Top Things to See and Do in Chestertown

Stroll historic tree-lined streets, and explore the natural beauty of the Chester River

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Featured Places

couple taking selfie
Photo By: Clark Vandergrift
Tall Ships
Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival
Photo By: Town of Chestertown
Chestertown Historic District Marker
Photo By: Clark Vandergrift

Founded in 1706,  Chestertown is a historic college town along the banks of the Chester River on Maryland's Eastern Shore. The brick sidewalks lined with shops, restaurants and inns welcome visitors to meander and browse. A visit to Chestertown's Historic District to admire the fine colonial residences is a must!.

Chestertown A&E District

1 Arts

Explore Chestertown's Main Street and Arts & Entertainment District and discover a town inwhich arts and cultural thrive.
Check out this map of galleries, restaurants and shops.

reenactors on ship Photo By: Chestertown Tea Party Festival

2 Annual Festivals and Events

Experience Chestertown like a local by attending one of the many unique annual events. During Memorial Day weekend there is the annual Chestertown Tea Party Festival and don't miss the Pirates and Wenches Fantasy Weekend in August - but no matter what time of year you visit, you can count on an entertaining event or festival.
More info....

Garfield Center Marquis in Chestertown Photo By: Clark Vandergrift

3 The Garfield Center for the Arts at the Prince Theatre

The Garfield shakes-up the cultural life of Chestertown with great programming that nurtures and celebrates arts and artists - essential elements of life in Chestertown.
More info...

dog at Crow Vinyard Photo By: Clark Vandergrift

4 Dog Friendly

Chestertown is the perfect place for your furry friend to wag its tail and enjoy the refreshing breeze of this waterside community. The Kent County area has plenty of pet-friendly businesses for them to explore and Chestertown its very-own dog park.
More info....

Antique books

5 History

Serving as Kent County's seat of government since 1706, Chestertown has been a Royal Point of Entry, the scene of its own Revolutionary Tea Party in 1774, and the hub of a bustling agricultural and seafood region. The Historical Society of Kent County is a treasure trove of history and offers a great self-guided walking tour you can access via your smartphone.


More about Historical Society of Kent County


Type:
Attraction


Location:
301 High St
Chestertown, MD 21620
410-778-3499


Learn More
Washington College Photo By: Washington College

6 Washington College

Founded in 1782, Washington College was the first college chartered in the sovereign United States of America. General George Washington lent his name, donated 50 guineas to the founding, and served on the first Board. The mission back then was to cultivate responsible citizen-leaders. Nowadays, the focus is on giving students the chance to succeed on their own terms.
More info...

Visit Maryland

7 Scooner Sultana

The Sultana connects people to the Chesapeake Bay’s history, ecology, and culture, inspiring all to be a part of  preserving and restoring America’s largest estuary.

Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival has evolved into one of the largest annual Tall Ship gatherings on the East Coast. 


More about Sultana Education Foundation


Type:
Attraction


Location:
200 S. Cross St
Chestertown, MD 21620
410-778-5954


Learn More
Featured Places
Old house exterior
01
Location:
301 High St
Chestertown, MD 21620
Large ship
02
Location:
200 S. Cross St
Chestertown, MD 21620
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