The Quick Report

The Coolest Small City in Every State

America’s small towns are often overlooked. Fascinating history and old-time charm live in these forgotten places, existing arm-in-arm with modern arts, great food, and culture. Here are the coolest small cities in every state.

1. Alabama: Orange Beach

Alabama Orange Beach

Orange Beach is the epicenter of Alabama’s stretch of the Gulf Coast. It features white-powdered sand that rivals Florida. This strip of beach features high-rises and is home to the famous Flora-Bama Roadhouse. You can rent a bike and explore over 28 miles of trails inside Gulf State Park. You’ll find some of Alabama’s best restaurants here too.

2. Alaska: Sitka

Alaska Sitka

The largest US city size-wise, Sitka encompasses over 2,800 square miles. Outdoor recreation is abundant. Hike to Mt. Edgecumbe and see the Caldera Volcano. Paddle around the coastal islands on a kayak. Hike to the top of Harbor Mountain to view stunning Alaska wilderness. See native birds at the Alaska Raptor Center dining on the freshest seafood to be found.

3. Arizona: Sedona

Sedona Arizona

The spectacular red, clay-colored cliffs of Sedona are a sight to behold. Take a jeep tour, or hike to the Devil’s Bridge and Cathedral Rock trails. The town draws artists and those seeking spiritual energy and psychic readings. Visit a sweat lodge. You’ll find high-end dining and casual fare. Plus, you’ll find a wide variety of spectacular southwestern food.

4. Arkansas: Eureka Springs

Eureka Springs Arkansas

The city’s water springs are said to have healing powers. Tales of miracles spread nationwide in the 1800s. It remains a place for religious pilgrimages. This enclave in the Ozarks is home to a hippie commune and a nudist Airbnb. Check out its Victorian-style architecture, or the 66-foot statue of Jesus Christ. Visit the haunted Crescent Hotel and Spa.

5. California: Carmel by the Sea

California- Carmel by the Sea

This city feels like a European village with its maze of cottage-style architecture. However, it’s an upscale town with chic celebrity hangouts. Its access to the ocean draws a well-heeled crowd. Explore the tide pools and go whale watching all year long. Clint Eastwood once served as town mayor.

6. Colorado: Telluride

Colorado Telluride

This former mining town in southwestern Colorado isn’t easy to access. After your flight, it’s a few hours’ drive through national forests. Its main Street is one of the most photographed in the country. It’s legendary for its late-partying watering holes. It annually hosts Jimmy Buffett’s Blues and Brews Festival and a celebrity-filled film festival on Labor Day weekend.

7. Connecticut: Mystic

Connecticut- Mystic

The 1988 film Mystic Pizza made the town famous. But before the movie, vacationers flocked here to enjoy this seaport. Rent boats and paddle boards and float past stately and historic homes. Visit the Mystic Aquarium or Seaport Museum. For the true oceanside New England experience, hang with the locals in its bars and restaurants.


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8. Delaware: Bethany Beach

Delaware- Bethany Beach

Here’s a great spot to enjoy the mid-Atlantic coastal vibe in a far more relaxed setting. Meander along the boardwalk and take photos along its half-mile of its whitewashed buildings and landmark clock. You’ll find fantastic seafood at its popular restaurants that are a notch above the standard beach fair. Take a stroll through Delaware Seashore State Park.

9. Florida: St. Augustine

Florida St. Augustine

America’s oldest established city, it’s a gem of history, nature, and great food. Take a tour of the old city or a ghost tour past the haunted bars and the Spanish fort Castillo de San Marcos. Visit St. Augustine Alligator Farm and zipline over pits of hungry alligators. Then cross the Intracoastal to some of the more secluded Florida beaches.

10. Georgia: Helen

Georgia- Helen

Travel through Georgia’s Blue Ridge Mountains and go north on Highway 75, and you’ll find yourself in the heart of Bavaria. This German-themed town is filled with Biergartens, chocolate shops, and plenty of schnitzel. A little outside of town, you’ll find some of Georgia’s best wineries. Not much farther yonder is the Chattahoochee River, with great fishing and whitewater rafting.

11. Hawaii: Koloa

Hawaii- Koloa

Old Koloa Town has something different than any of the other Hawaiian island’s coastal drives offer. The vibe is like a tropical Old West, retaining the look of the early days of European Hawaii settlement. It features the state’s first sugar plantation and you’ll learn the sugar industry’s history. There are also coffee roasters, souvenir shops, and art galleries.

12. Idaho: Sandpoint

Idaho- Sandpoint

Located on the shores of Lake Pend Oreille, there’s a lot here. You can volleyball and tennis on the city beach, or tan while viewing the mountains. A big draw is the Schweitzer Mountain Resort. There’s also a Jack Nickalus-designed golf course, craft breweries, and the Silverwood Theme Park and Boulder Beach Waterpark. The Clark Fork River offers whitewater rafting.

