out at the holidays with its six-week Old Fashioned Christmas celebration, it’s a year-round destination thanks to its fascinating gold rush heritage and its proximity to the southern terminus of the Appalachian Trail, about 20 miles away. Make the rounds to the tasting rooms of local wineries (Cavender Creek, Accent Cellars, Wolf Mountain); pan for your retirement at the Consolidated Gold Mine or Dahlonega Gold Museum; or spend an afternoon scouting area waterfalls. The 729-foot cascade in Amicalola State Park is particularly memorable—not to mention the tallest falls in the state.

Wite pelicans on shallow water, with others flying above — Birders can spot species like pelicans, herons, and cormorants in Cedar Key.

Florida: Cedar Key

Why we love it: This town is full of pristine estuaries and artist co-ops.
Stay here: Low-Key Hideaway is a funky dockside motel and RV campground with its own tiki bar and food truck. The property is pet-friendly but human visitors must be 21 and up.

Puttering around in a golf cart is one of the faster fun ways to explore this breezy Gulf Coast town of 700 residents. Once a hub for cedar pencil mills, the Cedar Key of today is better known for laid-back art galleries (check out Cedar Keyhole Artists Co-Op), fresh seafood (try the clams at Southern Cross Sea Farms), and abundant kayaking and paddleboarding opportunities (rent gear from Cedar Key Adventures). Located on the Great Florida Birding and Wildlife Trail, it’s ideal for watching wildlife, too: Bald eagles, osprey, gopher tortoises, and endangered salt marsh voles can be spotted at the Cedar Key Scrub State Reserve and Lower Suwannee National Wildlife Refuge.

Aerial view of water surrounded by green trees and distant mountains — Black Mountain sits at an elevation of more than 2,400 feet.

North Carolina: Black Mountain

Why we love it: For its whimsical galleries, live music, and layer-cake mountain views
Stay here: The Monte Vista Hotel offers around 50 rooms, and its restaurant Milton’s Black Mountain serves up seasonal cuisine reflective of the region.

Set in the painterly Blue Ridge Mountains, this folksy town of around 8,500 is only a 20-minute drive east of Asheville but feels a world apart. After ambling around Lake Tomahawk or hiking the 9.5-mile, out-and-back Graybeard Trail in nearby Montreat, enjoy a weaving or pottery exhibit at the Black Mountain College Museum + Arts Center, shop for handcrafted jewelry and candles at Seven Sisters Craft Gallery, or go into carb-load overdrive at the Blue Ridge Biscuit Company. However you fill your day, there’s no finer way to end it than with a wild session IPA from Blk Mtn Brewing and an old-timey Appalachian jam session at the not-for-profit concert venue White Horse Black Mountain.

Aerial shot of a marina with small boats docked — Paris, Tennessee, was established in 1823.

Tennessee: Paris

Why we love it: Travelers can get catfish buffets and pastries with a purpose.
Stay here: Antique furnishings and fireplaces make Home Sweet Home Bed & Breakfast one of the cozier places to bed down.

Paris, Tennessee’s biggest claim to fame isn’t its 70-foot replica of the Eiffel Tower. It’s the fact that the town of 10,000, two hours west of Nashville, is home to the world’s biggest fish fry—an all-you-can-eat affair usually scheduled for the last week in April. Late March through May, meanwhile, is crappie and bass season at Paris Landing State Park, where visitors can also swim, golf, hike, or ogle the coots and cormorants flanking its paved picnic loop. Also noteworthy: Paris City Cemetery, final resting place of John Wesley Crockett (1807–1852), the state attorney general and son of Davy Crockett, and Sweet Jordan’s, a bakery founded by Jordan St. John, a young man with Down syndrome who hires staff with special needs.

A table of six toasting glasses outdoors, with trees in background — Fredericksburg’s downtown has more than 150 local shops.

Texas: Fredericksburg

Why we love it: For wine, wine, and more wine
Stay here: Lock in a rustic 19th-century cabin or crisper cottage at Cotton Gin Village, a B&B-style property kitted out with koi ponds, waterfalls, and firepits.

