Ditch city life for the most charming small towns in the US.
Updated on July 17, 2024 at 2:46 PM
Where to go when the big city feels too big. | Sean Pavone/Getty Images
It’s no secret that we at Thrillist love to travel—in fact, it’s pretty much all we do. And with every new flight, mountain summit, cocktail bar, and hotel check-in, we always learn something new. That’s why we’re in the habit of turning to our team of seasoned editors and global contributors, each with extensive boots-on-the-ground experience, to help you plan your next jet-setting adventure.
The romanticism of small towns is part of America’s charm: the idyllic Main Street with its ice cream parlors and chocolatiers, cobbled roads only horses and pedestrians can pass through, streets sans stoplights and buildings capping out at two stories. When you fall in love with a small town, you fall hard. Even for us writers, it’s hard to avoid using clichés like quaint and charming—even if both of these adjectives are absolutely true.
We looked from coast to coast at villages, townships, and even islands, where the living is easy and the pace reliably slow. These spots are rich in comfort food and craft brews, music and artists, natural attractions and quirky roadside stops, and, best of all, free from big city distractions and crowds.
Of course, what qualifies as “small” is relevant (it’s often defined as a population of less than 5,000, but this can seem like a big city in some states or a hamlet in others). But all of these towns offer the same thing—a respite from big-city life, and, often, a gateway to outdoor adventure (which is why road tripping is part of the fun of getting here). Don’t be surprised if you find yourself scouring the real-estate listings—probably at a tiny little bakery owned by someone who also fell in love with the town and never left.
Population: 15,014
In the crown jewel of the Redneck Riviera and home of the annual Hangout Music Festival, there’s a lot more than music and good ole boys. This Gulf of Mexico beach town surprisingly boasts one of the best zoos in America, where encounters with animals like lemurs and monkeys are cheaper and last longer than at most. It also borders Gulf State Park, the best state park in Alabama, which lost its iconic zipline but added substantial bike trails. The city is also home to the state’s southernmost brewery, Big Beach Brewing, as well as one of the world’s best beachside burgers at Pink Pony Pub. —Matt Meltzer, travel writer
Population: 5,522
There are few things more magical than driving into Homer on a bluebird day. As you round the last corner on the Sterling Highway, the view out your windshield is a panorama of snow-capped mountains across the shimmering, boat-speckled Kachemak Bay and the long, skinny Homer Spit, the world’s longest road into ocean waters. In this quirky harbor town, you’ll find tons of galleries, dynamic local cuisine, fishing charters, a couple of good breweries (including the Salty Dawg Saloon), great hikes (on trails or glaciers), and so much more. It’s also a jumping-off point for flightseeing tours of Katmai National Park, home to around 2,000 brown bears. –Bailey Berg, travel editor
Population: 9,684
Arizona’s red-rock playground offers seriously breathtaking desert landscapes best enjoyed on a hike or a climb, and a walk around town mingling with kooky-but-kind locals. Take off your boots and zen out with a massage and guided meditation session at one of Sedona’s many spas, or binge on top-notch tamales from Tamaliza and gussied-up carne asada at Elote Cafe. When you start itching for a punchier after-hours scene, the very-hip Flagstaff is less than an hour down the road. —Melissa Kravitz Hoeffner, travel writer
Get Your Psychic Kicks in Arizona’s Trippiest Desert
Sedona’s mysterious energy vortexes are basically Disneyland for the New Age crowd.
Population: 2,166
Perhaps no tiny town in America is more things to more people. Bikers love it as a stop along mountain backroads; hippies love it for its low-key, California-transplant vibe. The town has passed some of Arkansas’s most progressive LGBTQ policies; it also contains the state’s two most famous Christian landmarks: a 66-foot-tall, arms-wide-open Jesus statue and architect E. Fay Jones’s nationally celebrated Thorncrown Chapel. The gingerbread architecture of many of the homes complements the stone-and-brick downtown, which prohibits chain stores and therefore thrums with mom and pop restaurants, taverns, and (albeit touristy) craft shops. Its little public library was donated by Andrew Carnegie a century ago, and it’s just a few minutes away from Beaver Lake, a summertime party hangout for boaters—and one of the better bass-fishing lakes in the Ozarks. —Sam Eifling, journalist
This Small Town in Arkansas Celebrates Pride All Year Round
If it’s a drag show you’re after, head to Eureka Springs, population 2,000.
Population: 7,637
There’s a reason this Ventura County oasis has long been a magnet for hippies, healers, and incognito rock stars sick of the constant hum of LA—the place is truly zen AF. On the outskirts, you’ll pass Johnny Cash’s old house as you spy sprawling orange groves that stretch deep into foothills lined with luxury hotels and ranches. Downtown, Mission-style architecture unfolds across a walkable hamlet packed with greenspaces and local haunts like the famous Bart’s Books; breweries like Topa Topa and Ojai Valley; and combination housewares shop and cheese-and-wine bar Tipple & Ramble, which brings a taste of the valley’s viticulture to a chill backyard setting. On Sundays, the entire town comes together for the Ojai Certified Farmers Market, a quintessential country fair—only at this one, you’re just as likely to spy a retired supermodel as you are the perfect basket of Ojai Pixie tangerines. —Andy Kryza, former Thrillist editor
This Laid-Back Mountain Town Is the Zen Reset You Need
Just 90 minutes from LA, put Ojai on your weekend agenda.
