Tolchester Beach is a popular Chesapeake Bay tiki bar and swimming beach. This is where you go if you want beach, cocktails, and music in one scene. It’s easy to reach by boat, but a bit of a drive by car. 

Address: 21085 Tolchester Beach Rd, Chestertown, MD

What’s At Tolchester Beach?


  • Private Beach
  • Available for Marina, Restaurant & Tiki Bar Guests
  • Outdoor Restaurant Seating on the Beach
  • Music on the Weekends in Summer Season

Tolchester Beach on the Chesapeake Bay’s Eastern Shore across from Baltimore used to be a town. It was a Victorian beach resort overlooking the Chesapeake Bay, catering to visitors from Baltimore wanting to escape the city heat.

The roller coaster and merry-go-round are long gone, and so is the town. Tolchester Marina is there now. In 2018 they built a big tiki bar, a “grill” restaurant, a music venue and stretched out their little used beach. Now it’s a summer hot spot.

Tochester Beach

Is Tolchester Beach Open to the Public?

Tochester Beach

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.

Boats anchor near the swimming line on hot summer days, and passengers jump in to swim about or head to the bar/restaurant. The beach is also open to restaurant and tiki bar guests who come by car.

The full-service tiki bar is called The Shanty and typically has live music throughout the weekend with special concerts scheduled through the summer.

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

It’s not easy to get to by car, but it’s a nice drive through farmland for the adventurous. There are no major towns nearby and if you come from the city it feels like the middle of nowhere.

The parking lot is behind the full-service marina, about a five-minute walk to the beach area. Follow the signs. 

Tolchester Marina also has private events through the year and sections may be closed off for a wedding or another such event.

Tolchester Marina