Established as a colonial port of entry in 1706, Chestertown is situated along the banks of the Chester River. The historic waterfront town is a growing destination for the visual, performing, and literary arts.

Community Gateway to Campus

The Washington College Academy of Lifelong Learning is a popular way for community members to participate in classes and campus life. 
Our programming connects locals with students, faculty, and staff.


Festivals and Community Events

Chestertown holds a variety of large events and festivals throughout the year. In October check out the Sultana Foundation's Downrigging festival for a lovely weekend of tall ships, bluegrass, and fall weather. Are ships not really your thing? No worries, check out the Dickens of a Christmas Festival in December and take in the holiday spirit. If you are here for the summer be sure to check out the Tea Party Festival in May.

Chestertown Farmers Market

Every Saturday from 8am-12pm local vendors line High Street selling everything from fresh local grown produce to handmade art. Looking to grab breakfast while at the market? Look no further than local businesses like Evergrain Bread Co., or Play It Again Sam's .

Local Dining

Whatever you may be craving you can surely find it in Chestertown. With Evergrain Bread Co. perfect for a morning cup of coffee and a pastry, Procolino's for some of the best pizza in town, and Café Sado for all the sushi lovers. If you are looking for a sweet treat there is no shortage of options in Chestertown with everything from handmade chocolate at Bespoke Chocolate, to delicious ice cream from places like Stam's Luncheonette, or the newly opened Sugardoodles. Just be sure to check the hours before you go..

What's going on out of town?

If you are up for an adventure there are plenty of places surrounding Chestertown to checkout. Rock Hall is perfect for music lovers with The Mainstay being a great place to catch a band or an open mic. If you want to soak up the sun and enjoy the nice weather then hop on over to Betterton and enjoy their lovely beach. Missing some dorm essentials? Head on over to head north to Middletown, DE and enjoy tax free shopping.


Located off the beautiful Chester River, Chestertown has an abundance of nature. While the town is known for its riverfront, the trees are something that often get overlooked. Chestertown has been certified by the Arbor Day Foundation as Tree City for 40+ years. With Washington College's Campus being itself an Arboretum. Just off the North Commons of campus there is an entrance to Chestertown's Rail Trail, which is perfect for a walk or bike ride downtown or to the waterfront.