Location: Leonardtown
Top Things to do in Leonardtown
Countries
What to do and see in Leonardtown, Maryland (MD): The Best Free Things to do
Leonardtown is a town in and the county seat of St. Mary's County, Maryland, United States. The population was 2,930 at the 2010 census. Leonardtown is perhaps most famous for the national oyster-shucking championship that occurs annually at the St. Mary's County fairgrounds.
Restaurants in Leonardtown
1. North End Gallery
Overall Ratings
5.0 based on 10 reviews
2. Port of Leonardtown Winery
Overall Ratings
4.5 based on 70 reviews
Port of Leonardtown Winery consists of twelve vineyards from St Marys, Calvert, Charles, & Kent counties in Maryland.
Reviewed By theVirgdoe - Waldorf, United States
Love the friendly staff and our door seating area. I love coming and sitting outside with some friends or under the covered and heated sun room when it’s cold.
3. Olde Town Pub
Overall Ratings
4.5 based on 10 reviews
The Olde Town Pub offers an upscale dining and drinking experience in the heart of downtown Leonardtown, Maryland. We feature 14 beers on tap as well as award-winning chicken wings along with several popular appetizers and main courses. When you think of Leonardtown restaurants, think of the Olde Town Pub.
4. Leonardtown Wharf Park
Overall Ratings
4.5 based on 17 reviews
Reviewed By hulahoopgo - Leonardtown, United States
This is a very nice, calm place to paddle around. It’s inexpensive to rent a kayak or paddleboard for a few hours from PAC Paddle Sports. There is a kayak launch which makes it easy to get in and out of the water and the PAC paddle employees help you. You can paddle up McIntosh Run and see a lot of birds. There is a little building at the wharf where you can buy snacks, ice cream treats, and drinks. They also keep the bathroom clean. It’s a very nice experience. We’ll be going back.
5. The Old Jail Museum
Overall Ratings
4.0 based on 11 reviews
Built in 1876 and in use until 1945 by the oldest sheriff’s office in the nation, this granite block and brick structure retains its original upstairs cells where prisoners were once segregated by gender and race. The jail keeper's quarters downstairs house related artifacts.
