Civil War Trails: Chestertown, Maryland

Looking for a nice weekend getaway with a side of history? Let us recommend a visit to Chestertown. Take a long walk along the tree lined streets and soak up the impressive collection of period buildings that Chestertown boasts.

There are three Trails’ signs downtown to help you find your way. We recommend starting your visit to town at Memorial Plaza, at 101 Park Row in Chestertown. The Trails sign here tells the story of the town coming to terms with memory, and correcting an omission more than 80 years in the making. From here go just around the corner to Lawyer’s Row on Court Street. The Trails sign is located on the grounds of the courthouse, and explores the wartime trajectory of a young lawyer, who cut his teeth here.

Once you have explored the architectural wealth that is Lawyer’s row, we recommend traveling across town toward the Sumner Hall GAR Post, with one important stop along the way. Bring your appetite along with you to The Kitchen at the Imperial, located on High Street. This restaurant is not only in one of the most distinct historic structures in town, circa 1903, it is also our team’s favorite restaurant in the area. Once you have gotten your fill of excellent local cuisine it is time to visit the last Trails site in town, one that is well worth saving for last.

The Sumner GAR Hall in Chestertown is one of only two remaining African American Grand Army of the Republic halls left in existence, and the only one still being used as a community space. Our visit was definitely the highlight of our time spent in town, and we think it could be yours as well.

Looking for more information? Keep an eye out for America’s Civil War Magazine’s March 2019 edition for a bigger write up of the region.

Let us help you travel like a local. Take a look at our maps, and don’t hesitate to ask for our recommendations for good eats, drinks, and lesser known spots along the way. Follow #civilwartrails and create some history of your own.