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

Tall Ships
Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival
Image Credit: Town of Chestertown
Chester River Packet Company
Chester River Packet Company
Image Credit: Chester River Packet Company

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 Fountain in the Town Square

1 Chestertown Arts & Entertainment District

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 Image Credit: 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 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.
More info....

Arlo the Dog Image Credit: Jim Meyer

3 Dog Friendly

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.
More info....

Antique books

4 The Historical Society of Kent County

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


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Washington College Image Credit: Washington College

5 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...

Tall Ships Image Credit: Town of Chestertown

6 Schooner Sultana

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. 


More about Sultana Education Foundation


Type:
Attraction


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


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vintage finds Image Credit: Crumpton's Auction

7 Dixion's Crumpton 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.

  


More about Dixion's Crumpton Auction


Type:
Attraction


Location:
2017 Dudley Corners Rd
Crumpton, MD 21628
410-928-3006


Learn More
Maryland crabs and corn

8 Eat & Drink

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 .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.
Check out all of the fantastic dining options in and around Chestertown here.

Featured Places
Old house exterior
01
Location:
301 High St
Chestertown, MD 21620
Large ship
02
Location:
200 S. Cross St
Chestertown, MD 21620
Dixion's Crumpton Auction sales
03
Location:
2017 Dudley Corners Rd
Crumpton, MD 21628
bad alfreds logo
04
Location:
323 High Street
Chestertown, MD 21620
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