Population: 2,607
It’s kind of a pain to get to Telluride, but, oh, the rewards upon arrival. This former silver mining town hunkers basically in a dead-end valley, its mountains sporting one of the most gorgeous waterfalls in the world: Telluride’s Bridal Veil. With peaks great for skiing, mountain biking, or hiking, it’s about as sweeping as it gets. The town has blossomed into one of the best festival sites in the nation, with renowned events like the Bluegrass Festival and Telluride Film Festival. Even if you’re in town when a fest isn’t, you can grab a drink (or better yet, stay) at the historic New Sheridan Hotel, then continue your crawl to the no-frills Last Dollar Saloon before hitting 221 South Oak, a fine-dining spot helmed by Top Chef alum Eliza Gavin. —Colin St. John, travel writer
Population: 4,348
The pizza joint might be the most famous thing in Mystic to outsiders, but this old port town has so much more to offer than Julia Roberts references. And while tourists flock to Mystic during the summer to hang out at the wharf, gaze at the coastal architecture, and hit the aquarium, it’s the fact that the centuries-old village is so beautiful and laid-back in the offseason—when the barstools go back to locals and the docks empty out. It’s the quintessence of idyllic Rockwellian New England bergs that dot the landscape, here fine-tuned into paradise on the Mystic River. Oh, and the pizza at that Julia Roberts place? Not bad! —AK
7 Reasons to Drive to Mystic, Connecticut
Explore museums, a historic downtown district, and famed pizza spot at this maritime town.
Population: 3,303
Unless you grew up on a small stretch of the mid-Atlantic, you probably don’t know about the constellation of beach communities that make up Delaware’s southeastern shores. Hell, I didn’t know the state even had beaches until I fell in love with a Delawarean (yes, they exist) and started spending weekends in places like Dewey and Rehoboth. I was suspicious, being a California beach kid, but one summer in Lewes enchanted me for life. It’s the rare town that delivers on the promise of “something for everyone,” made better by the fact that they have a hotel run by the beer savants at Dogfish Head. (Their main brewery is a few miles down the road in Milton.) Local spots like Matt’s Fish Camp are synonymous with summer for Delawareans, and Heirloom would give any farm-to-table spot in Soho or Venice Beach a run for its money. —TM Brown, travel writer
Population: 318
The sister to larger Sanibel, Captiva is a wisp of an island 30 miles off the coast of Fort Myers that sports some of the best sand in the Sunshine State (there also aren’t any stop lights or buildings higher than the tallest palm tree, which adds to the beach town charm). Stretching just five miles long, Captiva’s “downtown” is like a much, much more laid-back version of Key West (think seafood shacks and kitschy, colorful Christmas-themed restaurants). On the drive from Sanibel, collect seashells in the sand bar at Blind Pass Beach (where the two islands connect) and stay as the sun goes down—this is when the island’s magic comes to life in the form of “the green flash,” a quick flash that appears for a nanosecond a sunset. If you want a spot even more secluded, boat over to the nearby Cayo Costa, where “deserted” is the best description of the remote, unspoiled island (which doubles as a state park). —Lane Nieset, travel writer
Population: 531
When you think of wine country and Bavarian towns, one place naturally comes to mind: the Blue Ridge Mountains. No? Well, you, my friend, have never been to Helen, the quirkiest little town in the Peach State. Turning onto the main drag is like apparating from the Deep South to the German Alps in two seconds flat. The street is lined with chocolatiers, biergartens, and souvenir shops that’ll have you thinking you’re in Europe. Outside town are a handful of wineries where visitors learn that “Georgia Wine” isn’t just a nice way of saying moonshine. It’s also set right on the Chattahoochee River, which means plenty of rafting, fishing, and hiking. If you can’t make it in the summer, Oktoberfest here is, unsurprisingly, quite the event. —MM
Population: 2,470
Your last stop before hitting the Road to Hana should be this former plantation village on the northeast coast of Maui, where laid-back locals and world-class beaches will give you all the aloha feels. Window shoppers will love strolling down the boutique-lined streets (keep an eye out for celebs like Willie Nelson and Woody Harrelson). Along the town’s north shore, aspiring surfers can hang ten at Ho’okipa Beach Park, where international windsurfers compete for world champion status. Or, maybe it’s better to let the pros do their thing while you chow down on pizza and beer at Flatbread Company—or hit up Paia Fish Market for ridiculously fresh seafood. Boogie board along the white, sandy shores of Baldwin Beach Park and stick around for the explosively colorful sunset. —Ryan MacDonald, travel writer
Population: 1,984/2,157
Affectionately dubbed “Wydaho” given its close proximity to Wyoming, the sun-drenched Teton Valley is flanked by parallel mountain ranges, the Tetons and the Big Holes, with two “downtowns”—Driggs and Victor—about 11 minutes apart. Here, cowboys and ranchers wave at each other when they pass on the road and Burger Kings close due to unpopular demand. The Grand Targhee Resort in Wyoming (which can be accessed from the Idaho side) beckons winter and summer thrill-seekers with its bike park and Nordic skiing. Hike Darby Canyon’s Wind Cave Trail or float the Teton River in a kayak and spot beavers and huge moose. Meet locals at one of several unofficial town halls, like Victor’s Wildlife Brewing, an evolved garage brewery with fringe pool tables and world-class pizza, where you’ll hear tales of East Coast refugees transforming into local ski bums. One of them owns the place. —Bruce Northam, travel writer
