- Our list of the best things to do in Chestertown, Maryland, features the top 87 nearby activities — including 35 great attractions with user approval ratings of 90% or more!
- Chestertown, MD has a variety of great sights and experiences nearby. Top categories include: Outdoor Places, Sights & Landmarks, Museums & Galleries, and Entertainment & Shows.
- The results below include the top 9 things to do within the city of Chestertown, MD , followed by 78 popular activities in nearby cities, including Stevensville, Havre de Grace, Pasadena, Middletown, Rock Hall, Dundalk, Essex, Queenstown, Smyrna, Perry Hall, Annapolis, Baltimore, Easton, Clayton, Bel Air and North East
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0.0 Miles
Enjoy a wide array of Craft distilled spirits in Chestertown’s historic district
0.7 Miles
100%
9 votes
101 Church Alley, Chestertown, MD 21620
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The Historical Society of Kent County features a collection of preserved documents, artifacts, and other information related to the county's history. The society offers a variety of programs and exhibits from their museum and research library.
0.7 Miles
82%
17 votes
315 High Street, Suite 106, Chestertown, MD 21620
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River Arts Chestertown showcases a wide range of works created by local artists, including ceramics, paintings, jewelry and photographs. In addition to their many exhibits, they regularly host classes, lectures and special events.
0.7 Miles
The Artists' Gallery is an art gallery displaying the paintings and other creations of six local artists. In addition to paintings, the gallery also displays high quality handmade crafts, including jewelry, ceramics, and many others.
3.6 Miles
ROLPHS WHARF MARINA is a local marina located on the scenic Chester River. The marina offers a number of services and amenities to its customers, including a ship store, a beach bar, a pool, and gas and diesel fuel available.
0.8 Miles
Theatrical and musical productions are performed at the Prince Theatre, which has recently been renamed as the Garfield Center for the Arts. Along with live productions, the venue hosts multiple workshops for youth and an educational outreach program.
0.8 Miles
Featuring exhibitions from national and international artists, The Carla Massoni Gallery is an art gallery offering a number of works available for purchase. A large variety of exhibitions are displayed throughout the year.
0.9 Miles
In close proximity to a boardwalk, Chestertown Marina has a dock for a variety of sea vessels, and is surrounded by local gift shops and restaurants. The marina has a store where visitors can buy equipment for their boats.
0.6 Miles
The small Chester 5 Theatres maintains only five screens, but first-run popular films are shown at the cinema. Movies are screened both as matinees and evening shows with a special discount applied to those screened before 6pm.
2.7 Miles
Both traditional ten pin bowling and duck pin bowling are offered at the Queen Anne's Bowling Centre. Along with the 24 lanes for bowling, there is a small on-site restaurant and a 14-hole miniature golf course.
10.5 Miles
The Mainstay plays jazz, classical, and classical blues music in a comfortable acoustic setting. The guests are seated very close to the performers. They have a hundred twenty mismatched chairs, old rugs, and a small stage.