37 Most Charming Towns in America

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

Most Charming Towns in America Places

• 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.

• Gatlinburg

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

• Monterey

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

• 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.

• 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.

• 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