6 Things to Do in Chestertown That You Shouldn't Miss

September 20, 2017 Phylicia Berquist

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

203 High St, Chestertown, MD 21620-1579 +1 410-778-7330
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4.5 based on 22 reviews

Carla Massoni Gallery

Reviewed By Michael A - New Hope, Pennsylvania

We stopped in while in town over the Thanksgiving holiday. Beautiful gallery, very personal. The art was varied in terms of style and medium, but every piece was engaging. The owner was there, and took the time to explain some of the pieces.

2. Historical Society of Kent County

101 Church Aly, Chestertown, MD 21620-1505 +1 410-778-3499
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4.5 based on 13 reviews

Historical Society of Kent County

Visit the Geddes-Piper House, a beautiful 1783 merchant's home that provides an overview of Kent Co history from first settlement to the 20th century. Period furniture, porcelain and textiles offer the perfect backdrop for the story of the region, conveyed through interpretive signage. Our Genealogy & Local History Library contains a full collection of maps, cemetery records and reference books.

Reviewed By hllangford - Perry, Florida

I am partial because I am a Eastern Shore Maryland girl now living in Florida for almost 16 years but I just love Chestertown Historical Downtown. I never appreciated when I was a child but now when I return I am in awe of just how beautiful it all is!!

3. Garfield Center for the Arts at the Prince Theatre

210 High St, Chestertown, MD 21620-1518 +1 410-810-2060
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5 based on 7 reviews

Garfield Center for the Arts at the Prince Theatre

Since its inception in 2002, the Prince Theatre Foundation has enjoyed success in various community endeavors: - Producing top of the line theatrical and musical productions - Providing quality educational, enriching experiences in the arts for children and adults - Partnering with over a dozen community organizations Recognized and valued as a unique community center for the arts.

Reviewed By Avalonavalon - Mystic, Connecticut

Sylvia is a play not to be missed. The performers were superb. Will Robinson played Greg, Christine Kinloch played Sylvia, Jennifer Kafka Smith played Kate,and multi talented Brian Betley played Tom, Phyllis, and Leslie.
We were visiting on our boat to this charming town of Chestertown and noticed the play was being performed. We got tickets and are so glad we did.
Bonnie Hill did a wonderful job directing this fun play.

4. Art on High

200 High St, Chestertown, MD 21620-1586 +1 443-282-0134
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5 based on 2 reviews

Art on High

The Gallery at Rock Hall is a Contemporary and Modern collection of artists from near and far. We have a small collector's corner for those who search for the obscure yet valuable. Our eclectic collection is hand picked and curated with passion and a love for color and individuality. We welcome you to pay us a visit and enjoy paintings, photography, jewelry and sculpture.

Reviewed By Steve Q - Rock Hall, Maryland

Not one painting of ducks, sailboats, or dogs to be found! Eclectic, tasteful art that changes on a regular basis when one “show” ends and another begins. Owner is super friendly and helpful! Check it out, you will be glad you did!Steve Q! thank you for visiting our art gallery and thank you for your understanding of our mission to provide a different experience to the patrons of the arts in Chestertown. We are excited to be here!

200 High St, Suite 2, Chestertown, MD 21620-1586 +1 410-490-1140
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3 based on 1 reviews

Pam Foss Sculpture Gallery

The Pam Foss Sculpture Gallery combines a fine sculpture gallery with a working studio. Visitors to the gallery have the opportunity to see master sculptor, Pam Foss, creating new sculpture in her studio as well as view an eclectic selection of beautiful work in bronze, paper and Styrofoam currently on display. Pam is currently working on a major commission featuring three life-size St Bernard's in bronze that will be installed at Ohio State University's Veterinary Center at Columbus, Ohio in 2015. Visitors are welcomed to stop by and view the progress on the sculptures.

Reviewed By awjoseph66 - chevy chase

Lovely historic town to do walking tour and browse shops with a number of restaurant choices after Christmas.

6. Chestertown Electric

324 Cannon St, Chestertown, MD 21620-1328 +1 410-778-0313

Early electricity in the home - lamps, telephones, ceiling & desk phones, wall outlets/plugs/switches, heaters, motors, and other curios. Touch and use the items and learn how they work, Most items are for sale. Restoration services and lamp rewiring available. Specializing in antique fans.

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