Population: 3,308
Drive 10 minutes east of the mighty Mississippi and you’ll tap right into the quirky small-town vibes of Galena. Once the home of Ulysses S. Grant, Galena boasts cobblestone streets and historic mansions, plus an old-school blacksmith shop and the P.T. Murphy Magic Theater. A free trolley ride will drop you downtown, where you can stroll Main Street’s restaurants, antique shops, galleries, and boutiques bursting with kitsch. If you’re feeling active, book a rafting trip, hit up the nearby ski resort, or try the 40-acre Horseshoe Mound, known for its winding bike trails and scenic views all the way to Iowa and Wisconsin. —Josh Mellin, travel writer and photographer
Population: 1,256
It’s the art, not the music, that defines Indiana’s Nashville. This tiny town near Bloomington was home to American impressionist painter T.C. Steele, who settled here in 1907. His home is a fascinating walk through his life, art studio, and wife’s well-kept garden. Be sure to visit the Brown County Art Gallery, the original artist collective where independent artists still work and sell Hoosier-made paintings (albeit for a hefty price). If you’re looking for a thrill, stay outside of town at the somewhat creepy Story Inn. One of the rooms is supposedly haunted by a ghost known as the Blue Lady. It’s also a fine place to have a beer—the bar dates back to Prohibition, and the inn sits adjacent to some of the best hiking in Brown County State Park. —Tim Ebner, food and travel writer
Population: 7,587
Next time you find yourself trying to break the ice with some statuesque Norwegian at a cocktail party, bust this one out: “You ever been to Vesterheim, the National Norwegian-American Museum? No? It’s in Decorah, Iowa, and let me tell you…” Decorah is a jumping-off point for the best wilderness in the Hawkeye State: canoeing, mountain biking, cross-country skiing, fishing, and bird-watching are a short drive out of town. You’ll also find the Toppling Goliath Brewing Co. here. Breweries nowadays are about as rare as stoplights, but this one produces Kentucky Brunch, an imperial coffee stout aged in whiskey barrels that was once named best beer in the world—and that’s saying something. —MM
This Midwest State Is So Much More than Corn, Caucuses, and Flyover Country
Population: 27,788
Dodge City once served as the setting for numerous early-1900s Western flicks, the town’s fictional calamities inspiring folks around the country to utter the cliche “let’s get the heck out of Dodge” at the first sight of trouble. Nowadays, the brouhahas have waned, but Dodge clings to its Wild West roots. Sure, you can go the modern route with blueberry sours at the region’s first downtown brewery or chicken-fried steak with roasted jalapeño gravy at Prime on the Nine, but the chance to get caught in a time warp is much more alluring. The Boot Hill Museum is a melee of Wild West artifacts, antique guns, saloons slinging sarsaparilla soda, and reenactments of cowboy shootouts, while the city’s first and only dinner theater, Depot Theater, housed in the red-brick 1898 Santa Fe Depot, puts on performances like “Steel Magnolias.” The Santa Fe Trail preserves wagon rut trails from the 200-year-old pioneer highway, and the Boot Hill Distillery pours quirky cocktails (like a pickle juice and white whiskey tipple paired with potato chips) in a neo-saloon setting, with nary a reason to get the heck out of Dodge in sight. —Matt Kirouac, food and travel writer
Population: 13,567
The so-dubbed “Bourbon Capital of the World” is not pulling punches when it comes to the brown stuff—Bardstown is home to Four Roses, Willett, Maker’s Mark, Barton 1792, the Jim Beam American Stillhouse, and the Heaven Hill Bourbon Heritage Center, as well as the oldest bar in Kentucky, Talbott Tavern. Still, you can score hooch anywhere. What sets Bardstown apart is its old-timey southern hospitality, gorgeous landscapes, and an architecturally astounding downtown that’s remained strollable and affable since 1780. And, you know, all that bourbon. —AK
Population: 2,631
Back at the turn of the 20th century, New Orleanians with a few bucks used this town just across Lake Pontchartrain as an escape from the city when yellow fever gripped the populace. After the Depression, the colorful hotels where they used to frolic fell into disrepair. In the 1970s, a group of enterprising hippies brought them back to life. Now, they’re private homes and B&Bs, lining the streets of the most hippie town on the Bayou. In addition to the cool old architecture, Abita Springs is also home to the regionally renowned Abita Brewing Company, and its “this tastes so good I should probably keep reminding myself it’s 8% ABV” Andygator pilsner. —MM
Population: 5,089
Although YA author Sarah Dessen’s books all take place in North Carolina, the little village of Bar Harbor feels cut from the same cloth. Never has a quainter New England seaside town existed, nor a better setting for a small-town coming-of-age novel. The walkable main roads are lined with ice cream parlors, mom and pop shops, twee inns, and plenty of chances to linger outside with a glass of wine (or lobster roll) in hand; head toward the water, and you’ll find seafood restaurants promising both the piping-hot chowder you came for, as well as views of sailboats and pine-covered islands on the horizon. What sets Bar Harbor apart from the rest of Maine’s charming harbor towns is its proximity to Acadia National Park, a natural haven of deep green mountains and dramatic ocean cliffs that sits less than a five-minute drive up the road. Pick blueberries (and eat blueberry pie) on the shores of Jordan Pond, lay out your towel on Sand Beach, and rise early to catch sunrise views atop Cadillac Mountain. —Tiana Attride, former Thrillist editor
The Only National Park in the Northeast Feels Like the Edge of the World
It’s a briny seaside paradise.
