Welcome to St Michaels & Tilghman Island
The prettiest little village on the Eastern Shore, St Michaels lives up to its motto as the 'Heart and Soul of Chesapeake Bay.' Hugging US 33, it's a mix of old Victorian homes, quaint B&Bs, boutique shops and working docks, where escape artists from Washington mix with salty-dog watermen. During the War of 1812, inhabitants rigged up lanterns in a nearby forest and blacked out the town. British naval gunners shelled the trees, allowing St Michaels to escape destruction. The building now known as the Cannonball House was the only structure to have been hit.
At the end of the road at the end of the peninsula, and over the US 33 drawbridge, tiny Tilghman Island still runs a working waterfront, where local captains take visitors out on graceful sailing vessels.