Coolest Small City in Every State

Coolest Small City in Every State

BY Matt Meltzer | September 23, 2023

When we think about traveling around the United States, two things generally come to mind. First and foremost are the big cities filled with fantastic food, creative music and just about every kind of weirdo you can think of. Then, there’s the wide open spaces, the beautiful part of “America the beautiful,” like national parks and wild shorelines. Lost somewhere in between are the smaller cities, often overlooked places that operate at a slower pace and a smaller scale, but still pack in plenty of great food and outdoor beauty of their own. Many have a fascinating history too; old buildings and creaky bed and breakfasts take you to a different time and place. Every state has at least one of these less-heralded cultural centers. Here’s a look at the coolest small city in every state.

Orange Beach, Alabama
#1
Perdido Pass, Orange Beach, Alabama. Photo via Shutterstock.

Orange Beach, Alabama

Orange Beach, Alabama, USA

Outside the south, few people know Alabama has a stretch of Gulf Coast beaches that rival anything across the border in Florida. The epicenter of it all is Orange Beach, a highrise-filled strip of white-powdered sand that’s home to the “Bama” side of the famous Flora-Bama roadhouse. You can sweat out all those bushwhackers (a Flora-Bama boozed up milkshake) by renting a bike and exploring the over 28 miles of bike trails inside Gulf State Park, or relaxing at the oceanside restaurant at the park’s luxe lodge. Orange Beach is also the low key home of some of southern Alabama’s best restaurants like Fisher’s Upstairs and Doc’s Seafood Shack. A little west, you can  grab a burger at the legendary Pink Pony in Gulf Shores.

Do you recommend this?

+29
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Rating: +28. From 30 votes.
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#2
Downtown of Sitka, Alaska, at sunset. Photo via Shutterstock.

Sitka, Alaska

Sitka, Alaska, USA

By land mass, Sitka isn’t small at all. In fact, it’s the largest city in the United States in terms of physical size, clocking in at over 2,800 square miles. With that much space, the city has an abundance of outdoor recreation: you can hike to the top of Harbor Mountain for some spectacular views of the Alaska wilderness or stare into the caldera of a volcano at the end of a 10-mile hike to Mt. Edgecumbe. In town, you can get familiar with some native birds at the Alaska Raptor Center or paddle around Alaska’s coastal islands on a kayak. The seafood in Sitka is all you’d expect in coastal Alaska, best experienced by taking a tour with Taste of Sitka.

Do you recommend this?

+20
0
Rating: +20. From 20 votes.
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Sedona, Arizona. Photo via Shutterstock.
#3
Sedona, Arizona. Photo via Shutterstock.

Sedona, Arizona

Sedona, Arizona, USA

Sedona is, according to pretty much everyone who lives and visits there, an energy vortex. That doesn’t mean you’re getting sucked into some kind of parallel universe if you wander into the wrong red rock cave, but it does mean the city has a certain spiritual energy that draws, well, the kind of people who travel for spiritual energy. If you’re not into psychics and sweat lodges, Sedona is still pretty cool, as the city is surrounded by desert mountains and  iconic hikes like the Devil’s Bridge and Cathedral Rock trails. Sedona can claim some fantastic southwestern food, too. Go high end dining at Cress on Oak Creek, or keep it casual at Cowboy Club and Grille.

Do you recommend this?

+27
-4
Rating: +23. From 31 votes.
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Eureka Springs, Arkansas, USA - July 5, 2021: Historic downtown Eureka Springs, AR, with boutique shops and famous buildings. Photo via Shutterstock.
#4
Eureka Springs, Arkansas, USA - July 5, 2021: Historic downtown Eureka Springs, AR, with boutique shops and famous buildings. Photo via Shutterstock.

Eureka Springs, Arkansas

Eureka Springs, Arkansas, USA

Arkansas isn’t the first place you would expect to find a hippie commune or nudist Airbnb, but that’s the charm of this quirky little enclave in the Ozarks. The town is named for the city’s water springs which are said to have healing powers and, in the 1800s, sparked tall tales of local miracles that spread across the country. It’s still a place for religious pilgrimage, with a 66-foot statue of Jesus Christ sitting atop a hill drawing dozens of visitors daily. In town, the Victorian-style architecture makes even a short stroll a treasure trove of photo ops. For a little morbid history, stay at the Crescent Hotel and Spa, a haunted inn once run by a crooked doctor who didn’t report patient deaths and continued collecting money from their families.

Do you recommend this?

+22
0
Rating: +22. From 22 votes.
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Carmel by the Sea, California
#5
Carmel, United States - November 19 2011 : shopping on main street of Carmel with luxurious expensive boutiques all around. Photo via Shutterstock.

Carmel by the Sea, California

Carmel-by-the-Sea, California, USA

California is a state overflowing with cool locales, but it’s pretty tough to beat a town that once had Clint Eastwood as its mayor. Carmel by the Sea is a maze of cottage style architecture that feels like a European village set on the California Coast. It’s an upscale destination to be sure, home to Michelin-starred Aubergine and Chez Noir, which share the city with chic celebrity hangouts  Terry’s Lounge and the Hog’s Breath Inn. The reason the town draws such well-heeled crowds is the access to the ocean. You can go whale watching pretty much all year long or just explore the tide pools and beaches at Point Lobos State Nature Reserve.

Do you recommend this?

+36
-8
Rating: +28. From 44 votes.
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Telluride, Colorado
#6
Downtown Telluride, Colorado, in the spring. Photo via Shutterstock.

