37 Most Charming Towns in America

By Jody Vandergriff @chiefseeker

Planning to hit the road this summer? Check out these charming towns across America gushing with personality and history.

Most Charming Towns in America Map

Williamsburg

Together with Jamestown and Yorktown, Williamsburg is part of the historic triangle - the stomping grounds for America's OGs. At its center, Historic Williamsburg is the place to see living museum, with real actors depicting scenes from the American Revolution.

August 11, 2020
Gatlinburg

This charming, southern town is the gateway to the Great Smoky Mountains National Park.

August 11, 2020
Monterey

Beautiful seaside town in Northern California. The aquarium is THE BEST around.

August 12, 2020
Breckenridge
St. Augustine
Bar Harbor
Steamboat Springs
Moab
Sedona
Jackson Hole
Columbia

Such a fun, historic Gold Rush town. There are a ton of activities for kids like panning for gold and horse and carriage rides. Columbia is a perfect stop on the way to Yosemite.

August 12, 2020
Ely
Ouray
Montpelier
Nantucket
Kennebunkport
Wallace
Hilo
Essex
St. Helena

There are so many adorable towns in the Napa/Sonoma wine country region, but St Helena stands out from the crowd. In fact, it boasts the nickname "Napa Valley's Main Street." Stop here to browse local art, shop the quaint boutiques featuring unique goods or enjoy a glass of world class wine at one of the many highly rated restaurants.

August 12, 2020
Old Town
Mancos
Placerville
Unalaska
San Clemente
Ojai
Nevada City
Murphys
Lone Pine
Tahoe City
Truckee
Healdsburg
Encinitas
Carmel-by-the-Sea
Sausalito
Capitola
Solvang