While Greater Lubbock grows 90 percent of Texas’s grapes, the Hill Country American Viticultural Area (AVA) is an easier weekend getaway for visitors to San Antonio and Austin. Base yourself in Fredericksburg to experience Messina Hof, the most awarded winery in Texas; the full-bodied Argentinean-style reds at the boutique-y Santamaria Cellars; and the surf-and-turf menu at Cabernet Grill, named one of the top U.S. wine restaurants by Wine Enthusiast for its Texas-exclusive wine list. If time permits, learn about Fredericksburg’s early German settlers at the sprawling Pioneer Museum or go boot scootin’ at the Luckenbach Texas General Store, Bar & Dance Hall.

Three men playing music on a stage, with drums, accordion, and metal washboard — Enjoy crawfish with a side of zydeco music in Breaux Bridge.

Louisiana: Breaux Bridge

Why we love it: Visitors can indulge in everything from crawfish boils to Zydeco parties.
Stay here: Suites and cottages at the veteran-owned Country Charm Bed & Breakfast overlook a privately stocked fish pond; anglers can release their catch or cook it in the outdoor kitchen.

Thousands of seafood-crazed visitors descend upon the town of Breaux Bridge, aka the “Crawfish Capital of the World” and birthplace of crawfish étouffée, for its annual Breaux Bridge Crawfish Festival each May, but the culinary darling of St. Martin Parish offers good eating all year long. Hit up Poche’s for pork backbone stew and smothered rabbit or Cajun Claws for down-home seafood boils, then work it off two-stepping across the thundering hardwood floor at La Poussiere, a 69-year-old dance hall soundtracked by live Cajun and Zydeco bands. For fresh air, go birding and gator spotting at the swampland preserve of Lake Martin or paddle through the cypress-rich canoe country of Atchafalaya National Wildlife Refuge.

Aerial view of large hotel surrounded by fall foliage — Eureka Springs gets its name from the natural springs in the area.

Arkansas: Eureka Springs

Why we love it: For spirituality with a side of rescue tigers
Stay here: A Victorian parlor and outdoor hot tub are two of the selling points at 5 Ojo Inn, a four-star bed-and-breakfast with nine elegant guest rooms.

This resident town of 2,000 already draws Christians with its 67-foot-tall Christ of the Ozarks statue, modeled after Rio de Janeiro’s Christ the Redeemer, and annual outdoor staging of The Great Passion Play. But there’s more to this corner of the Ozarks than a Bible Museum. Downtown Eureka Springs is listed on the National Register of Historic Places: admire the preserved Victorian architecture and make special note of Hatchet Hall, the former clapboard home of hatchet-wielding temperance movement leader Carry A. Nation, and the Palace Hotel and Bath House, which harkens back to Eureka’s glory days as a Victorian-era hot springs boom town. The outskirts deserve a gander too. Turpentine Creek Wildlife Refuge provides a forever home to abandoned, abused, and neglected big cats, while the tranquil Thorncrown Chapel, a soaring wood-and-glass sanctuary designed by architect E. Fay Jones, inspires quiet meditation—no matter your religious affiliation.

Horse-drawn blue carriage in front of a white house — Beaufort is the second oldest city in South Carolina.

South Carolina: Beaufort

Why we love it: Visitors can get a taste of Gullah Geechee music, storytelling, and food traditions
Stay here: The Rhett House Inn oozes Southern glamour with its wraparound veranda, homemade cookies, and complimentary beach chairs and bicycles.

The antebellum mansions and towering oaks lining the streets of Beaufort have serious Hollywood cred: The Big Chill, The Prince of Tides, and Forrest Gump were all filmed here. For travelers, the appeal goes even deeper. Notable landmarks such as the 226-year-old Arsenal on Craven Street, with its rich and varied military past, and the John Mark Verdier House, the city’s only planter’s house open to the public, enchant history buffs, but Beaufort also has a strong Gullah Geechee influence. Learn how descendants of enslaved Africans brought to the coastal areas of the Sea Islands and Lowcountry have preserved their unique language and culture through a Gullah Heritage Trail Tour or Gullah-N-Geechie Mahn Tour of Hilton Head and St. Helena islands, respectively. To round it out, sample gumbo, fried okra, and other Gullah dishes at the Gullah Grub or Sandies at the Gullah Jazz Cafe.

Horses in a fenced-off area, with people taking pictures on other side of fence — Chincoteague is located on Virginia’s island of the same name.

Virginia: Chincoteague

Why we love it: For Chesapeake Bay seafood and wild pony swims
Stay here: The family-owned Refuge Inn has 70 rooms and suites, a pool, hibachi grills, and a beach reads lending library—not to mention it’s 13 minutes to NASA’s Wallops Flight Facility.