Telluride, Colorado

Telluride, Colorado, USA

Far from the confluence of upscale resort cities further north, this former mining town in southwestern Colorado retains its rustic draw by being so darned hard to get to. Yes, you can find commercial flights to Telluride, but typically getting here involves driving a few hours through national forests and conservation areas, until finally you roll onto one of the most photographed Main Streets in the country. Once you’re in Telluride, you’ll be treated to some of the best skiing in the state during the winter, and easy access to hikes to the top of 14-ers in the summer. The city has gained acclaim for Jimmy Buffett’s Blues and Brews festival as well as a celeb-strewn film fest on Labor Day weekend. You can get a taste of the Old West at the fabled Silver Dollar Saloon, where parties run late, or enjoy drinks with a view of the town at the bar atop the New Sheridan Hotel.

Do you recommend this?

+28
-5
Rating: +23. From 33 votes.
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Mystic, Connecticut
#7
Lobster traps on dock at Mystic Seaport, Mystic, Conn. Photo via Shutterstock.

Mystic, Connecticut

Mystic, Stonington, Connecticut, USA

This coastal Connecticut town became famous because of the 1988 film Mystic Pizza, but its maritime heritage is the reason vacationers flocked here for years before the movie. It’s a perfect glimpse of oceanside New England. You can rent boats or paddleboards and float past stately old homes, then delve into the undersea world at the Mystic Aquarium or Seaport Museum. The A-frame architecture gives you  the quintessential northern nautical experience, and salty (in a good way!) locals fill the bars and restaurants.

Do you recommend this?

+24
-3
Rating: +21. From 27 votes.
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Bethany Beach, Delaware. Photo via Shutterstock.
#8
Bethany Beach, Delaware. Photo via Shutterstock.

Bethany Beach, Delaware

Bethany Beach, Delaware, USA

Though we give a hearty tip of the hat to Rehoboth Beach, Bethany Beach has all the same mid-Atlantic coastal draw with a far more relaxed vibe. You can still stroll the boardwalk here, taking pictures along its half mile of whitewashed buildings and landmark clock. And while it’s not exactly empty in the summer, the crowds are thinner and the energy calmer, allowing you to unwind a little more. Popular restaurants like 14 Global, Pie and Blue Coast serve  fantastic seafood that’s a cut above standard beach fare. For something even more peaceful, meander through Delaware Seashore State Park and see the coastline as it was before the developers moved in.

Do you recommend this?

+24
-1
Rating: +23. From 25 votes.
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St. Augustine, Florida. Photo via Shutterstock.
#9
St. Augustine, Florida. Photo via Shutterstock.

St. Augustine, Florida

St. Augustine, Florida, USA

Anyone who’s played a game of Trivial Pursuit knows St. Augustine is the oldest established city in America, but few outside the Sunshine State know what a gem of history, food and nature it is. Take a tour of the old city, or a ghost tour if you dare, and wander past the city’s first schoolhouse, haunted bars and the Spanish fort Castillo de San Marcos. Scarlett O’Hara’s sadly closed in 2022, but you can still get your ghosts-and-gimlets fix at Stogie’s, where spirits of ill-fated poker players still play tricks in the bathroom.  Head just outside the old city to the St. Augustine Alligator Farm and navigate a ropes course that ziplines over pits of hungry alligators. A trip across the Intracoastal brings you to some of the more secluded beaches in Florida; if you drive a little north to Ponte Vedra, you’ll find Guana River State Preserve, a golden-duned beach that feels more like Zanzibar.

Do you recommend this?

+38
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Rating: +37. From 39 votes.
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Helen, Georgia
#10
Helen, Georgia. Photo via Shutterstock.

Helen, Georgia

Helen, Georgia, USA

As you careen through Georgia’s Blue Ridge Mountains and turn north on Highway 75, you’re suddenly thrust from North America square into the heart of Bavaria. That’s the very intentional effect of Helen, Georgia, a German theme town filled with biergartens, chocolate shops, and plenty of schnitzel. Kitchy? Sure, so are most theme towns, but in Helen you can also skip right outside of town to a handful of wineries to see how the Peach State does grapes. Or make your way down yonder to the Chattahoochee River, where whitewater rafting and fishing await.

Do you recommend this?

+24
-7
Rating: +17. From 31 votes.
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Koloa, Hawaii
#11
Old and abandoned rusting truck used for sugar cane to Koloa sugar mill on Hawaiian island of Kauai. Photo via Shutterstock.

Koloa, Hawaii

Koloa, Hawaii, USA

Travel the coastal drives of any Hawaiian island and you’re sure to run into cool little surf towns. Old Koloa Town, however, has something a little different from the rest. With the state’s first sugar plantation, Koloa gives you the odd look into the early days of European Hawaii settlement. Buildings lining Old Koloa Town are a tropical take on the Old West; coffee roasters, souvenir shops and art galleries fill spaces that were once general stores and post offices. You’ll learn the history of the sugar industry on the islands as you walk along elevated wooden sidewalks with emerald green mountains towering behind you — a dramatic reminder that, despite its 19th-century facades, Koloa is in the heart of paradise.

Do you recommend this?

+11
-2
Rating: +9. From 13 votes.
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Sandpoint, Idaho
#12
Sandpoint, Idaho - July 23 2022: Tourists and local Idahoans enjoy a sunny summer day at the crowded city beach in downtown Sandpoint, Idaho. Photo via Shutterstock.

