Chestertown Travel Guide
  • Photo: Jon Bilous / Shutterstock

Chestertown

Second only to Annapolis in its concentration of 18th-century houses, Chestertown was a major international port in Colonial days: a tall, brick customhouse continues to dominate the High Street waterfront. Still the home of families whose local roots go back many generations, the town has its share of newer residents, many of them retirees. Today inns and good restaurants, fine-art galleries, three independent bookstores, and antiques shops line the brick pavements of High Street, Chestertown's broad, tree-lined main street. To walk along its narrow streets, some of them cobbled, is to commune quietly with some of the country's earliest history. At the northern edge of Chestertown is Washington College, one of the nation's oldest liberal-arts institutions. George Washington helped found the college in 1782 through a gift of 50 guineas.

Advertisement

Book A Trip
  • HOTELS

  • FLIGHTS

  • PACKAGES

  • CARS

Trip Finder

Plan Your Next Trip

Subscribe to Newsletter
Sign up for Travel Tips & News
I want emails from Fodor's Travel with travel information and promotions. I can unsubscribe any time using the unsubscribe link at the end of all emails.

Thank you for your interest!

Look out for our newsletters with travel tips and special offers.