8 Free Things to do in Chestertown That You Shouldn't Miss

April 27, 2022 Kiesha Cripe

With a colonial history dating back to the 17th century, Chestertown, Maryland is proud of its maritime heritage. Sitting on the banks of the Chester River, sailing ships can still be seen coming into port. The city is the home of the Schooner Sultana, an exact replica of an 18th century ship that served in the British Royal Navy, now operating as an educational vessel. Every Memorial Day, the city hosts The Chestertown Tea Party Festival, proudly tossing the British overboard annually.
Restaurants in Chestertown

1. Book Plate

112 S Cross St, Chestertown, MD 21620-1549 +1 410-778-4167 http://www.bookplate.biz/
Excellent
90%
Good
6%
Satisfactory
0%
Poor
0%
Terrible
4%
Overall Ratings

5.0 based on 31 reviews

Book Plate

Reviewed By TJTT - Washington DC, United States

Book lovers can spend hours in this wonderful used bookstore. Very well curated with a wealth of books in all categories. Friendly and helpful staff, including Tom the owner. Don't miss this gem if you are in Chestertown.

2. Chester River Wine & Cheese Co.

117 S Cross St, Chestertown, MD 21620-1513 +1 443-282-0220 [email protected] http://www.chesterrivergourmet.com/
Excellent
93%
Good
7%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 27 reviews

Chester River Wine & Cheese Co.

Located in historic Chestertown on the Maryland Eastern Shore, Chester River Wine & Cheese Co. is a specialty food market offering international and domestic wine, cut-to-order cheese, charcuterie and cured meats, as well as gourmet foods such as handmade jam, mustard, salts and sweets, pasta and specialty sauces, local beef, specialty sausage, olive oils and vinegars. Case discounts are available. In addition to our retail offerings, we also provide onsite table service of select wine, cheese, and desserts in our informal gourmet shop atmosphere. Our menu changes the first Friday of every month. Every cheese board includes bread from our local bakery, chutney and mustard, dried fruit and nuts. We have tables inside and out and are fully wheelchair accessible. Families are welcome. Seating is limited; groups of 6 or more are encouraged to call us to ensure availability. Our table service begins at 11:30 and cheese board service ends at 3::15 (Sun & Mon) and 6:15 pm (Tue - Sat); wine and dessert is served until 3:30 (Sun & Mon) and 6:30 pm (Tue - Sat). Our retail shop is open until 7 p.m.

3. Twigs & Teacups

111 S Cross St, Chestertown, MD 21620-1558 +1 410-778-1708 [email protected] https://www.facebook.com/TwigsTeacups/
Excellent
83%
Good
17%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 12 reviews

Twigs & Teacups

Gifts and more On the Eastern Shore.

4. Historical Society of Kent County

301 High St Bordley History Center, Chestertown, MD 21620-1333 +1 410-778-3499 [email protected] http://www.kentcountyhistory.org
Excellent
56%
Good
38%
Satisfactory
6%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 16 reviews

Historical Society of Kent County

The Historical Society of Kent County, Maryland, is a non-profit organization dedicated to the collection and preservation of artifacts, documents, and information that aid in the interpretation of all aspects of Kent County’s history. The Society shares this information through its research library, museum space, programs, publications and website in order to foster a knowledge and understanding of the shared heritage of the community. The Society supports and encourages the preservation of historic buildings and sites throughout Kent County.

Reviewed By PaleoGypsy - Philadelphia, United States

This is a worthwhile stop if you are seeking information about the area. The person is very helpful. A lot of print materials are available upon your request. As this area is rich in history, take the time to stop in and learn a few things about the area.

203 High St, Chestertown, MD 21620-1579 +1 410-778-7330 [email protected] http://www.massoniart.com/
Excellent
78%
Good
19%
Satisfactory
0%
Poor
0%
Terrible
3%
Overall Ratings

4.5 based on 27 reviews

MassoniArt Gallery

Respected by artists & collectors throughout the Mid-Atlantic region for over 30 years. For over 30 years, the Carla Massoni Gallery has worked in collaboration with architects, developers, interior design firms, art consultants, and non-profit organizations to bring art to the workplace. We have been honored to work with the US State Department’s Art in Embassies Program placing our artists work in American embassies throughout the world. We have placed works of art in SoHo lofts, New Jersey pharmaceutical companies, Delaware corporations, Baltimore non-profits, and Washington, DC law firms and associations. We provide a conduit for artists to interact with the business community by arranging opportunities for their work to appear in journals, newsletters and national publications.

6. River Arts Chestertown

315 High St Suite 106, Chestertown, MD 21620-1326 +1 410-778-6300 [email protected] http://chestertownriverarts.org/
Excellent
53%
Good
32%
Satisfactory
5%
Poor
5%
Terrible
5%
Overall Ratings

4.0 based on 19 reviews

River Arts Chestertown

RiverArts Mission: To engage our community in the creation, appreciation, and support of the arts through education, events, and exhibitions. RiverArts Vision: To inspire and foster creativity as a positive and sustainable force that enriches our community and establishes the region as a premier arts destination.

7. jellyfish joel's

22170 Great Oak Landing Rd, Chestertown, MD 21620-4101 +1 410-778-5007 http://www.facebook.com/pages/Jellyfish-Joels/114143571931781
Excellent
27%
Good
45%
Satisfactory
18%
Poor
0%
Terrible
10%
Overall Ratings

4.0 based on 11 reviews

jellyfish joel's

Reviewed By 839hcj

Jellyfish Joel's Review Great place to spend the day. Picnic tables galore. Food Truck right on the beach for tasty food. Exciting up close view of yachts passing through the Fairlee Creek inlet. Free golf cart transportation. HC Jones

8. Kent County Visitors Center

122 N Cross St, Chestertown, MD 21620-1547 +1 410-778-9737 [email protected] http://townofchestertown.com/visitors-2/kent-county-tourism-development/
Excellent
38%
Good
46%
Satisfactory
0%
Poor
8%
Terrible
8%
Overall Ratings

4.0 based on 13 reviews

Reviewed By PaleoGypsy - Philadelphia, United States

This is a good stop if you are seeking some basic information about the area. Brochures about events and attractions are available. There is a small area devoted to a gift shop. A tip jar is located on the desk. This place is located on High Street.

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