Sandpoint, Idaho

Sandpoint, Idaho, USA

Apologies to all the longtime Sandpointers who’ve seen their onetime hidden gem exposed to throngs of transplants over the past few years — that’s what you get when your little town on the shores of Lake Pend Oreille provides so much in such a small area. Schweitzer Mountain Resort was Sandpoint’s big draw for decades, but the city has forged an identity of its own through a Jack Nickalus-designed golf course, craft breweries, and the Silverwood Theme Park and Boulder Beach Waterpark. There’s also a city beach with volleyball nets and tennis courts, where you can get your tan on with unfettered views of the mountains. Check out the Clark Fork River for whitewater rafting, which you’ll find far less logjammed than the Snake or Salmon Rivers.

Do you recommend this?

+14
-13
Rating: +1. From 27 votes.
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Galena, Illinois.
#13
Galena, Illinois - October 9, 2022: View of Main Street in historical downtown area of Galena. Photo via Shutterstock.

Galena, Illinois

Galena, Illinois, USA

Tucked in the far northwest corner of Illinois, about three hours from Chicago, you’ll find this cobblestone slice of old midwestern charm. No one is confusing Galena for an action-packed metropolis, but if you want to tour old, opulent mansions and stroll main streets that look ripped from a history book, nowhere in Illinois comes close. You can waste away your days learning trades at a blacksmith shop or just stroll the art galleries and interesting boutiques downtown. Pancake-flat Illinois isn’t typically known for its scenic vistas, but venture to the top of Horseshoe Mound and you’ll find the best viewpoints in the state that don’t involve buying a ticket to the Skydeck.

Do you recommend this?

+14
0
Rating: +14. From 14 votes.
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Madison, Indiana
#14
Madison, Indiana. Photo via Shutterstock.

Madison, Indiana

Madison, Indiana, USA

Here’s a fun fact to bust out at your next cocktail party: Where is the longest contiguous National Historic Landmark in the United States? If you guessed Madison, Indiana, you’re really good with context clues. This town along the Ohio River is essentially one giant historic district, packed with Federal, Greek Revival and Second Empire architecture. It’s a popular stop with river boat cruises, as the easy downtown makes perusing the wineries, bars and restaurants easy during a short port call. If you’re looking for a little adrenaline, Madison is also home to the only New Zealand jetboat in the Midwest, and while you won’t exactly be speeding through the whitewater of Queenstown, a ride is still a hair-raising good time.

Do you recommend this?

+14
-3
Rating: +11. From 17 votes.
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Carnegie Hall on the campus of Grinnell College. Photo via Shutterstock.
#15
Carnegie Hall on the campus of Grinnell College in Iowa. Photo via Shutterstock.

Grinnell, Iowa

Grinnell, Iowa, USA

Basketball geeks may recognize this name from the Grinnell System- a run-and-gun, what-the-heck-is-defense style of hoops developed by fabled coach David Arsenault. It originated at the namesake college in this little Iowa town where games are still free to attend and scoring is still off the charts. Roundball isn’t why this town is so cool, though it does make for an interesting footnote. It’s more that the city combines midwestern ethos with college town progressiveness. You can post up at a diner or sip chardonnay in a wine bar, and the crowds will look pretty much the same. The walkable downtown is anchored by the Louis Sullivan Jewel Box Bank, a national historic landmark designed by the “father of the skyscraper” that’s now Grinnell’s visitor’s center. You can also stay at the Hotel Grinnell, a converted junior high with chalkboards in the rooms and a restaurant  called The Periodic Table.

Do you recommend this?

+8
-4
Rating: +4. From 12 votes.
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Humboldt, Kansas. Photo via Shutterstock.
#16
Humboldt, Kansas. Photo via Shutterstock.

Humboldt, Kansas

Humboldt, Kansas, USA

How, exactly, did a Kansas town of just over 1,800 land itself on the The New York Times vaunted list of 52 places to visit? Well, it starts with a group of local business leaders who made a concerted effort to revitalize this sleepy rural town. The rebirth began with Base Camp, a full-service campground with instant access to the Prairie Spirit Trail. Closer to downtown, Humboldt has seen an explosion of big city style restaurants highlighted by Honeybee Bruncherie and its Insta-famous interior. What’s more, it’s gained acclaim for Bijou Confectionary, a home-town modern candy shop which may remind some of a smaller, subtler Dylan’s.

Do you recommend this?

+9
0
Rating: +9. From 9 votes.
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Bardstown, Kentucky. Photo via Shutterstock.
#17
A statue of songwriter and composer Stephen Foster sits in My Ol' Kentucky Home State Park, the site that inspired the famous song, in Bardstown, Kentucky. Photo via Shutterstock.

Bardstown, Kentucky

Bardstown, Kentucky, USA

Bardstown bills itself as the bourbon capital of the world, and after a few days there it’s hard to argue. The home of Maker’s Mark, the Jim Beam American Stillhouse and its namesake Bardstown Bourbon Company, this small city is a whiskey lover’s dream, with some of the best spirits in the world  within the same few miles. The town has more than just distillery tours, however.  A walk down its old southern main drag along Highway 150 brings you past interesting little restaurants like Kreso’s and Café Primo before arriving at Volstead Bourbon Lounge and its almost overwhelming selection of whiskey.

Do you recommend this?

+16
-2
Rating: +14. From 18 votes.
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Slidell, Louisiana. Photo via Shutterstock.
#18
Slidell, Louisiana. Photo via Shutterstock.

