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Best destination town on the eastern shore of the Chesapeake Bay?

Following "guyacrossthehall" and "jck" recommendations, if you travel through MD Eastern Shore via Rt. 213 (very picturesque drive - I may add), you may want to check out the historic town of Cheasapeake City, MD

The town is divided in half by the C&D canal (although most of the town is on the south side of the canal). There are shops, B&Bs, and restaurants right on the waterfront, all in historic buildings. There is even a boat dock for people who want to visit the town via water access.

My husband and I like to eat at The Bayard House which also happens to be the oldest building in the town (dating from 1780) . If you ask to eat outside on the patio/porch you can enjoy the meal while you watch the boats go by.
Sometimes me and my husband go to the Tiki Bar at the Cheasapeake Inn ( for a drink and to people/boat watch and they also feature live music, but it can get a little crowded sometimes.

I live approx. 6 miles from Cheasapeake City off Rt. 213 and the town is definitly worth a stop and see. As an added bonus - although keep in mind the town will be crowded/parking challenges-
JUNE 27 is CANAL DAY which is a once year town festival.
Enjoy - puffbunnies

Jun 20, 2009
puffbunnies in Mid-Atlantic