Population: 423
The eastern shore’s best-kept secret is this teensy, off-the-beaten-path town where one of Maryland’s biggest crabbing families—the Phillipses, of the Phillips Seafood empire—got their start in 1914. Seafood lovers should shell up here for a few days simply because it serves some of the freshest seafood in the state. Start by visiting Old Salty’s, a Maryland institution with more than a dozen crab dishes on the menu—crab pretzels, crab nuggets, soft-shell crab sandwiches, the works. Then, check out the tranquil Blackwater National Wildlife Refuge for stand-up paddleboarding, kayaking, or biking. —TE
Massachusetts: Great Barrington
Population: 7,172
Let everyone else crowd the Catskills so the largest town in the Southern Berkshires remains a secret as long as possible (except, of course, from the hikers passing through on the Appalachian Trail). History buffs will love a few fun pieces of trivia like the Main Street here was first in the country to have electric lights, Railroad Street is one of the oldest in the US, and, by the town hall, the monument that commemorates the first armed resistance against the British is on the same site as the first slave being freed. Start the morning with coffee (or a lavender latte, if you’re feeling adventurous) and a breakfast sandwich or huevos rancheros at Fuel before antique fair- and gallery-hopping around town (be sure to check Bernay Fine Art off your list). End the afternoon and ease into the evening with a drink and live music by the fireplace at aptly named The Barn. There’s also a historic inn next door, so you don’t have to go too far when you’re ready to call it a night. —LN
Population: 865
Michigan’s 3,000+ miles of coastline are home to dozens of dreamy lake towns as entrancing as they are interchangeable. And while any number of Lake Michigan towns could make this list, our heart remains in Saugatuck. An easy (and gorgeous) drive from Chicago, Indianapolis, and Detroit, Saugatuck has become an ‘Art Coast’ overflowing with galleries; a dining paradise where The Southerner and farm-to-table hotspot Pennyroyal bring James Beard cred; and an LGBTQIA+ haven full of queer-friendly resorts, bars, and even a cabaret revue. Crucially, unlike other hyped-up towns on the coast, Saugatuck has reinvented itself without losing sight of what made it lovely to begin with. Those Beard restaurants coexist with mom and pop breakfast joints. The resorts live in harmony with weatherbeaten motels and cabin rentals. And the beaches—all wind-swept white sand, dunes, lighthouses, and amber sunsets—are still sure to dazzle. —AK
Population: 19,394
Lodged in the beautiful St. Croix Valley, Stillwater is known for its gorgeous waterfront, solid hikes, and scenic spots for a summer picnic. But there’s a lot more than bluffs and hockey going down. Lift Bridge Brewery—named after Stillwater’s iconic lift bridge—is an underappreciated jewel in a state where Surly, Bauhaus, and Bent Paddle hoard the craft brew love. In the summer, Nelson’s Ice Cream and the aptly named Lumberjack Days food and music festival make the trip worthwhile. In the winter, it’s the massive Ice Castles nestled along the riverbank. And in the warmer months, you can take advantage of the fact that most restaurants downtown tout a patio with a view. —Dustin Nelson, former Thrillist writer
Mississippi: Ocean Springs
Population: 18,429
Sitting anywhere along Government Street in Ocean Springs, you can hear live music—rock, country, bluegrass, hip-hop—coming from a bar only a few feet away. The small stretch of watering holes along this coastal city’s main drag is a little slice of Austin or Nashville plopped on the Bayou, making a weekend bar crawl here as entertaining as anywhere. Your days are for paddle boarding and kayaking along the Gulf Islands National Seashore, and a short boat ride out to the barrier islands finds you on the kind of turquoise, white sand beaches you never knew existed in Mississippi. —MM
Meet the Mississippi Artist Paradise You Had No Idea Existed
A creative hub is quietly brewing on the last coast you might expect.
