Chestertown, MD

Before we were invited to spend the weekend at our friend’s house in Chestertown, Maryland, I hadn’t heard of the town. It’s not very easy to get to from Washington, DC. It’s on the other side of the Bay Bridge, which I have always associated with traffic jams. Despite this physical and psychological barrier to the serene Eastern Shore, my fianc√© and I made the trip on a Saturday morning and spent about 36 hours there, and only have good things to say about the place.

Water Street, Chestertown Maryland

Water Street, Chestertown

Chestertown is a quaint and beautiful town, but it’s not a party-town or anything; in fact, I think retirees make up a large portion of the population.¬† No knock against our host being a retiree, too–he’s awesome and can totally hang out with the younger crowd.

Chestertown Maryland

Downtown Chestertown Maryland

Chestertown reminded me a lot of New Castle, Delaware, which is only about an hour away. You can read my New Castle post here. Chestertown has a nice main street called High Street that is lined with shops, cafes, and restaurants. There are nice cobble stoned side streets and the park area around Kent County Courthouse is covered with old trees and bordered by a row of carriage houses that have since been turned into law offices. Whether those law offices are still in existence, I’m not sure. The town is second in Maryland only to Annapolis in the number of 18th century buildings in its city limits.

Chestertown Maryland

Chester River

Though we spent a lot of our time relaxing at our guest’s house, we also tried out some of the local establishments. We had lunch the first day at a tavern a bit outside of the main historic district called Brooks Tavern, which had great food and a menu with more than just the usual staples you’d expect in a tavern. On Saturday night, we ate al fresco at the The Lemon Leaf Cafe. We five, and my dog Ollie, sat out on the wide sidewalk and ate pizza under a clear night sky while unseen crickets chirped their summer night soundtrack. I liked the food so much that I went back about 9 hours later to the same restaurant for breakfast.

Reenactors for the Battle of Caulk's Field, War of 1812,

Reenactors for the Battle of Caulk’s Field, War of 1812,

For my coffee fix, I went to a cafe called Play It Again Sam, off High Street. I thought the coffee was top notch and the breakfast sandwiches filling and cheap. I also liked the cozy interior and the ample seating in the front. The servers behind the counter were all really friendly and seemed to be enjoying what they were doing.

Chestertown Maryland

You might be wondering what those reenactors in the above picture are doing. We happened to visit the town on the day of the annual reenactment of the War of 1812 Battle of Caulk’s Field. Ollie seemed to really want to know what was going on:

Chestertown Maryland

Who are these guys?

The ride out to Chestertown is nice, despite the Bay Bridge obstacle. If you can stay there overnight it will make the drive even more worth it.


  • Brooks Tavern: Great food, fresh-looking decor inside; it’s a little outside of the downtown core–probably better to drive.The Lemon Leaf Cafe: See if you can eat at one of the tables on the sidewalk if it’s a nice day/night.
  • Play It Again Sam: Try their bacon egg and cheese sandwiches


Kevin is based in Washington, DC and writes about his travel adventures in the Mid-Atlantic region and around the world. Through entertaining writing and eye-catching photography, he aims to provide readers with useful information as they plan their next trips.

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