Driving into Fayetteville, West Virginia, I noticed a sign proclaiming it the “Coolest Small Town.” Of course, I had to wonder: did they just decide that themselves? Did someone else bestow that honor? What did it mean, and why was it on their road sign?
It turns out Fayetteville was named the coolest small town in West Virginia in an article by travel magazine Fifty Grande. (Interestingly enough, the town of Lewisburg, WV, also has road signs naming it the coolest small town, because they were picked by Budget Travel for that honor). Ever since learning about this list, and that apparently at least one town has put enough weight on the title to have custom signs made, I’ve wanted to visit every coolest small town. I haven’t gone as far as planning a trip specifically around them, but many have been easy to visit while traveling full time. Along the way, I’ve learned that some, like Fayetteville, are hidden gems, while others, like Bar Harbor, are the obvious choice.
So, let me share a little about my experiences visiting America’s coolest small towns.
Sedona, Arizona
Sedona is definitely not a hidden gem, and when we visited, it didn’t exactly feel like a small town because of the crowds. We visited for a day while staying in Munds Park, and as much as I can understand why everyone wants to go here, I kind of hated it because of how packed it was. We tried to see the Chapel of the Holy Cross and sat in the car for about 20 minutes before even getting to the parking lot, which was, of course, full. Everywhere we went, it felt impossible to do anything, see anything, park anywhere, or even drive anywhere. I just wanted to get out of there.
But, like I said, I can see the appeal. The red rocks surrounding the town are gorgeous even from a distance, let alone when you’re actually hiking among them. The town also has an artsy vibe, with plenty of galleries and shops to visit. They even have the only McDonald’s with teal arches because the town wanted it to fit their color scheme.
I’ve known people who visit Sedona regularly, but I would definitely only visit it again in the off-season. I’ve heard Sedona in winter is beautiful, and I think that would be a much better way for me to experience it. If you don’t mind the crowds, or can visit in the off-season, some of the most popular hikes are Devil’s Bridge, Cathedral Rock, Soldier Pass, and Boynton Canyon. Montezuma Castle National Monument, just a little outside of town, is worth visiting too. The Montezuma Well unit was actually our favorite part of the day.
Eureka Springs, Arkansas
I definitely need to try Eureka Springs again. I really liked our visit, but we were there in the off-season, and a lot of things were closed. At least half the shops downtown were completely closed for the season, and it seems like there are a lot more events and activities during the on-season. That said, visiting in the off-season was kind of fun because it felt like we were getting more of a locals’ experience. We went to trivia night at Brews and were met by the friendliest locals, who clearly all knew each other but happily invited us to join their teams. One of Josh’s favorite travel stories happened there, too. We walked into a bar and everyone turned to stare at us, only to realize a few minutes later that they were actually watching Jeopardy and playing along. Once the show was over, everyone got up and left. It was absolutely amazing.
One of our favorite spots we visited in Eureka Springs was the Ozark Gothic Thorncrown Chapel. Other popular spots in the area include Christ of the Ozarks, Blue Spring Heritage Center, and Turpentine Creek Wildlife Refuge. Make sure to check out some of the springs around town, too, like Basin Spring in Basin Spring Park next to the historic Basin Park Hotel. Speaking of historic hotels, the 1886 Crescent Hotel is worth visiting as well.
Helen, Georgia
Helen, Georgia, was such a fun spot to visit. It’s a totally Bavarian-themed town in northern Georgia, and walking around the Bavarian-style chalets was so much fun. When you’re downtown, you really do feel like you’re somewhere completely different instead of in the mountains of Georgia. Even though it’s definitely touristy, with plenty of souvenir shops and some cheesy marketing, it’s still incredibly charming and I can see why people enjoy visiting.
There’s plenty of German food to be found around town, which was fun too. We enjoyed a brat and a beer at Troll Tavern, and honestly, leaning into the whole Bavarian theme is part of what makes Helen so enjoyable. You might as well go all in while you’re there. Besides shopping and eating, the Georgia Mountain Coaster is one of the most popular activities in Helen. For something a little more low-key, you can try Alpine Mini Golf or just spend some time wandering around town and taking in all the themed buildings.
Just outside of Helen is the breathtaking Anna Ruby Falls, which is definitely worth adding to a visit. And not far away is the weird and wonderful BabyLand General Hospital, where Cabbage Patch Kids are “born.” Between the mountain scenery, German food, kitschy attractions, and completely unexpected Bavarian architecture, Helen is a pretty unique little town.
Galena, Illinois
Ah, my home state! This is one of the entries on the list where, as soon as I read it, I was like, “Well duh, of course it’s Galena. I should have predicted that.” I’ve been to Galena plenty of times over the years, and it’s a very popular weekend destination for people from northern Illinois, southern Wisconsin, and eastern Iowa.
When I picture a trip to Galena, I picture either a girls’ trip spent shopping and visiting wineries, or a couples’ getaway cozied up in a bed and breakfast. The historic downtown is full of cute shops, restaurants, and old buildings, so it’s easy to spend a whole day just wandering around. But there’s plenty more to do in and around Galena if shopping and relaxing aren’t your thing. You can go hiking, including hiking with goats through Hoof It Goat Treks, or explore the area’s history at sites like the Ulysses S. Grant Home and the Dowling House, Galena’s oldest building. Trolley tours are another popular way to see the town, and the Belvedere Mansion and Gardens is worth a visit if you want to see one of Galena’s historic homes.
Galena is one of those towns that makes for an easy weekend getaway, whether you’re looking for a relaxing trip, some shopping and good food, or a little history and outdoor adventure.