13. Illinois: Galena

Illinois- Galena

Three hours from Chicago, you’ll find Midwestern charm that harkens from the past. You can stroll some main streets right out of the history books. Learn blacksmithing, tour opulent mansions, visit art galleries and fascinating boutiques. Visit Horseshoe Mound for one of the best viewpoints in the state.

14. Indiana: Madison

Indiana- Madison

The longest contiguous National Historic Landmark in the US is found here. Located along the Ohio River, the entire town is one big historic district. Its architecture is Federal, Greek Revival, and Second Empire. Riverboat cruises stop here. Downtown features wineries, bars, and restaurants easy to visit with a short port call. For thrills, check out the New Zealand jetboat.

15. Iowa: Grinnell

Iowa- Grinnell

Grinnell combines midwestern ethos with college-town progressiveness. Its downtown is highly walkable. The Louis Sullivan Jewel Box Bank is a national historic landmark designed by the “father of the skyscraper.” It’s now Grinnell’s visitor’s center. Whether sipping Chardonnay at a wine bar or eating at the counter in a diner, the crowds look the same. Stay at the Hotel Grinnell.

16. Kansas: Humboldt

Kansas- Humboldt

This sleepy rural town of barely over 1,800 people has been revitalized. A destination for campers, they flock to Base Camp, a full-service campground with instant access to the Prairie Spirit Trail. Downtown has exploded with big-city-style restaurants. Humboldt is now acclaimed for places such as Honeybee Bruncherie and its famed interior, as well as its candy shop, Bijou Confectionary.

17. Kentucky: Bardstown

Kentucky- Bardstown

Billing itself as the bourbon capital of the world, it’s home to Maker’s Mark, the Jim Beam American Stillhouse, and Bardstown Bourbon Company. Beyond distillery tours, the main drag along Highway 150 reflects the old South. You’ll find restaurants, as well as bars with an almost overwhelming selection of whiskey, and some of the best spirits in the world.

18. Louisiana: Slidell

Louisiana- Slidell

Slidell rests along Lake Pontchartrain’s North Shore and is less than 45 minutes from the French Quarter. It’s home to one of the largest antiques districts in the state, with fairs twice annually drawing thousands. Downtown features art galleries, antique shops, and more. Try the Honey Island Swamp Tour to see the alligators and animals that call the Bayou home.

19. Maine: Bar Harbor

Maine- Bar Harbor

This seaside haven has a look and feel nearly identical to the fictional Cabot Cove of the TV series Murder, She Wrote. The warmer seasons offer a variety of things to do such as sailing, fishing, fresh seafood joints, ice cream shops, and visiting quaint family-run stores. It’s also the gateway to Acadia National Park.

20. Maryland: Frostburg

Maryland- Frostburg

Within the Allegheny mountains, you’ll find this jumping-off point of the Great Allegheny Passage. It attracts outdoorsy and mountain types year-round. You’ll find classic small-town eateries on its brick-lined downtown streets. They lead to a trailhead that branches to Cumberland in one direction, and Pittsburgh in the other. Hop on the Western Maryland Scenic Railroad for sightseeing and comfort.

21. Massachusetts: Stockbridge

Massachusetts- Stockbridge

If this town feels like a Norman Rockwell painting, it’s because much of his work was inspired by Stockbridge. The town is the home of the Norman Rockwell Museum. You’ll find a large collection of historic homes and museums, including the Clark Art Institute. In winter, the town transforms into a Christmas wonderland and another classic image of Americana.

22. Michigan: Traverse City

Michigan- Traverse City

Bordered by the Grand Traverse Bay of Lake Michigan, it’s the gateway to nature and the Sleeping Bear Dunes National Lakeshore. A trail of 40 wineries sits just outside the city, and Leelanau Peninsula is one of the most underrated wine regions in the world. There’s something for every season here, with skiing at the Crystal Mountain Resort.

23. Minnesota: Grand Marais

Minnesota- Grand Marais

Located off one of America’s most scenic drives, Highway 61 on Minnesota’s North Shore, and 40 miles from Canada, it’s a must-stop. Its Scandinavian heritage is evident everywhere. You’ll find some of the state’s best pizza, as well as other cool ethnic eateries downtown. Visit some of the local breweries, or satisfy your sweet tooth with ice cream or doughnuts.

24. Mississippi: Ocean Springs

Mississippi- Ocean Springs

Located just east of Biloxi, rests this artsy village and beach destination with beautiful white sand. Stay at the floating cabins at the Beatnik Hotel. There’s an open container district where you can bar hop along Government Street and take in several live bands in one night. Good food and art are abundant. Visit the Walter Anderson Museum of Art.

