Chestertown, Maryland
Journey to the Eastern Shore of Maryland

Chestertown, Maryland

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Located on the Eastern Shore of Maryland's Chesapeake Bay and founded in 1706, Chestertown is one of the most historic and beautiful locations in the state. It is home to many small businesses and colonial buildings. Hunting and fishing are a large part of the culture there.

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Check out the local Wildlife

(and kill them!)

Chestertown is home to a many types of wildlife, several of which are popular for hunting. Popular species for hunting are the local deer, geese, and ducks.

More about the local wildlife
Downtown Chestertown homes

Beautiful Colonial Homes and the Imperial Hotel

There are several options for lodging on on the Eastern Shore. Chestertown is home to the historic Imperial Hotel, where you can find delicious food and drinks as well as a comfortable bed. Many homeowners in Chestertown offer up their homes on the popular website Airbnb, some of which are historic Chestertown buildings.

Downtown Chestertown homes

Local Shops and Delicious Food

Chestertown is home to many small shops, bars, and cafes. When I say "many" I actually mean very few. Although there aren't very many, they all have tons of personality and high quality offerings. You can find some great coffee roasted locally (Annapolis) and a good selection of Maryland beers. Pastries at the Evergrain Bread Company are not to be missed.

Pack for the Season

If you plan on visiting Chestertown, you should pack according to the season. Chestertown gets extremes on both ends of the spectrum, from hot and humid summers to freezing winters with several feet of snow.