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.
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.
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.