What does it feel like to live in the Coolest Small Town in America? Ask the folks in Grand Marais, Minnesota, who earned the top spot in our 10th annual contest. Their town showed us the perfect blend of edgy, sweet, beautiful, and travel-worthy that adds up to “cool” in our book. Read on to stoke your wanderlust.
#1 GRAND MARAIS, MN: Paddler’s paradise on Lake Superior (pop.: 1,351).
Get your canoe on! Here on the north shore of Lake Superior, the Boundary Waters Canoe Area is one of the world’s perfect paddling destinations, with miles of waterways to navigate. Whether you’re craving a romantic getaway or a real adventure, Grand Marais has a little something for everyone, including cozy B&Bs, a vibrant arts community, an annual Fisherman’s Picnic, Superior National Forest, and restaurants whose names say it all: Angry Trout Cafe, World’s Best Donuts, and Sven and Ole’s Pizza!
#2 CHINCOTEAGUE, VA: A mid-Atlantic island escape (pop.: 2,941).
This incredibly beautiful island town offers a mid-Atlantic summer getaway complete with perfect beaches with trails for cycling and walking, fresh seafood (and an annual seafood festival!), and its legendary wild ponies. But it’s also a year-round hot spot, especially during its holiday parades and house tours. The town is also a favorite spot for amazing boat tours and as an ideal locale for watching NASA rocket launches from the nearby Wallops Visitor Center.
#3 HILLSBOROUGH, NC: Art and literature come alive in the mountains (pop.: 6,087).
Talk about local spirit! Hillsborough amassed the most nominations this year to make our list of semifinalists. The town has serious literary cred, with several bestselling authors not only making their home here but also participating in local events and the annual production of “A Christmas Carol.” Enjoy the newly opened Riverwalk trail, Last Fridays Arts Walks, historical buildings dating back to the 18th century, and Occoneechee Mountain. Top-notch local restaurants offer live music, and you may even spot the mayor on a night out. (You’ll know him by his signature bowler hat!)
#4 ALLEGAN, MI: Mayberry on the Kalamazoo River (pop.: 4,998).
Locals sometimes refer to Allegan as a “modern-day Mayberry,” and we can understand why. Friendly eateries like The Grill House, Minnie Sophrona’s Restaurant, and Corky’s Drive-In, plus an old-timey movie theater and much more, make visitors feel at home here. And with the lovely Kalamazoo River winding its way through town and Allegan’s proximity to Lake Michigan, inland lakes, and ski resorts, all four seasons can be filled with outdoor fun and natural beauty. Whether you’re craving a thriving food and art scene, a buzzworthy county fair, or you just love fishing (including ice fishing!) or golf, Allegan is a warm and welcoming getaway.
#5 WASHINGTON, NC: A Southeast sailing mecca (pop.: 9,744).
Locals like to say that Washington has a small-town feel but big-town activities. The waterfront downtown is a major draw, with a renovated theater, wonderful shops, and a wine-tasting scene that surprises some visitors. The Pamlico River is popular with the sailing crowd 10 months of the year, and hunting and fishing are thriving activities in the area. Founded in 1776 and named for General George Washington years before he became our nation’s first president, this town wears its history proudly but lightly, sometimes referring to itself as “Little Washington.”
#6 DELHI, NY: Galleries, antique shops, and a film festival in the Catskills (pop.: 3,087).
The western Catskills in Upstate New York make for a wonderful setting, with rolling hills and the Delaware River (yes, its western branch reaches all the way up here) flowing through town. A thriving Main Street is ideal for browsing eclectic galleries, antique shops, and an artisan guild that features local talent. If you ever tire of exploring the hiking trails and enjoying water sports on the river, get ready for the Catskill Mountains Film Festival, the Delhi Covered Bridge Run, and the Taste of the Catskills food festival, among other crowd-pleasers in this popular town.
#7 FORT MYERS BEACH, FL: This perfect island town is your gateway to the Everglades (pop.: 6,277).
On Estero Island, on Florida’s southwestern coast, Fort Myers Beach should not be confused with the nearby city of Fort Myers. Here, everybody knows everybody, and you’re never more than a mile or so from the sparkling waters of the Gulf of Mexico. Think of this as your entry point for exploring this remarkable stretch of coastline, including gorgeous islands, Everglades National Park, and creatively prepared local seafood at restaurants such as The Beached Whale and Matanzas on the Bay.
#8 HURON, OH: Beaches, craft beer, and live music on Lake Erie (pop.: 7,149).
Where the Huron River meets Lake Erie, one of the Midwest’s hidden gems is waiting for you. Go hiking at Sheldon Marsh State Nature Preserve, visit the Huron Pier for some great fishing, relax on Nickel Plate Beach, or hit the local golf course. You can enjoy this town just by taking a leisurely stroll along downtown’s waterfront streets and visiting the scenic boat basin for photo ops or one of the town’s many festivals. Craft beer and live music are both on tap downtown as well, and you can take your pick of lodgings, from a resort experience to a comfy B&B.
#9 SNOHOMISH, WA: Quirky festivals in the Pumpkin Capital of the Pacific Northwest (pop.: 9,098).
With idyllic rolling farmland, Puget Sound, and the Cascade Mountains as a backdrop, this town is a Pacific Northwest paradise just a short drive from Seattle. Activities here are as big as all outdoors, with hot-air ballooning, sky-diving, and unique local festivals such as “GroundFrog” Day and the Easter Parade, with its Sauerkraut Band. You can bike or walk the Centennial Trail, be one of the first to see the brand-new aquatic center, and enjoy downtown Snohomish’s excellent restaurants and justly famous antique shops. In fall, this is the Pumpkin Capital of the Northwest!
#10 OLD ORCHARD BEACH, ME: An iconic boardwalk and perfect stretch of New England beach (pop.: 8,624).
There’s more to this town than its namesake beach, though truth be told the seven-mile stretch of sand is awesome in its own right, with its legendary amusement park and nightlife that includes live bands and great seafood. But Old Orchard Beach is also a prime base for kayakers who want to explore area rivers, fishermen or day-trippers who crave a cruise out on the Atlantic, and those of us who are content to contemplate beautiful lighthouses (like nearby Cape Elizabeth) and watch the tide roll in and out.