Tolchester Beach

Tolchester Beach is back. It’s not the same as in its Victorian heyday; instead you’ll find a happening Chesapeake Bay tiki bar and beach. This is where you go if you want cocktails, beach and music in one scene.

Address: 21085 Tolchester Beach Rd, Chestertown, MD 21620

Tolchester Beach is across the Chesapeake Bay from Baltimore on the Eastern Shore. It used to be a popular Victorian resort; boatloads of beachgoers would take a ferry to Tolchester.

Tolchester Beach (Photo courtesy Maryland Historical Society)

That died out when the Bay Bridge was built and people could drive to Atlantic shore beaches.

The area languished and became a marina with a little beach and a nice pool for boaters using the marina. But marina folk built it up in 2015-16 and created a summer beach party scene on a large sandy waterfront.

Shanty Beach Bar at Tolchester Beach, MD

This is a private beach owned by Tolchester Marina, so additional restrictions apply. The beach and bar are for marina slip holders, but they welcome day-trippers. There’s a parking with short walk to the beach area.

If you come by boat, teenage staff are on standby to help dock your boat for a few hours, or anchor near the beach and swim in.

Tolchester Beach has a full-service bar, called The Shanty, which typically has live music throughout the weekend with special concerts scheduled through the summer.