Historic Chestertown, Maryland

Rob
Historic Chestertown, Maryland

Food scene

great food on the water. they had a fire over the winter so they are serving under a tent but it is great food
9 locals recommend
98 Cannon Riverfront Grille
98 Cannon St
9 locals recommend
great food on the water. they had a fire over the winter so they are serving under a tent but it is great food
Great food in a really pretty place.
13 locals recommend
Watershed Chestertown
337 High Street
13 locals recommend
Great food in a really pretty place.
Really great food in a historic hotel on High Street. Great bar greets you as you enter and great food awaits.
20 locals recommend
The Kitchen at the Imperial
208 High St
20 locals recommend
Really great food in a historic hotel on High Street. Great bar greets you as you enter and great food awaits.
Great pizza menu cooked to order, they make their own booze onsite and offer things like broiled chicken wings and crab dip
13 locals recommend
BAD Alfred's Distilling
323 High St
13 locals recommend
Great pizza menu cooked to order, they make their own booze onsite and offer things like broiled chicken wings and crab dip
really good sandwiches/ hoagies/ subs with a solid assortment of beer, seltzers and hard liquor
Jj's Deli & Liquors llc
511 Washington Ave
really good sandwiches/ hoagies/ subs with a solid assortment of beer, seltzers and hard liquor

Neighborhoods

Chestertown was a royal port for the British so there are beautiful historic homes in the downtown/ historic district. There are maps that help you learn about the homes and their famous/ important residents from history.
31 locals recommend
Chestertown
31 locals recommend
Chestertown was a royal port for the British so there are beautiful historic homes in the downtown/ historic district. There are maps that help you learn about the homes and their famous/ important residents from history.

City advice

Getting around

Travel time from Phila or DC

From the Main Line it is about 85 miles to Chestertown, plan on traffic where 95 meets Route 1 at Christiana Mall. Once you get over the new bridge there is very little traffic to speak of getting to town. From DC you have the same amount of mileage with the added joy of the Bay Bridge.....