Slidell, Louisiana

Slidell, Louisiana, USA

Set along the north shore of Lake Pontchartrain, Slidell is less than 45 minutes from the French Quarter but feels a world away. It possesses one of the state’s largest antiques districts, which twice a year holds a destination antique fair that draws thousands. Downtown Slidell also recently opened a new art installation, suspending 80 colorful umbrellas over the antique shops of First Street. Beyond home design, Slidell gives you instant access to the Louisiana bayou and the animals that call it home. Jump on a Honey Island swamp tour and you’ll find yourself surrounded by dripping Spanish moss in a swamp of alligators and raccoons.

Do you recommend this?

+14
-11
Rating: +3. From 25 votes.
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Bar Harbor, Maine. Photo via Shutterstock.
#19
Bar Harbor, Maine. Photo via Shutterstock.

Bar Harbor, Maine

Bar Harbor, Maine, USA

The gateway to Acadia National Park is awash in Down East allure a seaside haven that could just as easily be mistaken for Jessica Fletcher’s fictional Cabot Cove. Bar Harbor takes on different personalities depending on which season you visit. Summer brings a slew of seasonal residents filling up its fresh seafood joints, ice cream shops and little family-run stores. In fall and spring, you’ll find year-rounders tending to their boats and heading out on sailing adventures, and tourists looking to hit the park during shoulder season. Winter is, well, winter in Maine, but if you’re up for cold weather fun, the snowmobile trails around town are some of the best around.

Do you recommend this?

+44
0
Rating: +44. From 44 votes.
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Frostburg, Maryland
#20
Frostburg, Maryland

Frostburg, Maryland

Frostburg, Maryland, USA

Journey to the far western side of the state and into the Allegheny mountains and you’ll find this jumping off point of the Great Allegheny Passage. The brick-lined streets of downtown lead to a trailhead that’ll take you through the hills to Pittsburgh in one direction and Cumberland in the other, attracting outdoors and mountain types year round. You can also hop on the Western Maryland Scenic Railroad if you’d rather take in the sites in air-conditioned comfort, drink in hand. Pop into classic small-town eateries like Clatter Café, the Princess Restaurant or Donut and Go to try some surprisingly satisfying eastern mountain cuisine.

Do you recommend this?

+85
-13
Rating: +72. From 98 votes.
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Stockbridge, Massachusetts.
#21
Stockbridge, Massachusetts. Photo via Shutterstock.

Stockbridge, Massachusetts

Stockbridge, Massachusetts, USA

The Berkshires are the kind of place you drive through, look at whoever you’re with, and say, “Boy, this looks like a Norman Rockwell painting.” The reason for that is because much of Rockwell’s work was inspired by Stockbridge and its surroundings, so much so the town is home of the Norman Rockwell Museum. His images of pastoral American life aren’t the only cultural attraction:  Stockbridge is also home to the Clark Art Institute and a large collection of historic homes and museums. In the winter, Main Street turns into a Christmas wonderland, another classic image of Americana you can only find in Stockbridge.

Do you recommend this?

+18
-5
Rating: +13. From 23 votes.
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Traverse City, Michigan
#22
Downtown Traverse City, Michigan. Photo via Shutterstock.

Traverse City, Michigan

Traverse City, Michigan, USA

When one thinks of wine along the  45th parallel, places like the Piedmont region of Italy and France’s Loire Valley come to mind. And, of course, northwest Michigan. The Leelanau Peninsula is one of the most underrated wine regions in the world, and its trail of 40 wineries sits just outside Traverse City. This town of nearly 16,000 is also a gateway to untamed Michigan nature like the Sleeping Bear Dunes National Lakeshore, and just welcomed a brand new boutique hotel at the Alexandra Inn. It’s an ideal spot for early-season leaf peeping too, though if you go a little later you can hit ski season at the Crystal Mountain Resort. And if the wineries aren’t boozy enough for you, the Traverse City Whiskey Company just opened a 70,000 square foot facility following a $20 million investment.

Do you recommend this?

+24
-3
Rating: +21. From 27 votes.
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Grand Marais, Minnesota
#23
U.S. Coast Guard Station of North Superior at Grand Marais, Minnesota on Lake Superior. Photo by Shutterstock.

Grand Marais, Minnesota

Grand Marais, Minnesota, USA

If you find yourself traversing one of the most scenic roads in the United States, Minnesota’s North Shore Dive, a stop in Grand Marais is a must. This town about 40 miles from the Canadian border is a quick peek into rugged northern life along the great lakes: Scandinavian heritage runs deep and locals are as hearty as they are friendly. Sven and Ole’s is the move for lunch along the way, plating some of Minnesota’s best pizza a block or so from the bay. It’s one of several funky eateries in the few square blocks of downtown, outfitted with ice cream, donuts and even an Indian food truck. No stop in Grand Marais is complete without sampling a few selections at Voyageur Brewing, a Minnesota staple that got its start right along the lake shore.

Do you recommend this?

+10
-2
Rating: +8. From 12 votes.
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Ocean Springs, Mississippi
#24
Ocean Springs, Mississippi. Photo via Shutterstock.

Ocean Springs, Mississippi

Ocean Springs, Mississippi, USA

This artsy village just east of Biloxi is often thought of as a beach destination. While its little spit of powdery white sand is lovely, that’s not why Ocean Springs is so cool. Creativity is everywhere in Ocean Springs, from the abundance of art and live music, to the floating cabins at the Beatnik Hotel, the breakfast biscuits at the Greenhouse on Porter and the inventive food at Vestige. You can bar hop in the open container district along Government Street and see five different live bands in a night. The next day, push through your hangover and hit the Walter Anderson Museum of Art to learn all about Ocean Springs’ favorite son and the artists he brought here.

