City Guides: Things to do While Boating in Chestertown, Maryland
Chestertown, nestled along Maryland’s Chester River on the Eastern Shore, is a historic gem known for its colonial architecture, waterfront charm and vibrant arts scene. Founded in 1706, the town preserves its heritage beautifully, inviting visitors to explore brick-lined streets, stately homes and maritime history at every turn.
Add a few of these sites to your itinerary the next time you’re hanging out at a private boat slip near me, a charming resort or a local marina.
Chestertown Historic District
Chestertown Historic District is one of Chestertown’s most beloved attractions. You’ll find well-preserved 18th- and 19th-century buildings that create an immersive walk through time. Centered around the Chester River, the district features brick-lined streets, Federal and Georgian architecture and centuries-old homes that reflect the town’s prosperous 18th-century port era.
Enjoy landmarks like the Custom House, Emmanuel Church and the historic courthouse, along with boutique shops and inviting cafés. The district hosts vibrant events such as the Chestertown Tea Party Festival, which celebrates local Revolutionary War history. Nature lovers moored at private boat slips for rent appreciate the Chester River waterfront, which is perfect for kayaking, sailing and riverside strolls.
Garfield Center for the Arts
Garfield Center for the Arts, housed in the historic Prince Theatre, hosts performances, musicals, concerts, improv shows and community events that animate the town’s cultural life. Since its reopening in 2001 and subsequent renovation in 2011, it has become one of Maryland’s premier live theaters to visit from a private boat lift for rent.
Sultana Education Foundation
The Sultana Education Foundation offers interactive experiences aboard the Schooner Sultana, a meticulously crafted full-scale replica of a 1768 schooner that sails the Chester River and teaches visitors about ecology and colonial history. Students raise sails, navigate using 18th-century techniques and test water quality. Explore hands-on learning focused on Chesapeake Bay history, ecology and stewardship.
SEF also runs land-based education at its Holt Education Center and the Lawrence Wetlands Preserve. Through partnerships—including with the National Park Service—for programs like the Star-Spangled Banner National Historic Trail, SEF serves over 10,000 young learners annually.
Eastern Neck National Wildlife Refuge
On an island where the Chester River meets the Chesapeake Bay, it just makes sense to get outdoors and explore coastal habitats. The 2,285-acre Eastern Neck National Wildlife Refuge is home to bald eagles, waterfowl and serene walking trails.
Founded in 1962, it provides crucial habitat for migratory and wintering waterfowl, including tundra swans and more than 240 species of birds. With marshes, forests, grasslands and ponds, the refuge supports diverse wildlife such as deer, foxes and beavers. Hiking enthusiasts can hike seven trails, bird-watch, fish, picnic and explore a historic hunting-lodge visitor center.
Washington College
Washington College, one of the nation’s oldest institutions, enriches the community with art galleries, lectures and public events such as concerts, theatrical performances and dance productions in its Gibson Center for the Arts. The Kohl Gallery features rotating visual art exhibits and public lectures and readings by writers, artists and scholars.
Through its Center for Environment & Society, Washington College also offers environmental symposia, Earth Day programs, waterfront festivals and community-driven conservation projects.
Whether you're exploring its history, enjoying outdoor adventures or immersing yourself in the local arts, Chestertown offers a timeless blend of culture, nature and small-town charm to engage in from private boat docks for rent..
