Main Street, Sykesville, Maryland
— Sykesville Main Street Association
SYKESVILLE, MD (continued) Visit the weekly farmers market for a taste of the region’s bounty, then sit down for a hearty meal of pub grub, crepes, and other local treats.
NO. 2: PIPESTONE, MN (pop. 4,157) Pipestone National Monument, with its Sacred Quarries, gives the town its name. Here, Native Americans obtained distinctive red stone for carving ceremonial pipes.
— Joe Ferrer/Dreamstime
PIPESTONE, MN (continued) The town’s Circle Trail takes you past the quarries and the inspiring Winnewissa Falls. Take a local “ghost walk” (at least one hotel, Calumet Inn, is said to be haunted) or explore the region’s Civil War history. Classic American fare is the name of the game in historic downtown, and while you’re there you must tour the colorful quartzite buildings.
— Julie Carrow/Pipestone Area Chamber of Commerce & Visitor Bureau
NO. 3: BAKER CITY, OR (pop. 9,769) When your town is bordered by the beautiful Elkhorn and Wallowa mountains in northeast Oregon, and resides at the intersection of not two but three Oregon Scenic Byways, you know you’ve got a good thing going.
— Baker County Tourism
BAKER CITY, OR (continued) The town’s restored downtown encourages travelers to relax and stay a while with outdoor cafes, First Friday Art Walks, the Taste of Baker City celebration, and even carriage rides through the historic district.
— Baker County Tourism
NO. 4: FAIRPORT, NY (pop. 5,338) New York State’s Erie Canal played a major role in making the downstate metropolitan area a major port and economic powerhouse. These days, the canal supplies another kind of power: Natural beauty along Fairport’s popular promenade.
FAIRPORT, NY (continued) The village itself is lined with lovely storefronts and restaurants that offer classic comfort food befitting a town that residents describe as “front-porch friendly.” Outdoor activities include a number of walking trails and, of course, boating on the canal.
NO. 5: ABINGDON, VA (pop. 8,191) With the Blue Ridge Mountains as a backyard and a charming, historic downtown, Abingdon has been drawing visitors for more than two centuries. In fact, The Tavern restaurant dates back to 1779.
— Sam Dean/Abingdon Convention & Visitors Bureau
ABINGDON, VA (continued) Catch a play at the Barter Theatre (named for the founding Depression-era actors, who used to trade show tickets for food), bike the gorgeous Virginia Creeper Trail, and look for a “Rooted in Appalachia” sign at local restaurants for fresh, locally sourced seasonal ingredients. Bunk down at the swanky Martha Washington Inn and Spa, a Four-Star Historica Hotel and local landmark.
— Jason Barnette/Abingdon Convention & Visitors Bureau
NO. 6: KIDRON, OH (pop. 944) In the heart of Ohio’s Amish country, Kidron is decidedly retro-chic, drawing visitors who appreciate an authentic old-timey general store, vintage tool shops, unique furniture and antiques, and comfy nearby B&Bs.
KIDRON, OH (continued) For a taste of real country life, be sure to attend a flea market and livestock auction, which draw farmers and their families from the surrounding countryside, sometimes driving iconic Amish buggies.
NO. 7: OCEAN SPRINGS, MS (pop. 17,493) A Gulf coast town with a thriving downtown, bike trail, and the Gulf Islands National Seashore? We’re there!
OCEAN SPRINGS, MS (continued) Whether you crave wildlife encounters that include ‘gators at the national seashore, a cool local brewery scene, or the chance to walk to nearby Biloxi for views of the bay, Ocean Springs will keep you busy. Of course you’re going to find great BBQ, catfish, po’ boys, and tables with sparkling Gulf views.
NO. 8: NILES, MI (pop. 11,430) Artisanal chocolate, beautiful architecture, a stunning riverfront park… We had you at “artisanal chocolate,” didn’t we?
NILES, MI (continued) Niles’s proximity to Chicago, Lake Michigan beaches, and Notre Dame University have made it a coveted travel experience for Midwesterners looking for unique antiques, history, and tours of the impressive Chapin Mansion. Hungry? Drop by Jim’s Smokin’ Cafe, Brew Ha Ha, or the alluringly named Viking Grill.
— Michigan Municipal League/Flickr
NO. 9: TAOS, NM (pop. 5,731) How do you define a cool town? A UNESCO World Heritage site? A rafting adventure? A haunted cantina? Yes, Taos sure sets the cool bar high.
— Giuseppe Masci/Dreamstime
TAOS, NM (continued) It’s home to historic Taos Pueblo, rafting tours of the Rio Grande, the adobe Alley Cantina (where, in theory, you can sip a margarita and see a ghost at the same time), and much more. Ride the Taos Ski Valley lift, say “aaaaah” when you dip into the natural hot springs, or book yourself an awe-inspiring hot-air balloon ride above it all.
— Giuseppe Masci/Dreamstime
NO. 10: STEAMBOAT SPRINGS, CO (pop. 12,100) Yes, you can spend your days hiking, kayaking, and climbing in the Rockies and your evenings sipping world-class wines and digging into imaginative cuisine that may make you feel as if you’ve been transported temporarily to a big-city restaurant.
— Steamboat Springs Chamber Resort Association
STEAMBOAT SPRINGS, CO (continued) In Steamboat Springs, you can have it all, including western heritage, natural beauty (which can be enjoyed from above in a hot air balloon!), and a touch of urban sophistication to boot. In winter, powder is what visitors are after, and the area obliges with incredible ski trails; in summer, those same trails and gondolas deliver a dreamy outdoor adventure experience.
— Riley Seebeck/Dreamstime
Budget Travelers know there's no cooler vacation than an all-American vacation, and our 11th annual Coolest Small Town in America contest stirred up excitment and heated competition from the moment nominations opened this winter to the close of voting on June 6. We've loved learning so much about these great places to eat, stay, and play, and we hope you'll get to know them too!