Eastern Shore Towns and Chesapeake Bay Views
Begin your day with a pick-up from your hotel or lodging in Annapolis or the surrounding area. Drive across the iconic Chesapeake Bay Bridge and enjoy panoramic views of the bay. Stop briefly on Kent Island for coffee, a snack, and a scenic photo opportunity of the bridge and waterfront.
Continue the journey to Chestertown, one of Maryland's most important colonial cities and home to Washington College. Walk through the historic streets, admire the preserved Georgian architecture, and soak in the charm of this waterfront town.
After exploring Chestertown, select two of the following destinations to tailor your Eastern Shore adventure:
Historic Easton - Stroll through this vibrant town filled with galleries, shops, and historic landmarks.
Cambridge - Visit the Harriet Tubman Museum (currently under repair as of August 2025, but the surrounding town and history remain inspiring).
Oxford - Experience Maryland's seafood culture by dining on fresh crabs or oysters in a picturesque setting by the water.
St. Michaels - Wander through this charming harbor town, explore boutique shops, and enjoy views of the Chesapeake Bay Maritime Museum and waterfront.
End the day with a comfortable drive back across the Chesapeake Bay Bridge, returning to your hotel or lodging in the evening with lasting memories of Maryland's Eastern Shore.
