Top Cruising Destinations: The Historic And Charming Town Of Galesville, MD

Top Cruising Destinations

Located on the southwest fork of the West River, Galesville is only a two-hour sail from from Annapolis and offers scenic views and historic charm. 

While the West River is well marked throughout the day, some of the day marks remain unlit at night – making it tricky to navigate the river after dark. The channel snakes through a big S-turn but is wide enough that you can sail into the anchorage. It’s important that you pay attention to the marks, as missing one could mean grounding out in the mud! Visiting Galesville is best during the day when the river is easier to navigate and you can enjoy the beautiful scenery.

The tiny town of Galesville is rich in history and character, dating back to 1652 when a land grant was issued. It’s the perfect place to stop and to enjoy the scenic views and charm while grabbing a bite to eat.

Thursday’s Steak & Crab House

If you’re looking for a casual quick bite to eat, Thursday’s Steak & Crabhouse is your go to. It’s nestled right up on the water and offers stunning views from their covered deck.

You’ll find true Maryland dishes like crabs, crab cakes, and crab pretzels. Crab and Old Bay on everything, that’s how Maryland does!

This is the perfect spot for those who are just passing by and wanting to grab something quick and easy.

Pirate’s Cove

If you’re in the mood for fine classic and casual seafood dining, Pirate’s Cove is the place to be. Their casual waterfront atmosphere sets their visitors up for the most beautiful views of the West river.

Dine inside for a more formal affair or hang out on the deck for a casual experience. Happy hour at the bar is from 3-7 pm and offers an extensive small bites menu and drink specials.

Every Wednesday from April to September you can watch sailboat races starting at 6 PM. There’s dancing and live entertainment on Friday and Saturday nights, check out their calendar for a full music and events line up.

The Pirates Cove marina offers nightly boat slip rentals, fuel docks, pool availability, showers, and more. They even offer lodging if you’re looking to hop off the boat for the night.

Galesville offers such beautiful scenery that many people will anchor up and have a cook-out on their boats. East of Pirate’s Cove at the mouth of South Creek is the main anchorage where you will often see other boats. Another, more quiet anchorage can be found to the south in Smith Creek.

The quaint town of Galesville, MD is close enough to most of the major destinations around the Bay Bridge area, like Annapolis, Baltimore, and St. Michaels that it can be easy to overlook. It’s a beautiful area and surely something you don’t want to miss out on!

What’s your favorite thing to do in Galesville?