5 Things to Do in May in Chestertown

In May, Chestertown, Maryland offers a range of activities and experiences to enjoy. Here are five things you can do:

  1. Attend the Chestertown Tea Party Festival: Join in the town’s iconic annual event that commemorates the historic Tea Party incident. Enjoy reenactments, parades, live music, food vendors, and immerse yourself in the town’s rich history.
  2. Explore the Farmers’ Market: Visit the local Farmers’ Market held every Saturday morning in Fountain Park. Discover fresh produce, locally made crafts, delicious baked goods, and engage with the friendly community.
  3. Take a River Cruise: Embark on a scenic river cruise along the Chester River. Enjoy breathtaking views, learn about the area’s ecology and history, and relax as you glide along the water.
  4. Visit the Galleries: Discover the vibrant art scene in Chestertown by exploring the town’s galleries. Admire the works of local and regional artists, ranging from paintings and sculptures to ceramics and photography.
  5. Visit Washington College: Take a stroll through the picturesque campus of Washington College, the tenth oldest college in the United States. Explore the historic buildings, beautiful gardens, and learn about the college’s rich history.

These activities in May will provide a diverse and memorable experience, showcasing the history, culture, and natural splendor of Chestertown, Maryland.

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Chestertown, Maryland was founded in 1706. It was established as a port town and played a significant role in the colonial era, serving as a bustling trade hub along the Chester River. Today, Chestertown retains much of its historic charm and is known for its well-preserved 18th-century architecture and vibrant cultural scene. Thanks for checking us out!




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Kent County Visitors Center
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122 N. Cross Street
Chestertown MD 21620


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Chestertown MD 21620

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