25. Missouri: Branson

Missouri- Branson

Sometimes called “the Nashville of the Ozarks,” Branson is filled with entertainment and theme parks. Many of country music’s biggest stars perform here regularly. Ride mountain coasters, giant slingshots, and hear live music revues. Silver Dollar City is an old-west theme park featuring high-speed coasters. You can also visit the Titanic Museum, featuring a full-scale mockup of the doomed liner.

26. Montana: Livingston

Montana- Livingston

Born as the gateway to Yellowstone, this city is home to an influx of transplants but still has Old West grit. Restaurants are superb as world-class chefs have migrated here. Downtown houses numerous country bars with crowds and live bands hailing from all over. There’s fly fishing year-round on the river, and the park is less than an hour away.

27. Nebraska: McCook

Nebraska- McCook

In the Old West, McCook was an oasis of civilization among the vast western prairies and the stagecoach and train era. Today, it’s home to a brand-new art district, as well as annual storytelling and music festivals. There’s a James Beard award-winning bakery and Nebraska’s only Frank Lloyd Wright-designed house.

28. Nevada: Virginia City

Nevada- Virginia City

This is the destination for those who want to see the immaculate preservation of an Old West mining town. Check out the iconic Piper’s Opera House, which still hosts live performances. There’s also modernity and a lot of wacky fun, like the annual World Championship Outhouse Races or the International Camel and Ostrich Races that outdraw some professional sports teams!

29. New Hampshire: Lincoln

New Hampshire- Lincoln

This small town of 1,600 people is home to the Loon Mountain Resort with lots of narrow, high-speed runs. The resort also has an on-site winery to reward yourself after a long day of skiing. In the summer, explore Franconia Notch State Park with some of the best hiking and mountain biking in the state.

30. New Jersey: Asbury Park

New Jersey- Asbury Park

This city’s boardwalk is famous. Ride the roller coaster and check out the Victorian homes along the Jersey Shore. The Asbury Ocean Club is a five-star hotel. The Asbury Hotel features a Victorian-meets-rock ‘n’ roll motif. And the Stone Pony is where rockers like Bruce Springsteen and Jon Bon Jovi got their start. 

31. New Mexico: Chimayo

Chimayo New Mexico

This city is famous for its weaving families who make unbelievable crafts. It’s also home to an adobe church named El Santuario de Chimayo built in the early 1800s. It’s worth a visit for its architecture and ornate design alone. Check out the adobe-style hotel Rancho de Chimayo and dine on traditional New Mexican cuisine under the desert sky.

32. New York: Cooperstown

New York- Cooperstown

Nestled along the shores of Otsego Lake in the Catskills everything in this town is about baseball. It’s home to the National Baseball Hall of Fame. Cooperstown is also amazingly scenic. Have a waterfront meal, enjoy local craft beers, and browse souvenir shops. Its “Anytown USA” downtown is full of nostalgic charm.

33. North Carolina: Boone

North Carolina- Boone

Home to Appalachian State University, it has a strong college-town vibe. There’s a homey feel to the streets of downtown. Besides great restaurants, diners, and bars, its appeal is in outdoor recreation. Check out Blowing Rock or the biosphere reserve at Grandfather Mountain. Take in high country sightseeing on the Tweetsie Railroad. Don’t miss the scenic hillside wineries.

34. North Dakota: Medora

North Dakota- Medora

Outside the Theodore Roosevelt National Park, set among the Burning Hills, this little town has reinvented itself. Its historic Western downtown has been restored and renovated. It’s a great summer visit. You’ll find one of the coolest music venues in the country at the Burning Hills Amphitheater. Explore the park, and be sure to see the Medora Musical.

35. Ohio: Put in Bay

Ohio- Put in Bay

This little island on Lake Erie is often called “The Key West of the North.” Visit the Crystal Caves, an underground cavern with the world’s largest geode and an onsite winery. The walkable downtown features restaurants and souvenir shops. Summer is the busy season and feels like three straight months of spring break with nonstop raging pool parties at hotels.

36. Oklahoma: Madison Park

Oklahoma- Madison Park

Stunning native geology adorns almost every building in town. But the biggest draw to this area has always been the healing properties of Medicine Creek, which turned this into Oklahoma’s first resort town. This adorable gateway to nature features shops, independent restaurants, and bed and breakfasts. This quaint locale is one of the best-kept secrets of the plains.

37. Oregon: Astoria

Oregon- Astoria

If you’ve seen the movie The Goonies, you’ll recognize this locale. The house from the film is still standing. This stunning seaside city is a great place to view the water while sipping local brews. Take advantage trolley ride along the Columbia River. Drop by the Oregon Film Museum and check out this state’s legacy beyond the “Goon Docks.”

