Sightseeing
You can take cruises on the Chester River aboard this 18th Century schooner. Great for kids, who also get to help hoist the sails. Remember to cover your ears though when they fire the cannon.
17 locals recommend
Sultana Education Foundation
200 S Cross StYou can take cruises on the Chester River aboard this 18th Century schooner. Great for kids, who also get to help hoist the sails. Remember to cover your ears though when they fire the cannon.
Food Scene
Great coffee, relaxed atmosphere, good light lunch menu - also pick up a bottle of wine.
25 locals recommend
Play It Again Sam
108 S Cross StGreat coffee, relaxed atmosphere, good light lunch menu - also pick up a bottle of wine.
Procolino's Pizza
711 Washington AveGreat pizza in a friendly environment.
Pull up by boat or take a short drive to this restaurant that looks directly out on the Chestertown Marina and the Chester River
23 locals recommend
Fish Whistle
100 George StreetPull up by boat or take a short drive to this restaurant that looks directly out on the Chestertown Marina and the Chester River
Best Chinese food in Chestertown. Usually no more than a 10-15 wait for take-out, or call ahead to have it waiting.
6 locals recommend
China House
2233 Eastern AveBest Chinese food in Chestertown. Usually no more than a 10-15 wait for take-out, or call ahead to have it waiting.
Arts & Culture
Small cinema which is usally pretty quiet. Cheap matinee tickets (before 5pm). Shows all the top releases. Great for a rainy day.
Chesapeake Movies
21 Washington SquareSmall cinema which is usally pretty quiet. Cheap matinee tickets (before 5pm). Shows all the top releases. Great for a rainy day.
Everything Else
Sacred Heart Catholic Church
508 High StCatholic Church
Christ Methodist Church
Methodist Church
Go to the Fountain Park on Saturday mornings for a great market of locally grown produce as well as arts and crafts.
Fountain Park
Go to the Fountain Park on Saturday mornings for a great market of locally grown produce as well as arts and crafts.
Essentials
ACME Markets
711 Washington AveGet all the groceries you need right here