Population: 7,964
You can’t walk down a Boonville street without tripping over the raw Americana in the form of more than 400 registered historic sites smack-dab in the middle of Missouri. You even get slipped a dose of history reading the name, taken from founders and sons of folk hero Daniel Boone. Tour the Native American burial grounds and stay across the Missouri River at the Rivercene Mansion Bed & Breakfast, conceived as an opulent retreat for a rich riverboat captain. The outlaw Jesse James left his boot prints here, and you’re welcome to follow those as you make your way around Civil War landmarks. Want something a bit more recent but just as red, white, and blue? Pop by Warm Springs Ranch, a nearby breeding farm for the Budweiser Clydesdales. —Peter Rugg, travel writer
Population: 8,040
Livingston is the epicenter of Montana cool—a town that fully embraces its rowdy past, even as it’s become a magnet for artists and laid-back celebs like Jeff Bridges and Michael Keaton. With the iconic Murray Bar standing as the town’s main compass point, Livingston’s central location near the gates of Yellowstone and not far from more booming Bozeman allows it to thrive as an rugged outdoor paradise. Here, world-class fly fishing and rafting is as much a way of life as is sucking down whiskey shots to the soundtrack of a band playing on a flatbed truck. And if all that sounds very exhausting, the town is right next to Chico Hot Springs, which claim a century’s worth of legacy curing Murray Bar-induced hangovers.
This Rowdy Cowboy Town Is a Magnet for Artists, Celebs, and Cool Kids
This is the epicenter of Western cool.
Population: 2,633
Locals compare this region to a rainforest misplaced in the Midwest plains. It’s almost unfair to the rest of Nebraska how much of the state’s natural beauty is concentrated in this town. Six, count ’em, six ecological systems mesh together along the Niobrara River. You’ll find sandstone canyons, cliffs, valleys, and Smith Falls State Park, home to the state’s tallest waterfall. Or, run with the prairie dogs and bison in Fort Niobrara National Wildlife Refuge, or book a cabin at the Lord Ranch Resort and get the full cowboy tour package. Later, boot-scoot out of the 19th century and over to the Peppermill Restaurant, where you can get a fresh steak without looking it in the eye first. —PR
Population: 20,564
If you’re not into desert landscapes, anywhere in Nevada not called Vegas or Tahoe won’t be for you. But if you can appreciate the beauty of vast, sandy plateaus backed by majestic red mountains, Elko is the spot for you. It’s Nevada’s equivalent of a Rocky Mountain town without the tourists or the painful price tags. The annual National Cowboy Poetry Gathering convenes here, because just like those cowboy poets, beneath its rough exterior Elko has an artistic soul. The streets are lined with shops from artisans hawking crafts, paintings, photographs, and the kinds of wares one would more expect to see in a place like Aspen. It’s also a jumping-off point to the Ruby Mountains and canyons beyond, where extreme hiking, heli-skiing, and off-road ATV-ing are daily adventures.—MM
Leave Las Vegas to See the Most Beautiful Places in Nevada
Beyond the Strip, the Silver State is full of gorgeous scenery in unexpected places.
New Hampshire: Portsmouth
Population: 21,956
A stone’s throw from the Maine border, Portsmouth was founded in 1623, making it one of the oldest towns in the country. Spend a weekend on a walking tour of historic homes, taking in the waterfront, hopping a harbor cruise, and strolling Market Street—and pepper that with pit stops at the many top-notch breweries (Smuttynose and Stoneface among them). If you can, time your visit around the popular annual Chowder Festival (which should hopefully return next year!) or Prescott Park Arts Festival. Don’t leave without hitting the wonderfully retro The Friendly Toast for brunch. —Joe McGauley, former Thrillist editor
Population: 1,449
If you want to experience the Jersey Shore sans spray-tanned mooks and barrels of industrial sludge, Sea Bright is a veritable 1.2-square-mile oasis of bars you actually want to visit, beaches where you can find a nook to yourself, and everything else you love about summer—including ice cream. Surrounded by the mighty Navesink River on the west and the even mightier Atlantic on the east, Sea Bright is filled with membership-only beach clubs for the locals and a swath of public beaches for out-of-towners. Snooki would not feel at home here—SB isn’t overwhelmed by kitschy tourist traps and saltwater taffy stands. This is where people from New Jersey go when they go to the Shore. If you’re lucky, you might even spot Bruce Springsteen working on his tan (yes, seriously). —Wil Fulton, former Thrillist editor
New Mexico: Truth or Consequences
Population: 6,052
Does the very name of this town not do most of the heavy lifting, as far as piquing interest goes? But even if it wasn’t called Truth or Consequences—a moniker earned from a contest run by a 1950s game show of the same name—there’d still be plenty to draw the curious out to this particular corner of New Mexico. Back in the day, it was called Hot Springs, because—as you may be able to guess—there are healing mineral springs found all throughout the town. The best of the bunch is arguably Riverbend, where you can take a scenic soak in full view of the Rio Grande and the Caballo Mountains. When you’ve dried off, book a tour through Sierra Grande to take a bison and coyote safari or explore the bone-white dunes of White Sands National Park less than two hours down the road. (P.S. Call it T or C—you’ll sound more like a local, and it’ll save you a helluva lot of time.) —TA
Yes, Truth or Consequences, New Mexico Is a Real Place
The weirdest town name in the Southwest.
