Chestertown, Maryland

Chestertown, Maryland​

Chestertown, Maryland is a town steeped in history. With a maritime and colonial heritage, you’ll feel the history as you walk along the beautiful brick roads and view the architecture that has been preserved from the town’s beginnings. But history isn’t the only thing that should bring you to Chestertown. You’ll feel right at home as you explore the popular Farmers’ Market or experience one of the town’s renowned festivals.


In order to fully explore this Maryland town, you’ll need to stay for more than just one day. You can find accommodation in the form of the well-known hotels of the Holiday Inn Express & Suites and Quality Suites, but they aren’t your only options. The Imperial Hotel is a popular tourist destination and locals flock to the Kitchen at the Imperial located within. If you want to experience more of the history Chestertown has to offer, however, you may want to book a room in one of the many bed and breakfasts in the area.


Whether you’re staying at the Imperial Hotel or not, the Kitchen is beloved by locals and tourists alike. If you’re looking to grab coffee or some light lunch, you may find yourself at Play It Again Sam’s, where you’re likely to run into local university students. With such a beautiful locale, why not eat with waterfront views? The 98 Cannon Riverfront Grille offers just that, along with mouthwatering seafood.


You’ll find all the shopping your heart could desire within the Historic District. High Street and Cross Street are lined with elegant boutiques, such as Twigs and Teacups or Cornucopia. Both are excellent places for buying gifts and souvenirs and have a wide array of products.

Things to Do

No matter when you’re visiting, you should walk along the Historic District. Located downtown, this district has great walking appeal and allows you to take in the sights. Whether you’re shopping or walking along the Chester River, there’s always something to do. The galleries and studios can be found downtown, mostly along the Historic District. If you’re visiting during the first Friday of the month, you may be in for a treat – the town holds “First Fridays”, where select galleries and stores extend their hours.

One of the draws of this quaint Maryland town is the amount of festivals that occur here. If you’re visiting around Memorial Weekend, take some time out to experience the Annual Tea Party Festival. In October, Chestertown is home to the Wild Fowl Festival, which you won’t experience anywhere else.