
Outside diners at the Pirate Cove enjoy views of all the sailboats and the West River with their drinks or their meal.
An occasional series of bars, taverns, saloons, watering holes of note — not that we’re advocating tipsiness, of course.
It was one of those August days when you have to celebrate summer: cooler than usual, sky blue as the Caribbean, breeze soft as a kiss. And then there’s that feeling that there won’t be many more of these before fall.
It was a perfect day to hang out on the waterfront. But not at the Inner Harbor or Annapolis this time. We headed to Galesville on the West River, to the Pirate’s Cove. Even though I felt like I was really getting away from it all, it’s got its followers. This is no new discovery for sailors and local imbibers. It’s been serving food and drink since 1960.
It’s where the locals gather for Wednesday night sailboat races and for dancing and live music on the weekends.
We stopped for a beer and a crabcake one summer afternoon. And I got just what I expect from a traditional waterfront restaurant in Maryland. The waitress was uber-friendly with lots of opinions. The crab cake golden brown with the right amount of lump crab and a balance of creaminess and spice. The beer was cold. The company kept me laughing.
Pirate’s Cove is south of Annapolis, off Route 2 and easy to find. Besides lunch and dinner Monday through Saturday, they offer Sunday brunch and dinner and the bar is open Friday and Saturday until midnight.

Through this portal, you’ll find Big Mary’s Dock Bar with all the views and appetizers you could wish for.
Big Mary’s Dock Bar is adjacent to the restaurant with its own bar menu from appetizers to sandwiches to pizza. If you have to have local beer, you’re in luck. They keep Heavy Seas on draft along with all the national favorites. A lively entertainment schedule keeps the place humming.
After a leisurely lunch, a stroll past all those gorgeous sailboats and a moment to inhale West River’s fresh air, we were ready for whatever the rest of the day had in store.
© Text and photos Mary K. Tilghman
Previous Tipsy Tourist posts:
- Abbey Burger Bistro in Ocean City,
- Boordy Vineyards and
- The Wine Bin in Ellicott City.
If you have a favorite spot you’d like to see here on Thirsty Thursday, let me know.
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