Population: 6,287
In a state that’s home to the Hamptons, Finger Lakes, Appalachian Trail, and Big Apple, it’s no surprise that small communities like Woodstock, New York, fall to the back of Empire Staters’ minds. To assume that Woodstock is only notable for its namesake 1969 music festival would be a major blunder—the festivities weren’t even held within city limits. In reality, Woodstock is a charming little Catskills oasis where residents prop up an art, religion, music, and theater scene worthy of national attention. The Woodstock Byrdcliffe Guild continues to attract artists hoping to retreat from city life and hone their craft, and visitors can tour the grounds and see where magic was made. At the Maverick, a barn-like concert hall that’s still in operation today, locals have been enjoying outdoor “hippie” music festivals since the dawn of the 20th century, and in the summer, the city hosts outdoor concerts at the Village Green for all to enjoy. When you’re ready for a dose of nature, make your way to the Overlook Mountain Wild Forest—the 4.6-mile mountain trail begins beside the monastery and runs along ruins of a never-completed hotel, a historic fire tower, and stunning viewpoints of the Hudson Valley. —Kyler Alvord, former Thrillist writer
Population: 4,464
Coastal North Carolina swarms with idyllic beach towns: Wrightsville Beach, Hatteras Island, Seaside. The best-rounded of them is Beaufort, where antebellum architecture and farmers markets under oak trees meet serene Southern coastline and vast, open prairies. Watch the sunrise over the ocean, then head out deep-sea fishing, dolphin-watching, or driving through fields full of wild horses. The wilderness here is actually wild, and while the houses along the shoreline are plentiful, nothing ever feels crowded. When you can end the day with a waterfront sunset in the same spot you watched a waterfront sunrise, it’s a pretty special place. —MM
Population: 121
One would think getting Broadway-quality performers to spend their summers in the middle of nowhere, North Dakota would be tough. But it’s barely a chore when you’re drawing them to Medora, home of the Medora Musical and gateway to Theodore Roosevelt National Park. The once-depressed cattle town was brought back to life when businessman Harold Shafer sunk millions into it, turning it into an Old West Revival that avoids being too campy. Saloons and steakhouses offer stellar food; day hikes along the Pancratz Trail, just outside the Badlands Motel, offer sweeping views; and a trip to the Burning Hills Amphitheater—a sort of Hollywood Bowl in the Badlands—is a must for musicals and steak-on-a-pitchfork dinner. The entire town obliterates expectations of what one would expect to find an hour west of Bismarck. – MK
This Tiny Western Town Goes Full Broadway in the Badlands
Spectacular views and pitchfork-fried steak are deep in the Midwest.
Population: 4,188
Somewhere between Cleveland and Akron is the sleepy town of Chagrin Falls, where the brightly colored autumn trees and snow-piled winters inspired Bill Watterson as he drew Calvin and Hobbes. It has small wonders otherwise, like the town’s actual falls beneath the historic Popcorn Shop (once a stop on the Underground Railroad). But there are legitimate claims to firsts—the original Dave’s Cosmic Subs and Jeni’s (at least outside of Columbus) are here. Besides the many surrounding walkable nature preserves, the allure mainly comes from the boutique stores (and the cramped bookstore). If you tire of small-town vibes and colonial homes, northeast Ohio’s two major metropolitan areas are just 40-minute trips away. —Leanne Butkovic, former Thrillist editor
Population: 10,749
Guthrie can be forgiven for begrudging Oklahoma City. Dubbed the state capital in 1907, its glory days were cut short when the state seal was stolen in the night like a scene from National Treasure and brought 30 miles south to OKC. Luckily, the town’s essentially been preserved so that the glory days can last forever. It abounds with brick sidewalks, Victorian architecture, antique stores, pharmacies, violin shops, and murder mystery dinners in actual haunted manors. Its frozen-in-time Americana has made it a favorite for movie studios, too, from Twister (which shot the drive-in movie scene at the Beacon Drive-In Theater) to the upcoming Reagan biopic. It may not be as au courant as OKC, but Guthrie also boasts the state’s first legal distillery, WanderFolk, hipster vibes in garage-turned-cafe Hoboken Coffee, and the Dominion House, the former Children’s Masonic Home that’s been transformed into a castle-like inn with a bistro. —MK
Population: 8,313
With much respect to the Oregon coast and high desert hamlets, no small town captures the beauty of the Pacific Northwest quite like Hood River. The town rises out of the mighty and scenic Columbia River Gorge—one of the most breathtaking natural areas in the West —and climbs steadily into the foothills of Mt. Hood. This is a kitesurfing capital thanks to the steady winds, and a gateway to endless wilderness for hiking, snowshoeing, and mountain biking. You can cruise the area’s sea of orchards, called the Fruit Loop, or just stroll by the old buildings that make up the hilly, walkable downtown. Oh, and because it’s Oregon, there’s beer, lots of beer, including heavy-hitters pFriem and Double Mountain. And here, you’re allowed to stroll the esplanade with a beer in hand, provided the wind doesn’t blow it all over your shirt. —AK
Oregon’s Best Small Town Has Mountains, Waterfalls, and Ridiculously Good Beer
Step aside, Portland!