Bar Harbor, Maine
Everyone knows Bar Harbor, so this is another entry that definitely does not fall into the hidden gem category. But it really is a cool town, and when you’re looking just at downtown Bar Harbor, it is a small town. Like most people probably, we visited Bar Harbor as part of a trip to Acadia National Park. Even though it gets pretty crowded with tourists, it very much has that charming small coastal town vibe you want somewhere like this.
If you look a little closer, you’ll see plenty of commercialization, like the Del Sol stores and the jacked-up food prices, but the town itself was founded in 1796, and many of the buildings downtown are authentically old. There’s enough history and character underneath all the tourism that it still feels like a real town rather than just a tourist destination built around Acadia.
Besides the national park itself, some of my favorite things we did in Bar Harbor were walking the land bridge to Bar Island at low tide, strolling the Shore Path, getting coffee and bagels at Choco-Latte Cafe, and shopping at Sherman’s Maine Coast Book Shop, Maine’s oldest bookstore. If we come back again, I’d love to do some kind of boat ride, like a whale watch with Bar Harbor Whale Watch Co. or a cruise with Downeast Windjammer.
Stockbridge, Massachusetts
Apparently everyone knows Stockbridge too, because we were not expecting it to be so crowded! We had a lot of trouble finding parking and had to circle around a few times, which was pretty stressful. We finally found a spot at City Hall, which has free public parking on weekends when the offices are closed. From there, we could easily walk to the downtown shops and restaurants, like the popular Red Lion Inn and Main Street Cafe.
We also visited the Norman Rockwell Museum, which is here because Rockwell lived in Stockbridge and was often inspired by the town and its people. There are plenty of historic house museums to visit as well, including Chesterwood, the former home and studio of sculptor Daniel Chester French, who created the Lincoln Memorial statue, the 18th-century Mission House, and the Gilded Age estate Naumkeag.
Stockbridge definitely has that classic New England small-town charm, but between the popularity of the town itself and all the attractions nearby, it can get surprisingly busy. If you’re visiting, I’d definitely plan ahead for parking and give yourself time to explore beyond just the main street.
Traverse City, Michigan
Even though it was on the list, I did not expect Traverse City to be this cool. Traverse City is the Cherry Capital of the World, and there is no shortage of cherry-themed things to see and eat here, from the world’s largest cherry pie pan to the cherry-red State Theatre.
We loved walking around downtown and stopping at Cherry Republic, where you can sample and buy just about anything and everything with cherries in it. We also stopped at Grand Traverse Distillery to try their cherry whiskey, and I especially loved the two-story Horizon Books. On our second day in town, we grabbed dinner at The Little Fleet, a super fun food truck village with a bunch of different options all in one spot.
Traverse City is also a great jumping-off point for visiting Sleeping Bear Dunes National Lakeshore, which was actually our main reason for coming to the area. Between the fun downtown, the very specific cherry obsession, and the easy access to one of Michigan’s coolest national park sites, I can definitely see why Traverse City earned a spot on the list.
Branson, Missouri
Honestly, I probably wouldn’t have picked Branson for Missouri’s coolest small town. Branson is so cheesy and touristy, and so much of it is overpriced, that I don’t really consider it either cool or a small town. Attractions like the Titanic Museum and Silver Dollar City can be very expensive, although we did splurge on Dolly Parton’s Stampede, one of the town’s many dinner shows.
Downtown has some neat shops, but again, they’re pretty touristy and overpriced. Even the antique stores seem to have tourist prices instead of the normal antique store prices I’m used to. It’s definitely the kind of place where you can spend a lot of money very quickly if you’re not careful. There is some nice nature nearby, though, if you want to escape the crowds and kitsch. Shepherd of the Hills Fish Hatchery and Table Rock State Park are both good options for getting outside and seeing a different side of the Branson area.
Deadwood, South Dakota
Deadwood is another interesting entry on the list. On one hand, there is a lot of really cool history here, but walking around town, the “coolness” can also feel pretty manufactured. Deadwood was founded in the 1870s during the Black Hills Gold Rush and quickly became a wild frontier town known for gambling, drinking, and its colorful characters. Wild Bill Hickok was famously killed here in 1876, and Calamity Jane is also closely associated with the town.
There’s plenty of real history if you look for it, but there’s also lots of tourist kitsch and Old West exaggeration. We still had fun walking around downtown, and especially liked visiting the Deadwood Brothel Museum and Mount Moriah Cemetery. We were also lucky enough to be there for the Days of ’76 Parade, which was a fun way to see the town really lean into its Old West history.
We didn’t get to all of the museums, but if we were to go back, I’d also like to visit the Adams Museum, Historic Adams House, and Days of ’76 Museum. Deadwood was historically known for gambling, and there are still plenty of casino options today, including Mineral Palace Hotel and Cadillac Jack’s. There are also lots of themed shops downtown, like Deadwood Outfitters and Miss Kitty’s Mercantile, for all your Old West souvenir needs.
Deadwood is definitely a little cheesy, but I think the combination of genuine history and over-the-top Old West tourism is part of what makes it interesting.
Fayetteville, West Virginia
The town that started this whole journey. We’ve visited Fayetteville twice now while also visiting New River Gorge National Park (well, the first time we went, it wasn’t a national park yet). After three years of traveling the country full-time, Fayetteville is still one of my favorite towns I’ve ever visited.
It’s a little quirky, the first time we visited, there were flower planters made out of doll heads scattered around town. It’s a great mix of a little weird, clearly more liberal than a lot of the state, and surrounded by beautiful nature. Exactly my vibe. We also had amazing food everywhere we went. We ate at Pies & Pints multiple times, I still think about Secret Sandwich Society a lot, and I loved both the food and the vibes at Cathedral Cafe.
Out of all the coolest small towns we’ve visited so far, Fayetteville is still the only one we’ve seen actually proclaiming it on a town sign. And as far as I’m concerned, it is THE coolest small town in America.
