Chestertown Historic District
Step back in time at the Historic District, where centuries-old homes tell the story of the town’s rich heritage. The district hosts the Chestertown Tea Party Festival, a signature highlight that brings history to life each spring with reenactments, period costumes, live music, and colonial-era demonstrations honoring the town’s role in American history.
See MoreChestertown RiverArts
As Maryland’s designated Arts and Entertainment District, downtown Chestertown is a hub for creativity, offering galleries, theaters, live music venues, and artisan shops that showcase local talent. The district hosts regular events that draw both locals and visitors, from gallery openings and theater productions to outdoor concerts and seasonal festivals. Street performances and craft markets create an energetic and engaging experience, while the nearby riverfront offers scenic spots for relaxation and people-watching.
See MoreChester River
In the Fall, the Downrigging Festival takes center stage along the Chester River, celebrating the town’s maritime heritage with tall ships and a bluegrass festival. The festival draws sailors, visitors, and locals together for a weekend of fun, music, and riverfront festivities. The River also provides endless opportunities for boating, kayaking, paddleboarding, and fishing, with both quiet coves and open waters to explore.
See MoreGarfield Center for the Arts at the Prince Theatre
The town’s dedication to arts and culture is evident at the Garfield Center for the Arts, a hub for creativity offering theater productions and community events. Along with galleries and performance venues, the center supports local artists and performers while fostering a vibrant cultural scene.
See MoreSumner Hall
Sumner Hall, a historic African American cultural center, stands as a testament to the town’s commitment to preserving and sharing the stories of its Black community. The center hosts educational programs, exhibits, and events that highlight local history and promote understanding, connecting past generations to the present.
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