Do you recommend this?

+27
-2
Rating: +25. From 29 votes.
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Branson, Missouri
#25
Branson, Missouri. Photo via Shutterstock.

Branson, Missouri

Branson, Missouri, USA

Beyond its regional fans, not many people know about Missouri’s theme park and rollercoaster dreamland set smack in the middle of the Ozarks. Which is surprising because Branson has no shortage of thrills. Mountain coasters, giant slingshots and live music revues wind through the hillsides. Silver Dollar City, an old-west theme park, is brimming with high speed coasters that have become destinations unto themselves. And things only get wilder off the tracks. For example, the Titanic Museum, a full-scale mockup of the famous sunken luxury liner.

Do you recommend this?

+22
-12
Rating: +10. From 34 votes.
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Livingston, Montana
#26
Livingston, Montana - July 3, 2021: View of the downtown area of Livingston, the gateway to Yellowstone National Park. Photo via Shutterstock.

Livingston, Montana

Livingston, Montana, USA

Few Montana cities have embraced their influx of transplants quite as well as Livingston. Cowboys and creative types live side by side without sacrificing any of the town’s western grit. Downtown is still filled with neon-signed country bars with dead animal heads on the wall, but walk inside any honky tonk and you’ll find live bands and crowds hailing from all over. Livingston was born as a gateway to Yellowstone, and there’s fantastic flyfishing on the river as well as year-round access to the park less than an hour away. The lower cost of living and wide open spaces have drawn accomplished chefs, whose creations you can try at restaurants like 2nd Street Bistro and Campione.

Do you recommend this?

+21
-1
Rating: +20. From 22 votes.
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McCook, Nebraska.
#27
McCook, Nebraska, in a veil of rain. Photo via Shutterstock.

McCook, Nebraska

McCook, Nebraska, USA

McCook is the rough midpoint between Denver and Omaha. Today that doesn’t mean much, but in the stagecoach and train era, McCook’s position made it an oasis of civilization in the vast western prairies. McCook remains a bastion of culture in the country’s middle, welcoming a brand new downtown arts district in 2023 to go along with its annual storytelling and music festivals. McCook has its own  James Beard Award winning bakery, Sehnert’s, and Nebraska’s only Frank Lloyd Wright-designed house, which once belonged to the inventor or Kool-Aid. All walls are still intact.

Do you recommend this?

+11
0
Rating: +11. From 11 votes.
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Virginia City, Nevada.
#28
Virginia City, Nevada. Photo via Shutterstock.

Virginia City, Nevada

Virginia City, Nevada, USA

The American West, and Nevada in particular, aren’t lacking for old mining towns. But scarcely any do as much with their old west heritage as Virginia City. The historic buildings here have been immaculately preserved, the best example being the iconic Piper’s Opera House, which still hosts live performances. Virginia City isn’t satisfied existing as a simple time warp, instead forging its 21st Century identity as a home for quirky competitions. The annual World Championship Outhouse Races are perhaps the most notorious, pitting creative porta-john decorators against each other as they race their creations through downtown. Come in September for the International Camel and Ostrich Races, which draw bigger crowds than some professional sports teams.

Do you recommend this?

+15
-5
Rating: +10. From 20 votes.
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Lincoln, New Hampshire.
#29
Lincoln, New Hampshire. Photo via Shutterstock.

Lincoln, New Hampshire

Lincoln, New Hampshire, USA

Skiing along the “ice coast” isn’t quite like cruising the powder in Utah, but if you’re in New England and want to hit the slopes you’d be hard pressed to do better than Lincoln. The town of 1,600 is home to the Loon Mountain Resort which possesses plenty of narrow, high-speed runs to hone your edge-cutting turns. The resort has its own onsite winery, so you can reward yourself for a long day of skiing with a glass of small-production wine. Moreover, Lincoln  is a great home base for exploring Franconia Notch State Park during the summer. The park has some of the best hiking and mountain biking in the state.

Do you recommend this?

+12
-2
Rating: +10. From 14 votes.
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Asbury Park, New Jersey
#30
Asbury Park, New Jersey. Photo via Shutterstock.

Asbury Park, New Jersey

Asbury Park, New Jersey, USA

Any number of small towns along the Jersey Shore could make a case for being the Garden State’s coolest. And while roller coasters and Victorian houses are neat, none of them can touch the Stone Pony, the club where Bruce Springsteen, Jon Bon Jovi and other Jersey legends got their start. Asbury Park has also upped its luxury travel game in recent years, helped by a large-scale revitalization of the city’s boardwalk. The Asbury Ocean Club brought the city its first five-star boutique hotel in 2019, to go along with the Asbury Hotel and its Victorian-meets-rock-and-roll motif.

Do you recommend this?

+19
-7
Rating: +12. From 26 votes.
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Chimayo, New Mexico
#31
Chimayo, New Mexico - June 19, 2019: Shop Art Gallery souvenir store in small town New Mexico city village with adobe style architecture on high road to Taos. Photo via Shutterstock.

Chimayo, New Mexico

Chimayo, New Mexico, USA

For Catholics, no site in the American southwest is as important as El Santuario de Chimayo, an adobe church that dates back to the early 1800s. The church receives over 300,000 visitors a year, and even if you’re not religious, the architecture and ornate design is worth the day trip from Santa Fe. The town itself is populated by famous weaving families who make crafts that will become conversation pieces when you bring them home. Top off the experience with a meal at the adobe-style hotel Rancho de Chimayo, where traditional New Mexican cuisine is served under the desert sky.