38. Pennsylvania: Ambler

Pennsylvania- Ambler

This aptly named city features one of the most walkable downtown areas in the country. It’s home to one of the most architecturally striking cinemas still standing in the US, a Spanish colonial masterpiece. Its local theater company is Barrymore-award-winning. Fantastic restaurants, breweries, and shops abound.

39. Rhode Island: Newport

Rhode Island- Newport

You’ll find the past astonishingly preserved here, as its gilded age mansions and cliff-top palaces are a sight to behold. Beaches stretch the length of the city. It’s a great destination for summer sunbathing or sailing. It’s world-famous for its Newport Folk Festival and Newport Jazz Festival. During Regatta week, you’ll find plenty of swanky waterside parties.

40. South Carolina: Pawleys Island

South Carolina- Pawleys Island

Considered the first resort town in America, it served as a summer oceanside retreat for plantation owners and their families. Some of their lavish homes still stand. The mainland is strewn with mini villages and a slew of shops and restaurants offering freshly caught seafood. Abundant outdoor activities include kayaking or peddling along the Waccamaw Neck Bikeway.

41. South Dakota: Deadwood

South Dakota- Deadwood

Featured in the HBO series of the same name, this Old West mining town is perfectly preserved today. However, its scenic main drag is now also populated with casinos, haunted hotels, and restaurants. Take in a Western show and see Buffalo Bill Cody get killed multiple times daily. There’s lots of family entertainment. The surrounding Black Hills offers nature exploring.

42. Tennessee: Jonesboro

Tennessee- Jonesboro

Within Appalachia sits the oldest town in the volunteer state. Nestled in the mountains, it’s a red-brick masterpiece that will take you back to 18th-century America. It feels like yesteryear here. It’s also home to the National Storytelling Festival in October when creative types and colorful characters take over the town.

43. Texas: Marfa

Texas- Marfa

What you’ll find in this far-flung desert town will certainly surprise you. It gained fame after artists Elmgreen and Dragset constructed a mocked-up Prada store in the middle of the desert. The town itself is filled with numerous art galleries downtown. They’re surrounded by excellent food, great chefs, authentic Mexican food, and plenty of spots to grab a beer.

44. Utah: Moab

Utah- Moab

Famous for its proximity to national parks, arches, and Canyonlands, it’s become a major destination for outdoor types and adventurers. With the tourism in the Red Rocks, comes an influx of amenities, great food, and breweries. They all add up to making Moab one of the coolest small cities in Utah.

45. Vermont: Brattleboro

Vermont- Brattleboro

This village alongside the Connecticut River is one of the best destinations in New England for fall colors. The best views are atop Wantastiquet Mountain. At the base, drink beer in two states at once at Whetstone Station, which straddles Vermont’s state line. Visit the storybook downtown area and people-watch at the River Garden Marketplace.

46. Virginia: Washington

Virginia_ Washington

Its iconic inn, Little Washington, takes up nearly half the town. This Ralaix and Chateaux property is known for its grand verandas, ornate wallpapers, and Three Michelin Star restaurant The remaining non-resort half of town perfectly preserves colonial Virginia. Houses still stand that our founding father George Washington surveyed.

47. Washington: Port Townsend

Washington- Port Townsend

This small waterfront town on the shores of Puget Sound offers stunning mountain backdrops. You’ll find a serious collection of cool architecture here, as well as blocks of old Victorian homes. The city’s downtown is highly walkable. You’ll find haunted bed and breakfasts, as well as excellent restaurants and bars.

48. West Virginia: Fayetteville

West Virginia- Fayetteville

Located right in the center of Appalachia, it’s the closest town to the New River Gorge National Park. The town’s population is full of river guides, rock climbers, and assorted outdoor enthusiasts. Small-town allure abounds here, with blocks of historic old buildings, some on the National Register of Historic Places. There are great eateries, pizza joints, and craft beer bars.

49. Wisconsin: Lake Geneva

Wisconsin- Lake Geneva

In the 1800s, this was a picturesque resort town for the wealthy. Many mansions still stand and can be viewed along the Lake Geneva Shore Path or via a guided boat tour. You’ll find a world-class golf resort, amazing restaurants, a luxury spa, and lots of recreation options. The Geneva Inn is one of the best waterfront hotels in America. 

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50. Wyoming: Dubois

Wyoming- Dubois

Find small-town mountain vibes on the cheap here. Order steaks as good as any big city restaurant and sample local-brewed beers. Visit the National Bighorn Sheep Center for a driving mountain safari. See sheep, bison, elk, and other wildlife. Just outside Dubois, see the National Museum of Military Vehicles. A massive collection of machinery and American warfare through realistic recreations.

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