Population: 6,807
Old brick buildings, pubs, boutiques, a dance company, painting studio, and a playhouse that puts on spectacular live productions—Ambler has the quintessential small-town Main Street, only better. The Ambler Theater, located in a Spanish Colonial-style building with a hidden gargoyle on the roof, regularly plays old movies and new indie flicks like Citizen Kane and Where the Crawdads Sing. The town’s restaurants are incredible: Forest & Main converted an old house into a microbrewery and The Lucky Well has some of the best barbecue around (I have recurring dreams about its cornbread). You’ll find a delightful community of folks who gather regularly for the summer farmers market, the summertime Ambler Arts & Music Festival, and the Dog Days of Summer (seriously, a giant dog parade). Throw in a hilariously quirky history that involves a train wreck and an asbestos empire and you’ve got yourself one heck of a town. —Erin Weaver, former Thrillist editor
Population: 25,163
Nowhere in New England compares to the Gilded Age splendor of Newport, a coastal town set upon cliffs dotted with some of the most spectacular mansions of the 19th century. The must-do activity here is, obviously, touring the Newport Mansions, but that’s far from the only draw. Newport also hosts the annual Newport Regatta, one of the biggest sailing races in America, bringing with it the best sailing parties. Held in July, the Regatta is the ideal time of year to visit, but even if you miss it there are still plenty of wide, sandy beaches to lounge on for the day, and a surprisingly good wine region just on the outskirts of town. —MM
Population: 13,607
The South Carolina Lowcountry has no shortage of coastal appeal, but some areas can get a little oversaturated. But not Beaufort, a town with all the historical allure of Charleston at a slower, easy-going pace. The beauty isn’t limited to its streets: Head out to the barrier islands, like Saint Helena, where rural simplicity, fragrant marshes, and live oaks draped in Spanish moss make for instant relaxation. Experience the Gullah culture of emancipated African-American slaves who moved to these islands centuries ago and have preserved much of their distinctive language, food, and customs. Then boat out to the isolated Daufuskie Island, a car-free escape stocked with colorful characters. —MM
Visit the Sleepy Southern Town Where ‘Forrest Gump’ Was Filmed
There’s a whole lotta southern charm around here.
Population: 12,193
Western South Dakota, with its Black Hills, Badlands, and Elk Mountains, might be the most overlooked scenery in America. The best place to take it all in is Spearfish, nestled at the mouth of Spearfish Canyon. Main Street here is classic Old West, but venturing out of town is a must, whether hiking deep into Spearfish Canyon to see some of the most staggering cliff faces in America, or to Sturgis and its famous bike rally, or the casinos in Deadwood. If you must, hit Mt. Rushmore. None of it is too far for a short day trip, which may be part of the reason the most expensive real estate in SoDak can be found in Spearfish. —MM
Why South Dakota Is the Most Underrated State in America
Population: 410
Located a mere 54 miles from trendy Nashville, Bell Buckle feels more like a trip down memory lane than I-24. You’d assume the most scenic portion of town, a welcoming row of mom and pop shops, has been untouched by time aside maybe from an eco-friendly Prius parked over the town’s literal street art—an old-timey quilt painted on the road. For dinner, twice-fried pork chops await at the Bell Buckle Cafe, followed by an evening sitting in handcrafted rockers watching trains pass and sucking down a malt from the Bluebird Antiques & Ice Cream Parlor. To catch the town in its prime, head down in June for the RC Cola-MoonPie Festival, a day of crafts, shopping, Moon Pie Olympics (it’s exactly what it sounds like), and the annual cutting of the world’s largest moon pie. —Tanner Saunders, travel writer
Population: 1,788
When modern artist Donald Judd fell in love with this desert community in the 1970s, he ended up changing it forever, transforming it into an art hub renowned for its galleries and yearly film and music festivals. Judd’s Chinati Foundation is a necessary pilgrimage for any art aficionado (the drive here is no joke), as is the overly-Instagrammed Prada Marfa (plus there are amazing restaurants right in the middle of nowhere). After the sun sets, set up a folding chair at the Marfa Lights Viewing Area and watch for flashes (extraterrestrials, maybe?) dancing in the Texas sky. Enjoy a heavy pour of cheap whiskey at Lost Horse Saloon, then lay your head down in a yurt at the oh-so-trendy El Cosmico. —Kelli McDonald, marketing manager
Population: 5,366
Utah has a knack for delivering beautiful sights. Once upon a time, dinosaurs roamed and Indigenous groups inscribed petroglyphs on the land here (both of which you can still find evidence of today in Bull and Horseshoe Canyons). Now, the area is now home to Moab, a mountain town that balances rugged outdoorsy adventure with modern amenities. The gateway to the wildly popular Arches National Park and its underrated neighbor, Canyonlands, the streets often teem with tourists who are hungry—both for R&R after days spent hiking, rock climbing, and white water rafting, and in the general sense of the word. For a small, laid-back town, Moab has a surprising abundance of good eats, including Sabuki Sushi, Spitfire Smokehouse, Josie Wyatt’s Grille, Sunset Grill, and Moab Brewery, plus boutique shops like Moab Made for art and jewelry and Tumbleweed for pottery. Altogether, it’s a high desert oasis with plenty to explore indoors and out. —MK