Do you recommend this?

+16
-4
Rating: +12. From 20 votes.
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Cooperstown, New York
#32
Cooperstown, New York - June 21, 2021: The Sandlot Kid statue at the entrance to Doubleday Field. Photo via Shutterstock.

Cooperstown, New York

Cooperstown, New York, USA

Baseball fans know Cooperstown as home to the National Baseball Hall of Fame. If you’ve ever been, you know it’s the hall by which all others are to be judged. The building itself sits in the center of a charming, Anytown USA downtown, except instead of hardware stores and souvenir shops, everything in Cooperstown is all about baseball. The little city nestled on the shores of Otsego Lake in the Catskills is also unfairly scenic. Even if you’re not into baseball, a waterfront meal at the Otesaga Resort will feel like a treat. The craft beer crowd may recognize local brewer Ommegang, whose taproom is less than 10 minutes from downtown.

Do you recommend this?

+26
-4
Rating: +22. From 30 votes.
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Boone, North Carolina
#33
Boone, North Carolina. Photo via Shutterstock.

Boone, North Carolina

Boone, North Carolina, USA

The home of Appalachian State University, Boone has emerged as a less-hectic mountain destination than some of its more popular North Carolina neighbors. The city has a strong college town vibe, and students frequent the funky taquerias and diners in town as well as the hikes to Blowing Rock outside the city. While the historic streets of downtown are homey, Boone’s cool stems from its outdoor recreation. In addition to Blowing Rock, you can visit the biosphere reserve at Grandfather Mountain or see the high country sites by rail on the Tweetsie Railroad. Boone has a handful of scenic hillside wineries around town too, easily navigable along this helpful wine trail.

Do you recommend this?

+30
-2
Rating: +28. From 32 votes.
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Medora, North Dakota
#34
Medora, North Dakota: November 21, 2021: United States Post Office in Medora, North Dakota. Photo via Shutterstock.

Medora, North Dakota

Medora, North Dakota, USA

Set among the Burning Hills outside Theodore Roosevelt National Park, Medora is a former cattle town that reinvented itself thanks to a large investment from Mr. Bubble inventor Harold Shafer. His Medora Foundation restored the historic western downtown, and renovated the Burning Hills Amphitheater into one of the coolest music venues in the country. Take a trip in the summer and stay in town, explore the park, then take in the Medora Musical. It’s an all-American revue with a backdrop of the North Dakota badlands. A Hollywood-like mountain sign reading “Medora” is frequently scaled by elk and deer during the performance.

Do you recommend this?

+9
-2
Rating: +7. From 11 votes.
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Put In Bay, Ohio.
#35
Put In Bay, Ohio. Photo via Shutterstock.

Put In Bay, Ohio

Put-in-Bay, Ohio, USA

Put In Bay is a little island in Lake Erie that’s been called The Key West of the North. Travel here in the summer and you’ll understand why, as raging pool parties at hotels throughout the island make it feel like a sloppy sophomore year spring break for three straight months. That’s not to say Put In Bay is only for people who enjoy Jager shots for breakfast. It’s also got the Crystal Caves as well, an underground cavern with the world’s largest geode and an onsite winery. When it’s not going full tilt, downtown Put In Bay is a fun, walkable area filled with outdoor restaurants and souvenir shops. Just don’t expect an in-season trip here to be anything resembling peaceful.

Do you recommend this?

+11
-1
Rating: +10. From 12 votes.
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Medicine Park, Oklahoma
#36
Medicine Park, Oklahoma. Photo via Shutterstock.

Medicine Park, Oklahoma

Medicine Park, Oklahoma, USA

Cobblestone towns run aplenty in the Old World, but in the United States they aren’t quite so common. That’s what makes Medicine Park in southwest Oklahoma  special: the native geology adorns almost every building in town. The architecture isn’t even the city’s biggest draw. Oklahoma’s first resort town originally gained acclaim for the healing properties of neighboring Medicine Creek. Today, it’s an adorable little getaway with shops, independent restaurants, and bed and breakfasts that remain little known outside of the plains.

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+8
0
Rating: +8. From 8 votes.
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Astoria, Oregon
#37
Astoria, Oregon, the first permanent U.S. settlement on the Pacific coast, overlooks the Astoria Megler bridge as it crosses the Columbia river to the state of Washington. Photo via Shutterstock.

Astoria, Oregon

Astoria, Oregon, USA

Astoria is probably best recognized as the locale for Goonies (though Haystack Rock sits a little further west near Cannon Beach). The house from the film is still standing, and recently sold in January amid rumors of some sort of tribute museum. Goonies aside, Astoria is a stunning seaside city, where you can enjoy Oregon IPAs with a water view at Buoy Beer Company or take a vintage trolly ride along the Columbia River. Pop by the Oregon Film Museum and learn all this state has contributed movies beyond the Truffle Shuffle.

Do you recommend this?

+18
-5
Rating: +13. From 23 votes.
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Ambler, Pennsylvania.
#38
Exiting the Pennsylvania Turnpike at Route 309. Sign for South 309 toward Philadelphia and Fort Washington and North 309 toward Ambler. Photo via Shutterstock.