Chincoteague is the gateway to Assateague Island National Seashore, famed for its red-and-white-striped lighthouse and wild ponies that have roamed this land for centuries. Tourists flock to the town every July for the Chincoteague Island Pony Swim, where equines are herded across the channel, and to traverse the untouched Chincoteague National Wildlife Refuge, a haven for migratory birds and waterfowl, including osprey, great egrets, and piping plovers. Swimming and beachcombing are popular pastimes, or you can explore the marshes and coastal waterways via kayak or canoe. (If you’re extra lucky, you might spot dolphins.) Clam strips and crab-stuffed onion rings are on the menu at the seasonally operated Capt. Zack’s Seafood, or you can delve into locally harvested oysters at Ray’s Shanty, an Eastern Shore staple since 1986. Come nightfall, head back to the beach for a little Milky Way magic: With inky black skies, Chincoteague is a top-ranking destination for East Coast stargazing.

Wall of small, framed photos of people above shelf of books at bookstore — Oxford is home to the University of Mississippi.

Mississippi: Oxford

Why we love it: Ample opportunity for epic eating and a lively arts and culture scene
Stay here: The four-star Graduate Oxford hotel puts a hip spin on university-inspired digs—and is conveniently located within walking distance of Ole Miss.

Oxford ranks among the largest towns on our list at a little over 25,000, but its vibrant literature and art worlds are as intimate as they come. Tour the museum at Rowan Oak, the former home of Nobel Prize–winning author William Faulkner; attend a live recording of Thacker Mountain Radio Hour, a radio show featuring weekly author readings and musical performances; and load up on local titles at Square Books, a 45-year-old bookstore set on historic Oxford Square. See what’s on tap at the Powerhouse, a community arts center whose diverse programming spans cocktail competitions and second-line concerts, or time your visit to one of the city’s renowned festivals, such as the two-day Double Decker, which encompasses food, music, and art. Whatever you get up to, you’ll never go hungry: From the James Beard–caliber dishes at Saint Leo to down-and-dirty country-fried steak plates at Ajax Diner, Oxford delivers.

People riding horses and herding cattle on a street, with people on sidewalks watching — Tuscumbia, Alabama is located along the Tennessee River.

Alabama: Tuscumbia

Why we love it: It’s a place for learning about musical legends, literary icons, and Civil Rights role models.
Stay here: Seven Springs Lodge rents cabins, silos, and campsites and even has stalls for horses if you bring your own. Don’t miss the watering hole Rattlesnake Saloon, squirreled beneath a dramatic rock overhang.

The birthplace of Helen Keller attracts literature fans and equal rights advocates from around the world, and not just to tour the Keller family home. Visitors to this northern Alabama town spend their time strolling the verdant walking trails of Spring Park (where a 51-jet fountain shoots water 150 feet high) and scouting falls at Cane Creek Canyon Nature Preserve. Also worth the visit: Alabama Music Hall of Fame in nearby Muscle Shoals and Tuscumbia Elementary School, which, in 1963, became the first public school in the state to integrate Black students.

Aerial view of river valley, with forested mountains and a strand of fog — Fayetteville, West Virginia, is a fantastic base for those exploring the New River Gorge National Park.

West Virginia: Fayetteville

Why we love it: This small town provides a million ways to get outside.
Stay here: The 14-room, Queen Anne–style Historic Morris Harvey House has seven fireplaces and two antique bathrooms with original clawfoot tubs. More importantly, it’s only 2.5 miles from New River Gorge National Park.

Fewer than 3,000 people call Fayetteville home, but the town has seen an uptick in visitors since the rugged New River Gorge National Park and Preserve was named the nation’s 63rd federal park in 2020. Whitewater rafters, rock climbers, and mountain bikers have succumbed to its magnetism for decades, but the rest of the world is waking up to this uniquely biodiverse area—its forest alone nurtures more than 1,500 species of plants. For sweeping canyon views, aspiring photographers usually make a beeline for the New River Gorge Bridge, one of the longest single-span arch bridges on Earth, while hikers book it to the Endless Wall Trail, a moderate 2.4-mile trek that zags along vertical sandstone cliffs. Fayetteville proper has plenty to woo less outdoorsy types, too, including breweries (Bridge Brew Works, Freefolk Brewery) and artisan-first shops such as Studio B and Lost Appalachia Trading Co.

