Great Small Towns Near Washington, DC

Admit it—you often dream of a simpler life. A small-town life. Here are 27 places that will charm you with old-fashioned hospitality and new fangled vigor, whether you visit for a day, a weekend—or for good.

America’s “Coolest Small Town”

Berlin, Maryland

Explore Love & War

Boonsboro, Maryland

Kayak a Wildlife Refuge

Cambridge, Maryland

Enjoy a Halloween Tradition

Chadds Ford, Pennsylvania

Party Like It’s 1774

Chestertown, Maryland

Go Wild On the Shore

Chincoteague, Virginia

Attend the Big Game

Cumberland, Maryland

Tour Quirky Museums

Doylestown, Pennsylvania

Eat Finger-Lickin’ Food

Easton, Maryland

Listen to Toe-Tapping Bluegrass

Floyd, Virginia

See Frank Underwood’s “Hometown”

Havre de Grace, Maryland

Hunt for Great Antiques

Kilmarnock, Virginia

Savor the Beach in the Off-Season

Lewes, Delaware

Dig Into Real Farm-to-Table Dining

Lewisburg, West Virginia

Feel Smart in A College Town

Lexington, Virginia

Have a Drink With a Polar Bear

Ligonier, Pennsylvania

See a Grand Christmas Parade

Middleburg, Virginia

Thinking of Moving to a Small Town? Read This First.

Millwood, Virginia

Tour Historic Homes

New Castle, Delaware

Check Out the Next St. Michaels

Onancock, Virginia

The Smallest of the Small

Port Tobacco, Maryland

Bike, Then Beer-Taste

Purcellville, Virginia

Pedal & Paddle Through History

Shepherdstown, West Virginia

Shopping Mecca

St. Michaels, Maryland

Watch Shakespeare

Staunton, Virginia

Immerse Yourself in Colonial Charm

Waterford, Virginia

Stroll a Vibrant New Downtown

Winchester, Virginia

Contributing to this section were Sherri Dalphonse, Jennifer Barger, Eleanor Berman, Jayne Clark, Kristina Henry, Melanie D.G. Kaplan, Dale Leatherman, Andrea Poe, Douglas Rogers, Lynn Seldon, Renee Sklarew, Candyce Stapen, and Joe Sugarman.

This feature appears in our August 2015 issue of Washingtonian.