PHOTOS: Coolest Small Towns in America 2015

North House Folk Schools sailboat, Hjordis, leaving the harbor in Grand Marais, MNDowntown Grand Marais, MNBike-friendly Town in Chincoteague, VA
Island Library in Chincoteague, VAHillsborough's Churton Street was named Great Main Street in 2012 as part of the Great Places in North Carolina initiativeCST-2015_Hillsborough_North-Carolina_riverwalk
CST-2015_Allegan_Michigan_Riverfront_walkMain Street in Allegan, MichiganLittle Washington, North Carolina
Washington North Carolina's Historic Harbor District and docksCourthouse Square in Spring Delhi New YorkFishing along the Delaware River in Delhi New York
Beautiful beach near the pier and Fort Myers Beach's Time Square area, FloridaTimes Square in Fort Myers Beach, considered the heart of Estero Island's downtown with shops, restaurants and the Fort Myers Beach PierLakefront View in Huron, OH
The annual Boppin' by the Basin in Huron, OHKids were having fun on weekend at a local pumpkin patch farm in Snohomish near SeattleThe main street in Snohomish, Washington
The Pier at Old Orchard Beach, Maine is a popular summertime destination visited by people from all over the world. Located on the coastline of the Atlantic Ocean.Old Orchard Beach in Maine, USA is a popular summer destination. With its 7 miles of sand, and tourist-oriented businesses, it provides seashore fun.
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#1 GRAND MARAIS, MN: 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.

Courtesy Visit Cook County Minnesota

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!

Courtesy Visit Cook County Minnesota

#2 CHINCOTEAGUE, VA: This incredibly beautiful island town offers a mid-Atlantic summer getaway complete with perfect beach­es with trails for cycling and walking, fresh seafood, and its legendary wild ponies.

Courtesy Chincoteague Chamber of Commerce

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.

Courtesy Chincoteague Chamber of Commerce

#3 HILLSBOROUGH, NC: 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.”

Courtesy Donn Young/Orange County Visitors Bureau

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!)

Courtesy Donn Young/Orange County Visitors Bureau

#4 ALLEGAN, MI: 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.

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.

#5 WASHINGTON, NC: 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.”


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.

Courtesy Little Washington NC

#6 DELHI, NY: 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.

Patti Woznick

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.

Patti Woznick

#7 FORT MYERS BEACH, FL: 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.

Courtesy Lighthouse Island Resort

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.

Courtesy Lighthouse Island Resort

#8 HURON, OH: 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.

Jennifer B. Kilbury

#9 SNOHOMISH, WA: 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!

Courtesy Snohomish County Tourism Bureau

#10 OLD ORCHARD BEACH, ME: 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.


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.


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.

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