St. Michaels

St. Michael's is the oldest town in Talbot County, dating back to the mid-1600s. It is known as the "town that fooled the British." As one of my favorite small towns, it has a lot to offer in a day or weekend trip.

What To Do

Walk Around the Town

We enjoy walking around the town and local neighborhoods. Siting the historic homes takes you back in time.

Wineries & Breweries

St. Michael's Winery

St. Michael’s Winery has sweet and dry wines. Out of the sweets, we all loved the Gollywobbler Peach and the Chocolate Zin. Our dry wine favorite was the Malbec.

Eastern Shore Brewing

Eastern Shore Brewing has flights of beer. My favorite was the amber ale.

Chesapeake Bay Maritime Museum

This Maritime Museum is extremely well-done, showcasing the history and culture of the Chesapeake Bay. I recommend taking a tour, and then going into the very nice gift shop. The museum is a highlight of visiting St. Michaels.

Adventuring

You can also rent paddle-boards and kayaks from Shore Pedal and Paddle.

Where To Eat

Corah's Corner

At Corah’s Corner, a friend is one of the chefs. We each had a delicious meal and I loved my strawberry lemonade drink.

Justine's

Check out Justine’s for ice cream, which has a massive wonky selection of milkshakes and a wall where they spotlight people who finish the Titanic.

Foxy's

Foxy’s is right on the water and has an extensive drink menu and really good food.