Aerial view of historic red-brick building in the middle of a roundabout — Come to Bardstown in September for its Kentucky Bourbon Festival.

Kentucky: Bardstown

Why we love it: The place to go for bourbon, bourbon, and more bourbon
Stay here: Turkish towels, terry bathrobes, and other luxe touches abound at Bourbon Manor, the world’s first bourbon-themed bed-and-breakfast.

The so-called Bourbon Capital of the World has more going for it than booze, though obviously that’s a big lure: Good luck getting out of town without paying a visit to Maker’s Mark, Heaven Hill, Willett, Barton 1792, or one of the other distilleries dotting its rolling blue-green hills. The newly renovated Oscar Getz Museum of Whiskey History does a fantastic job chronicling the production of whiskey in the USA, while the 90-minute Bardstown Ghost Trek dips a toe into the darker side of tavern life. For families with kids in tow, there’s nothing better than bellying up to the century-old soda fountain at Hurst Discount Drug for an old-fashioned malt or banana split.

White pedestrian bridge over a calm river, with a few houses in background — Founded in 1908, Medicine Park is located by Lake Lawtonka.

Oklahoma: Medicine Park

Why we love it: For its cobblestone downtown and access to the Wichita Mountains
Stay here: Learn to appreciate the little things in life by booking a guest room housed within a repurposed shipping container at InnHabit, Oklahoma’s only tiny house resort.

With just under 500 full-time residents, Medicine Park’s distinctive streets are lined with nationally registered cobblestone buildings, constructed using granite from the Wichita Mountains. For a closer look at said peaks—plus a chance to see Rocky Mountain elk, American bison, and prairie dogs—drive the three-mile Wichita Mountains Scenic Byway. The thoroughfare winds through the Wichita Mountains Wildlife Refuge, a spot beloved by hikers, rock climbers, fishermen, and stargazers. (The refuge is a designated Dark Sky Park.) Back in town, visitors can order hot-from-the-oven cinnamon rolls at Mrs. Chadwick’s Bakery and then head over to Bath Lake, a century-old granite swimming hole sustained by the waters of Medicine Creek.

The tall Steuben County Soldiers Monument in roundabout in downtown Angola, with the red-brick buildings in background — Angola, Indiana, was founded in 1838.

Indiana: Angola

Why we love it: Communal breweries, easy access to lakes, and university energy
Stay here: In a sea of chain hotels, this two-bedroom lakefront guest suite stands out with its outdoor hammock, firepit, and souped-up chef’s kitchen. (It even has a margarita maker!)

Northeastern Indiana is blessed with more than 200 serene lakes. The laid-back town of Angola, in particular, is within a 15-minute drive of Crooked Lake, Lake James, and Pokagon State Park’s waters, a destination for kayaking and fishing. After all that outdoor adventure, head into town and peruse the antique shops lining historic Maumee Street or toast a piney single hop IPA at beloved Chapman’s Brewing Co. For events lining up to your visit, check the calendar at Trine University, the largest employer of the town and a large driver of the social scene here. Upcoming events can be anything from a hockey game to an intimate concert with “American Pie” singer-songwriter Don McLean.

Cars and small businesses line a street of historic wood and brick buildings — Galena’s downtown has more than 100 art galleries, boutiques, and restaurants.

Illinois: Galena

Why we love it: Its jam-packed Main Street with historical experiences to boot
Stay here: Some rooms at Irish Cottage Inn & Suites have jetted tubs and wet bars, but it’s the afternoon tea served in the Irish library and the scotch eggs with Guinness at the cozy-dark pub that keep guests coming back.

Galena (named after the mineral) sits in the state’s northwestern corner and was built on the mining industry in the 19th century. Today, its downtown has developed into a center with more than 100 places for shopping, eating, and wandering. Look for tarot cards and divination candles at A Darkness Lovely, sister store of the Haunted Galena Tour Company, and wooden utensils and farmhouse paddles at Galena Spoon Co. before sipping a root beer float at Root Beer Revelry, home of the world’s only public Museum of Root Beer. There’s a historic side to Galena, too: Cross the scenic Galena River to tour the former residence of Civil War general and former U.S. President Ulysses S. Grant. Anyone seeking a century-old forge in action can swing by the Old Blacksmith Shop.

Side view of a brown horse pulling a white carriage in front of a blue and white building with porch — Frankenmuth was settled in 1845 by a group of German immigrants.