Population: 3,005
Imagine the fictional Stars Hollow, but instead of an inn, Lorelai Gilmore runs an upscale dairy farm-turned-museum that dates back to the mid-19th century. This is Woodstock, a lovely oasis at the foot of the Green Mountains that is so picture-perfect, the town buried its telephone wires to attract more Hollywood productions (you might recognize locations around town from Forrest Gump). Take your obligatory snapshots at one of the city’s historic covered bridges, eat fresh pie at the Woodstock Farmers Market, and visit the historic Marsh-Billings-Rockefeller Mansion. Then meander to one of the other adorable towns in the Upper Valley—Barnard boasts a general store dating to 1832 and a fun summer farmers market with live music every Thursday night. —TS
Population: 302
In the foothills of the Shenandoahs, no-stoplights Sperryville is as steeped in old-time Americana as they come. Plan to stay at Hopkins Ordinary, a B&B with an onsite brewery—one of several sources of top-notch brews. Pen Druid is a wild new fermentation brewery famous for Golden Swan, made from wild yeast strains found in Sperryville’s wildflowers. Locals snag farm-fresh sandwiches at Before & After, but just up the road in Washington is The Inn at Little Washington, the first and only three Michelin-starred eatery in DC. Diners book months in advance, and diners come from near and far to try chef Patrick O’Connell’s menu. Just make sure to get to bed early—Old Rag Mountain beckons. This 9-mile hike shows off spectacular views, especially at sunrise, when you’ll find few other hikers on the trail. —TE
Small towns hardly get more picturesque than Lake Chelan. | Lake Chelan
Population: 4,237
Describing Lake Chelan is like playing Jenga with descriptors. Its crystalline namesake runs 1,500 feet deep and cuts a jagged 50-mile path perfect for parasailing, boating, or simply admiring while sipping wine. Along with being Washington’s best lake town and one of its best mountain towns, it’s also the state’s coolest wine town, with more than 30 tasting rooms showcasing a taste of the unique mountain terroir. Here, the Cascades cast a shadow over a picturesque Pacific Northwest downtown whose mom and pop restaurants include the relatively upscale Campbell’s (hope for Dungeness crab, but always bet on the local oysters) and the ultra-chill Local Myth Pizza, which does wonderful things with pizza dough and housemade chorizo. It’s a winter sports paradise, a fall color explosion, a springtime wonderland, and a summer getaway. We can keep going, but at some point, this tower of superlatives is bound to topple. —AK
Washington State’s Best-Kept Secret Is A Sun-Soaked Lake Paradise
Clear skies, great wine, can’t lose.
West Virginia: Fayetteville
Population: 2,887
Located just outside the New River Gorge, Fayetteville completely bulldozes all preconceived notions of West Virginia living—unless your preconceived notions paint it as an outdoor destination with artsy vibes and great food. Fayetteville’s rock climbing and mountain biking are unmatched, and it offers up some of the best rafting in the east. The creative spirit that its nature-loving citizens have instilled in the place gives it a homey vibe, one where Ridge Brewing fills grateful growlers and Secret Sandwich Society feeds happy masses. Things get a little livelier during Bridge Day—the state’s largest single-day festival—when hundreds of BASE jumpers leap off the New River Gorge Bridge while nearly 80,000 people gawk. But, outside of that, this is a place to quietly embrace and tempt nature. —AK
Population: 1,148
Door County is Wisconsin’s “up north” playground, a veritable show-stopping destination complete with small-town charm, miles of dramatic coastline, and quirky local businesses. The waterfront Dörr Hotel adds Scandinavian-style flair to this cozy lakeside enclave, while stalwarts like Earl’s Sister Bay Bowl & Supper Club harken back to a simpler time. Stop into Door County Creamery for the area’s best goat cheese (a strong statement in the state where dairy reigns supreme). If time allows, do the farm tour to taste cheese with a certified Master of Cheese while goats scamper about the pastoral backdrop. And speaking of goats, don’t miss Al Johnson’s Swedish Restaurant & Butik, which features a grass roof complete with the happily grazing creatures on top. If you start itching for more isolated surroundings, wind up the coast and take the car ferry across Death’s Door to Washington Island and its famed Provence-style lavender farm. —Katy Spratte Joyce, travel writer
Population: 283
This tiny outpost features all the best things about Wyoming: friendly bars, wide-open spaces, great music, and access to some of the most strikingly beautiful outdoor recreation you’ll find. Located 8,000 feet up and 30 miles outside of Laramie, at the foot of the Medicine Bow Mountain Range, Centennial consists mainly of a couple hotels and bars/music venues that play host to hikers, campers, skiers, and snowmobilers on their way into or out of the mountains. On any given weekend, the town is liable to turn into a party (especially when the right bands are passing through). It’s also the home of the greatest winter party you’ll ever find—the annual Poker Run, where a few hundred well-lubricated skiers tumble down the mountain and crash-land in Centennial’s welcoming arms.—Bison Messink, former Thrillist editor
Saddle Up in This Western Mountain Town You’re Missing Out On
Giddy up in the mountains, drink beer in town.
Want more Thrillist? Follow us on Instagram, TikTok, Twitter, Facebook, Pinterest, and YouTube.
