Tall Ships
Town of Chestertown

Top Things to See and Do in Chestertown

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

Tall Ships
Town of Chestertown

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 Arts & Entertainment District
Chestertown Fountain in the Town Square

Explore Chestertown's Main Street and Arts & Entertainment District and discover a town in which arts and cultural thrive.

Annual Festivals and Events
reenactors on ship
Chestertown Tea Party Festival

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 Chestertown's "Music in the Park" Summer Concert Series - but no matter what time of year you visit, you can count on an entertaining event or festival.

Dog Friendly
Arlo the Dog
Jim Meyer

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

The Historical Society of Kent County
Antique books

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.

Washington College
Washington College
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.

Schooner Sultana
Tall Ships
Town of Chestertown

On board the Sultana,  people connect to the Chesapeake Bay’s history, ecology, and culture, and become inspired 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. 

Dixon's Crumpton Auction
vintage finds
Crumpton's Auction

Crumpton's is a third generation auction company established in 1961 by Norman Dixon where everythng moves at a fast pace. With seven auctioneers on staff  it is not unusual for Crumpton's to conduct three to four auctions simultaneously resulting an average of 200 items sold per hour or 3,000 to 6,000 lots a week. You  never know what you may discover at Crumpton's whirlwind of vintage treasures.


Eat & Drink
Maryland crabs and corn

Chestertown  is a magnet for traveling foodies. Known for its wealth of Chesapeake Bay cusine, Chestertown is located on the Upper Eastern Shore Section of the Maryland Crab & Oyster Trail (Needs Link) .Visiting the Chestertown Farmers and Artisans Market (opens at 8am every Saturday, year-round) is a great way to aquait yourself with the local farmers and artisans. One of the newer additions to Chestertown's food repertoire is Figg's Ordinary, an entirely gluten-free cafe. For something a little stronger head to  Bad Alfred’s is a brewpub and distillery featuring house-made spirits, local craft beer and wood-fired pizzas.