Michigan: Frankenmuth

Why we love it: An over-the-top connection to Christmas and strong Germanic roots
Stay here: The 360-room Bavarian Inn Lodge does a fine job channeling that Deutschland spirit, though the Euro-style courtyard is decidedly Midwestern with its splashy indoor waterpark.

The first thing visitors probably notice about Frankenmuth is its Bavarian-inspired, timber-framed architecture. If a chicken dinner at the 136-year-old Bavarian Inn Restaurant or the lebkuchen from the bakery at Zehnder’s don’t clue you in, its German touches are beyond aesthetic. This town of some 5,000 residents was settled by Germans in the 19th century, which visitors can learn more about aboard the Bavarian Belle, a two-story paddlewheel riverboat that cruises along the Cass River, or during the German-themed parades, keg tapping, and wiener dog races of its Oktoberfest. Don’t forget to stop by Bronner’s Christmas Wonderland, which was founded in 1945 and, at 27 acres, is billed as the world’s largest Christmas store. (It’s also open 361 days a year.)

Person in front of a red and yellow fair food stand selling funnel cakes, corn dogs, and soft drinks — Yellow Springs, Ohio, is home to plenty of events, including its biannual street fair.

Ohio: Yellow Springs

Why we love it: The town has a free-spirited liberal arts atmosphere with ace outdoor rec.
Stay here: The apartment-style Tower at Jailhouse Suites is in what served as the town jail from 1878 until 1929. All that remains of the original cells are some bars on windows.

If you get a distinctly bohemian vibe bouncing around the artisan-focused pottery shops, excellent bookstores, and internationally minded restaurants (Caribbean! Taiwanese Israeli Indian!) of this southwestern Ohio town, you have Antioch College to thank. The school has long been a hub for environmental activism and social justice—a sentiment that has spread throughout this town of 3,702. Look to the Yellow Springs Arts Council for fascinating gallery shows and cultural events, Little Art Theatre for indie movie screenings, and Yellow Springs Brewery for pints with a side of progressive politics. To soak up the four seasons, tackle a cliff-side hiking trail at the 752-acre John Bryan State Park, keeping your eyes peeled for chimney swifts and red-tailed hawks, or pick up a leg of the multi-use Little Miami Scenic Trail, which runs for 78 miles and intersects with the Clifton Gorge State Nature Preserve.

Red wooden building alongside a creek, with forested hills in background — The fertile land around Viroqua, Wisconsin, makes it a top place for fresh food.

Wisconsin: Viroqua

Why we love it: This pastoral escape has an eye on sustainability and farm-to-table eating.
Stay here: The Scandi-modern Tanager cabin at Driftless Creek, enveloped by thick woods a few miles outside of town, has a Norwegian wood-burning stove and musical instruments hung on its walls.

Fly-fishing streams and Amish farms are scattered throughout Wisconsin’s Driftless Area (a term referring to the southwest part of the state that went unglaciated 10,000 years ago). But Viroqua proper is a hotbed of culinary creativity, in part thanks to the more than 200 organic farms located in the area. Tuck into a savory biscuit sandwich from Wonderstate Coffee, a solar-powered roastery and fair-trade café housed in a 1940s gas station, or settle in for a meal at the Driftless Café, where co-owner and PBS host Luke Zahm draws his bounty from the hundreds of organic farms dotting Vernon County. For dessert, ice cream and crepes await at Magpie Gelato, or you can cobble together your own Dairyland cheese plate from the vaunted Viroqua Food Co+op. On a rainy day, browse the stacks at Driftless Books & Music, one of the state’s largest used bookstores; if the sun is shining, take a DIY tour of Viroqua’s myriad murals or stop by the Driftless Angler fly shop to book a guided trout-fishing lesson.

Canoeist on a canoe, viewed form back, on a remote lake in Minnesota, with tall evergreens on banks — Explore the “Land of 10,000 Lakes” in the Boundary Waters Canoe Area near Ely.

Minnesota: Ely

Why we love it: For canoeing, dog sledding, and a Northwoods-centric folk school
Stay here: Moose Track Adventures can arrange guided canoeing and fishing outings or leave you be in one of its six comfy cabins, complete with charcoal grill, stone fire pit, and private dock access.

