Tucked along the scenic Chester River in Kent County, Chestertown, Maryland is a historic gem that offers a beautiful blend of small-town charm, waterfront beauty, and vibrant local culture. Whether you’re planning a day trip, a weekend getaway, or considering a move to the Eastern Shore, there’s no shortage of things to do in Chestertown, MD.
From riverside strolls and live music to colonial festivals and cozy cafés, this charming town invites visitors to slow down and soak in the local flavor.
Explore the Historic Downtown & Waterfront
Start your visit in Chestertown’s historic district, one of the oldest in Maryland and listed on the National Register of Historic Places. Brick sidewalks, 18th-century architecture, and sweeping water views make every corner photo-worthy.
Take a stroll along High Street and Water Street where you’ll find local boutiques, bookshops, antique stores, and riverside cafés. Don’t miss a walk down to the public landing at the foot of High Street—especially at sunset.
Arts, Culture & Local Events
Chestertown is a designated Maryland Arts & Entertainment District, and it shows. Explore rotating exhibits at RiverArts Gallery, discover fine art at MassoniArt, or take a pottery or printmaking class. The Garfield Center for the Arts hosts performances year-round—from indie films to community theater and concerts.
On First Fridays, downtown shops and galleries stay open late with special exhibits, street music, and festive vibes—perfect for a date night or family outing.
Festivals & Seasonal Highlights
One of Chestertown’s signature events is the Chestertown Tea Party Festival, held every Memorial Day weekend. This lively celebration includes a colonial reenactment, parade, local vendors, and even a raft race.
Other seasonal favorites include:
- Music in the Park – Free summer concerts at Wilmer Park
- Fourth of July Fireworks – Over the Chester River
- Dickens of a Christmas – The first week in December
Dive Into Local History
History lovers will appreciate the Historical Society of Kent County and the self-guided walking tour apps that bring the town’s past to life. Learn about Chestertown’s revolutionary roots at the Tea Party Museum, and visit the Custom House at Washington College, home to the C.V. Starr Center for the Study of the American Experience.
Outdoor Activities & Water Adventures
Love the outdoors? Rent a kayak or paddleboard and launch right into the Chester River. Wilmer Park offers a riverside walking path, playground, and open green space perfect for picnics and sunset views.
For nature just outside of town, check out the Eastern Neck National Wildlife Refuge for birdwatching and hiking trails!
Shopping, Dining & the Farmers Market
Chestertown’s shopping scene mixes local charm and artisan flair. Find handmade goods, art, vintage finds, and gifts at shops along High Street. On Saturday mornings, the Chestertown Farmers & Artisans Market is the place to be—filled with fresh produce, baked goods, flowers, and crafts.
Washington College Experience
Founded in 1782, Washington College adds youthful energy and academic depth to Chestertown. Visitors can explore the historic Hynson-Ringgold House, attend public lectures, or check out a concert or art show hosted by the college.
Family-Friendly & Pet-Friendly Fun
Looking for family-friendly things to do in Chestertown? Head to Wilmer Park’s playground or plan a seasonal outing to Lockbriar Farms for fruit picking, ice cream, and hayrides. Many downtown shops are pet-friendly, and several events throughout the year welcome the whole family—furry friends included.
Practical Info & Local Tips
Chestertown is very walkable with plenty of free parking downtown. The best times to visit are spring through fall, when events and festivals are in full swing. Don’t forget your camera—those riverside sunsets are unforgettable.
Thinking About Calling Chestertown Home?
If Chestertown’s charm has you thinking about putting down roots here, you’re not alone. From historic homes and waterfront cottages to cozy bungalows, there’s something for every lifestyle.
👉 Browse homes for sale in Chestertown, MD
👉 Explore nearby communities like Rock Hall & Kennedyville
👉 Contact Lynn and Julia for more local guidance!
We’re local agents who live and work here—and we’re ready to help you find your perfect place on the Eastern Shore!