Ambler, Pennsylvania

Ambler, Pennsylvania, USA

Ambler is one of the most appropriately named cities in the country, as its walkable downtown encourages everyone to just, well, amble the afternoon away. Its centerpiece movie theater is a Spanish Colonial masterpiece, one of the most architecturally striking cinemas left in the United States. The rest of downtown is no slouch either. You’ll walk past a Barrymore-award winning local theatre company, and fantastic restaurants like the Lucky Well and Gypsy Blu. Ambler also has one of Pennsylvania’s more unique breweries at Forest & Main, whose brewers slings suds out of a converted house on Butler Ave.

Do you recommend this?

+7
-8
Rating: -1. From 15 votes.
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Newport, Rhode Island
#39
Newport, Rhode Island - December 19, 2020: The historic seaside city of Newport, Rhode Island features iconic architecture, whimsical signs and colorful displays of nature. Photo via Shutterstock.

Newport, Rhode Island

Newport, Rhode Island, USA

Newport isn’t exactly a quaint little hidden gem you stumble upon while on a road trip. But it is home to some impressive gilded age mansions, and those clifftop palaces make this town undeniably cool. It’s the best place to experience the Ocean State, with beaches stretching the length of the city and perfect summer sunbathing. Then there’s the city’s sailing. Showing up during regatta week puts you at one of the swankiest waterside parties. Oh yeah, and have you ever heard of the Newport Folk Festival? Or the Newport Jazz Festival?

Do you recommend this?

+38
-2
Rating: +36. From 40 votes.
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Pawleys Island, South Carolina
#40
A dock and walkway on the marshlands of Pawley's Island, South Carolina. Photo via Shutterstock.

Pawleys Island, South Carolina

Pawleys Island, South Carolina, USA

Pawleys Island was the first resort town in the United States, an idyllic oceanside escape for plantation owners and their families during the summer. Some of their lavish digs are still around today, like the pleasant Sea View Inn, and the uncommercialized island is the kind of place where you cross the causeway and feel your blood pressure immediately drop. The adjoining mainland is strewn with mini villages full of shops and restaurants with fresh caught seafood like Chive Blossom and Bistro 217. And the island has easy access to the outdoors, which you can explore by kayaking through calming channels or pedaling along the Waccamaw Neck Bikeway.

Do you recommend this?

+24
-3
Rating: +21. From 27 votes.
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Deadwood, South Dakota
#41
Deadwood, South Dakota. Photo via Shutterstock.

Deadwood, South Dakota

Deadwood, South Dakota, USA

Perhaps you saw the HBO series Deadwood, and assumed a town that lawless and depraved could never survive another century. Well, not only has it survived, it’s maintained almost the same anarchistic appeal, albeit with blank bullets and actors. Deadwood is a perfectly preserved wild west mining town. Old saloons still stand and Buffalo Bill Cody gets killed multiple times a day. The scenic main drag is now filled with casinos, restaurants, and haunted hotels, while the surrounding Black Hills provide endless opportunities to get out and explore nature. Now, outlaw culture has been replaced with family entertainment, making Deadwood a must-stop on any road trip through South Dakota, especially if you have kids in tow.

Do you recommend this?

+14
-11
Rating: +3. From 25 votes.
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Jonesborough, Tennessee
#42
Jonesborough, Tennessee. Photo via Shutterstock.

Jonesborough, Tennessee

Jonesborough, Tennessee, USA

With all due respect to the cavalcade of kitsch that is Gatlinburg, Jonesborough brings a more sophisticated brand of cool to Appalachia. The oldest town in the Volunteer State hosts the National Storytelling Festival, a gathering of creative types and colorful characters that takes over the city every October. When the festival isn’t going on, Jonesborough is a red brick masterpiece nestled in the mountains, a trip back to 18th century America and a fun escape into a landscape of yesteryear.

Do you recommend this?

+61
-8
Rating: +53. From 69 votes.
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Marfa, Texas
#43
Marfa, Texas - March 2018: The Prada Marfa store sits alone at dawn in the middle of the desert. Photo via Shutterstock.

Marfa, Texas

Marfa, Texas, USA

You’ve likely heard of Marfa because of the famous mocked up Prada store (pictured) that artists Elmgreen and Dragset constructed out in the middle of the desert. It’s but one piece in an entire town of modern art, supported by the Donald Judd’s Chinati Foundation and a number of downtown art galleries. With art, of course, comes great food, and this far-flung desert town might be the most surprising place to find spots like Para Llevar from renowned Houston chef Seth Seigel-Gardner, or Cochineal from James Beard nominee Alexandra Gates. Though you can still find plenty of spots for real-deal Mexican food, and cheap beers at the Lost Horse Saloon.

Do you recommend this?

+15
-6
Rating: +9. From 21 votes.
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Moab, Utah
#44
Warm tone and soft light, soft edge, sunset at Delicate arch, Archesh National Park, just north of Moab in Utah. Photo by Shutterstock.

Moab, Utah

Moab, Utah, USA

It would be pretty easy to call Moab the coolest small city in Utah based on its proximity to national parks alone. Both Canyonlands and Arches sit just outside the town, which has become a destination for rugged outdoor types and wandering adventurers. Of course, when tourism becomes your main economic driver, you’ll need some amenities to go with it and Moab definitely delivers. Check out Spitfire Smokehouse for what some might argue is the best BBQ in the state, and a great protein load after a long day playing in the red rocks. Or kick back at Moab Brewery and reward yourself with a Johnny’s American IPA.

Do you recommend this?

+36
-4
Rating: +32. From 40 votes.
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Brattleboro, Vermont
#45
Edge of downtown Brattleboro, Vermont, above the Whetstone Brook River. Photo via Shutterstock.