Cozied up to the Canadian border, Ely is best known as the gateway to the Boundary Waters Canoe Area Wilderness, a million-acre reserve of interconnected rivers, lakes, and forest. The town also boasts the world’s highest concentration of dog sled outfitters per capita. Test your mushing skills by signing up for a half-day fun run or challenging backcountry trek with Chilly Dogs Sled Dog Trips; the family-run operator counts dozens of retired racing dogs among its crew. While you’re in the canine spirit, pop by the International Wolf Center to meet its ambassador wolves and learn why wolf conservation is so important. Should time permit, Ely Folk School offers a range of immersive, skills-based classes: needle felting, willow carving, and animal tracking in snow among them.

A four-person band performs on a small outdoor stage, with audience in front — Time your visit to one of Kimmswick’s big community celebrations such as the strawberry harvest in June or the Apple Butter Festival in October—the latter draws more than 100,000 attendees.

Missouri: Kimmswick

Why we love it: It offers candy-sweet shops, lively festivals, and mastodon bones.
Stay here: Serenity Log Inn, a 1930s two-bedroom cabin a mile outside town, has a fireplace, screened-in porch, and modern kitchen and bath.

Situated on the banks of the Mississippi River, the wee town of Kimmswick is a half-hour drive from St. Louis. Spend time at the National Museum of Transportation’s Wabash, Frisco, and Pacific Railroad outpost to learn more about the trains that chugged through this town, which today is home to the Anheuser Estate, a 19th-century mansion formerly occupied by, yes, that Anheuser. Knock out some shopping at the Spicery of Kimmswick (try Miss Em’s Peruvian spice blend) and Mississippi Mud Gallery & Gifts before blowing your mind at Mastodon State Historic Site, the paleontological bone bed where scientists discovered the first concrete evidence of humans coexisting with North American mastodons.

Aerial shot of a community beside grass-covered plateaus — Fewer than 150 people live in Medora, North Dakota.

North Dakota: Medora

Why we love it: The scenic Badlands getaway is the place to go for cowboy musicals and barbecues.
Stay here: Rough Riders Hotel seamlessly blends the old (pressed tin ceilings, balconies where former presidents were rumored to have given speeches) and new (walk-in showers, a restaurant serving bison osso bucco).

Medora is one of the smallest towns on our list, but it’s the gateway to Theodore Roosevelt National Park in the staggeringly beautiful Badlands, an area that America’s 26th president says dramatically shaped his views on conservation. Watching the Old West–themed Medora Musical, an outdoor production at the Burning Hills Amphitheatre, is a must-do summer experience, as is witnessing the live-fire grilling of 12-ounce New York strip steaks at the town’s annual Pitchfork Steak Fondue. You can learn about the state’s ranching heritage at the North Dakota Cowboy Hall of Fame year round.

Bird's-eye view of a waterfall in the middle of a forest — Chase gorgeous waterfall, like Spearfish Falls, on a trip to Spearfish.

South Dakota: Spearfish

Why we love it: For its western heritage, offbeat art, and all things Black Hills
Stay here: Guests must be 21 and up to stay in one of the three secluded cabins at Rim Rock Lodge. An additional trio of suites is available in the main lodge—each with sweeping views of Spearfish Canyon.

There’s no better base for exploring the Northern Black Hills, including Mount Rushmore and Crazy Horse Memorial, than Spearfish. After checking off the aforementioned postcard sites and exploring Bridal Veil Falls in Spearfish Canyon, pay a visit to the D.C. Booth Historic National Fish Hatchery to get schooled on rainbow trout or the High Plains Western Heritage Center to get a fuller grasp of the rugged individualism that defined the American cowboy. But artsier travelers can find enriching experiences as well—pick up tickets to a cabaret show or bluegrass jam session at the Matthews Opera House & Arts Center or explore the op-art spherical paintings at Termesphere Gallery, the by-appointment-only showroom of artist Dick Termes.

Two red-brick buildings, with a few car parked in front of them — Aurora is located in Hamilton County, Nebraska.

Nebraska: Aurora

Why we love it: This small town has a lively downtown, hands-on science center, and pioneer gear galore.
Stay here: Built in the 1930s, the six-bedroom, two-bath Cyr House accommodates up to 10 guests and is walkable to the Square.

