Uncover the Best of Chestertown

A Haven for Art & Culture

Discover the vibrant culture and endless possibilities that wait you in Chestertown. Whether you’re seeking outdoor adventures, artistic inspiration, or simply a leisurely stroll through our charming streets, Chestertown offers something for everyone.

Whether you’re a visitor or a longtime resident, there’s always something new to discover in our vibrant town!

Things to Do

Two kids blurred walking in front of art on the wall at Massoni Art Gallery

Arts & Entertainment

Martha Washington Square at washington college

Washington College

Two kids blurred walking in front of art on the wall at Massoni Art Gallery

Kid Friendly Activities

Downtown Cross Street in Chestertown during the day

Self Guided Walking Tour

Chestertown Farmers Market booth with customers

Farmers & Artisans Market

Shopping downtown in Chestertown


Customers dining outside in front of the Kitchen in Chestertown, Maryland under an umbrella table


Outdoor Sculpture Tour

Discover the beauty of Chestertown’s public art! From the historic waterfront to the newest parks, public art will soon adorn every corner of our town. Keep an eye out for these stunning artworks as you explore, or immerse yourself in the experience with a guided walking tour to learn more!

Our Visitors Center

Unlock the Charm of Chestertown

Discover the insider knowledge on where to find the best cream of crab soup in town, indulge in the tastiest ice cream, and plan your visit to the art galleries. Let us guide you to create a spectacular experience in Chestertown that combines culinary delights, sweet treats, and a journey through the town’s vibrant art scene.

Immerse yourself in the local flavors with a bowl of the town’s renowned cream of crab soup, savor the sweetness of handcrafted ice cream, and explore the rich culture of Chestertown through its diverse art galleries. Let us be your tour guide!