Brattleboro, Vermont

Brattleboro, Vermont, USA

Often overlooked as New Yorkers speed from the city up to skiing in Killington or Stowe, Brattleboro is a winding little village set alongside the Connecticut River. For leaf peeping, it doesn’t get much better, as crowds don’t descend here like they do in the rest of New England and the views from atop Wantastiquet Mountain are a tableau of bright oranges, reds, and golds. At the base of the mountain, you can stop for a beer at Whetstone Station and drink in two states at once on the patio that straddles the New Hampshire state line. Catch a movie at the historic Latchis Theater, which has a boutique hotel on its upper floors,  or stroll through the storybook downtown and enjoy a hearty meal with a side of people watching at the River Garden Marketplace.

Do you recommend this?

+25
-3
Rating: +22. From 28 votes.
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Washington, Virginia
#46
Little Washington, Virginia / USA - May 6, 2019: Chef Patrick O’Connell is receiving the James Beard Foundation's lifetime achievement award for his three Michelin star Inn at Little Washington. Photo via Shutterstock.

Washington, Virginia

Washington, Virginia, USA

So as not to be confused with the nation’s capital, Washington, Virginia is often referred to as “Little Washington.” The nickname took root  thanks in large part to the iconic Inn at Little Washington that takes up nearly half the town. This Ralaix and Chateaux property is known for its ornate wallpapers and grand verandas as well as for having one of only 14 Three Michelin Star restaurants in the United States. The other, non-resort half of the town is a perfectly preserved artifact of colonial Virginia. Houses surveyed by a young surveyor named George Washington still stand, and much seems frozen in pre-revolutionary times. The Inn recently opened Patty O’s, a not-as-fancy tavern-style eatery with a sunny front patio and croissants so good you’ll wonder if you accidentally drove to France.

Do you recommend this?

+15
-3
Rating: +12. From 18 votes.
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Mount Baker and lighthouse in Port Townsend, Washington. Photo by Shutterstock.
#47
Mount Baker and lighthouse in Port Townsend, Washington. Photo by Shutterstock.

Port Townsend, Washington

Port Townsend, Washington, USA

Not that Western Washington is ever lacking for small waterfront towns with stunning mountain backdrops, but somehow Port Townsend tops them all. This small city on the shores of Puget Sound adds a serious selection of cool architecture to its aesthetic allure with blocks of old Victorian homes filling the streets just off the city’s walkable downtown. Some of those homes are haunted bed and breakfasts, which add a spooky enchantment to the city. The picture perfect setting is part of why Port Townsend was also chosen as the filming site for An Officer and a Gentleman along with nearby Ft. Worden.

Do you recommend this?

+21
-4
Rating: +17. From 25 votes.
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Fayetteville, West Virginia
#48
Fayetteville, West Virginia. Photo via Shutterstock.

Fayetteville, West Virginia

Fayetteville, West Virginia, USA

Fayetteville is like a little slice of Colorado right in the center of Appalachia. The closest town to New River Gorge National Park, it’s populated by river guides, rock climbers and general outdoor enthusiasts. Fayetteville maintains its small-town allure with a few blocks of historic old buildings, and a bed and breakfast at the Historic Morris Harvey House that’s on the National Register of Historic Places. The town has some great places to eat too. Pair inventive pizzas with craft beers at Pies & Pints or fuel up with a long day in the park with sandwiches from the Secret Sandwich Society.

Do you recommend this?

+27
-1
Rating: +26. From 28 votes.
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Lake Geneva, Wisconsin
#49
Lake Geneva, Wisconsin. Photo via Shutterstock.

Lake Geneva, Wisconsin

Lake Geneva, Wisconsin, USA

Back in the late 1800s, this picturesque waterside escape was a bustling resort town for wealthy midwestern industrialists. While it’s a far more accessible destination now, Lake Geneva retained many of the mansions from its first wealthy visitors, which you can see while jogging along the Lake Geneva Shore Path or taking a guided boat tour from Lake Geneva Cruise Line. The city is still a great weekend escape, with a world-class golf resort, fantastic restaurants, a luxury spa and plenty of recreation options on Wisconsin’s second-deepest lake. If you can swing it, stay at the Geneva Inn, a historic old hotel that’s one of the best waterfront hotels in America.

Do you recommend this?

+18
-5
Rating: +13. From 23 votes.
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Dubois, Wyoming
#50
Dubois, Wyoming - August 8, 2021: Exterior of the Country Store Travel Stop gas station, with the famous Worlds Largest Jackalope and selling gifts and ice cream. Photo via Shutterstock.

Dubois, Wyoming

Dubois, Wyoming, USA

Jackson Hole is cool. And it’s small. And it’s also one of those places where you order a Diet Coke at a bar and get sticker shock. For similar small mountain town vibes without the eye-popping pricetag, look about 40 minutes away in Dubois. It’s got the National Bighorn Sheep Center, where you can take a driving mountain safari to see sheep, bison, elk and other great western wildlife. In town, you’ll find steaks as good as chic big city spots at the Lone Buffalo on the same street as bars like the wood-walled Rustic Pine Tavern, where you can sample local beers under mounted elk heads. Just outside Dubois, hit up the National Museum of Military Vehicles, a herculean collection of trucks, helicopters, and other tactical vehicles that tells the story of American warfare through realistic recreations.

Do you recommend this?

+11
-2
Rating: +9. From 13 votes.
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