For a place with fewer than 5,000 residents, Aurora has a lively town center. The two-block radius around Central Park Square (known as the Square) includes a cinema, butcher shop, bookstore, flower shops, spas and salons, and a clutch of independently owned boutiques. Rath’s Cafe serves barbecued meatballs, ham salad sandwiches, and other comfort foods. Educational draws for families include Edgerton Explorit Center, one of the Midwest’s foremost experiential science centers (founded by the doc who invented the strobe light), and the Plainsman Museum, a 50,000-artifact-strong nonprofit focused on the life and times of pioneers. (Its special exhibitions include a one-room schoolhouse dating to 1874.) In the dog days of summer, children can enjoy the waterslides and lazy river at the Aurora Aquatic Facility and cool off with an Italian ice from JoJo’s Gelato & Grill—or join their parents for a fun-packed day at Pioneer Trails, a recreation area with trails for biking, hiking, and horseback riding.

Super moon rising Near a small, old, castle-like building made of stone. — If you visit Lindsborg, stop by the Coronado Heights Castle.

Kansas: Lindsborg

Why we love it: Travelers can take in Swedish-inspired art and architecture with a side of pickled fish.
Stay here: Set in a pink Queen Anne Victorian, the adults-only Rosberg House Bed & Breakfast has a swimming pool, gazebo with gardens, and five guest rooms available for full buyout.

Swedish immigrants founded this town of just under 3,500 in the late 1800s, earning it the nickname “Little Sweden, USA.” From the Birger Sandzén Memorial Gallery, honoring the eponymous Swedish American artist who lived and worked in Lindsborg, to the multilingual street signs and handcrafted Dala horses scattered around, the town is very much steeped in its history. Order pickled herring with knäckebrot at Öl Stuga, catch a performance by the Lindsborg Swedish Folk Dancers, or time your visit to Svensk Hyllningsfest, a biannual celebration of Lindsborg’s proud Scandinavian heritage, with music, food, and folk dancing. The Red Barn Studio Museum is another worthwhile stop, celebrating the folksy work of (non-Swedish) multimedia artist and toymaker extraordinaire Lester Raymer.

Wide, rocky waterfall in a forest — Decorah, Iowa, is located in northeastern Iowa.

Iowa: Decorah

Why we love it: For its craft beer, waterfalls, and heirloom seed-sharing program
Stay here: The former opera house at the historic Hotel Winneshiek has its original tin walls and ceiling, a grand stage, and a private dining room for special events. (The king suites with double whirlpool tubs are pretty swank, too.)

A part of the Upper Midwest’s bucolic Driftless Area, the 7,600-person town of Decorah inspires boundless outdoor exploration. Canoeing, kayaking, and tubing the Upper Iowa River and Cardinal Marsh are popular ways to get on the water, or you can chase waterfalls at Malanaphy Springs and Dunning’s Spring Park. Rent wheels from Decorah Bicycles and hit the 11-mile Trout Run Trail or sign up for a Nordfjord-style bowl-turning class at the Vesterheim Museum’s folk art school, capping your day with a beer (or three) at Pulpit Rock or Toppling Goliath Brewing. Green thumbs, take note: Decorah is home to the Seed Savers Exchange, a 49-year-old nonprofit seed bank and heritage farm dedicated to preserving and sharing heirloom seeds.

Left picture shows bowls of food on a dining table, right picture shows a storefront with the words "Bienvenidos Los Pinos" — Stop by Guavate for some good food, before considering a visit to the mountain municipalities of Caguas and Cayey.

Puerto Rico: Guavate

Why we love it: For its meat-filled goodness in the middle of the mountains
Where to stay: El Pretexto, a mini farm and bed-and-breakfast where you can wake up to sky-high mountain views and the crowing of a resident chicken named Santiago.

Drive about an hour south of Puerto Rico’s capital and you’ll land in Guavate, a town of around 2,000 in the central region of Cayey. Arrive hungry, because it’s where you’ll find la ruta de lechón, a snippet of Highway 184 dedicated to serving up lechón asado. The history of these restaurants depends on who you ask, but nonetheless this has become the place to eat pork. Try the dish at eateries like Lechonera Los Amigos and El Rancho Original before declaring a favorite, and enjoy the winding roads and mountain vistas that come with the territory.

Nicholas DeRenzo

Nicholas DeRenzo is a freelance travel and culture writer based in Brooklyn. A graduate of NYU’s Cultural Reporting and Criticism program, he worked as an editor at Arthur Frommer’s Budget Travel and, most recently, as executive editor at Hemispheres, the in-flight magazine of United Airlines. His writing has appeared in the New York Times, New York, Travel + Leisure, Condé Nast Traveler, Sunset, Wine Enthusiast, and more.