- 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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44.5 Miles
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0 votes
Windward Keys Resort,, Rt 261, Chesapeake Beach, MD 20732
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Featuring a professional that formerly ranked 17th in the Mid-Atlantic Region, Chesapeake Beach Tennis Lessons provides students with the opportunity to learn from a National Tennis Academy certified instructor. The classes teaches students skills like serving, footwork, volleys, and more.
44.6 Miles
One half of the Delaware Stadium Corporation, the Daniel S. Frawley Stadium is a premium sports arena and event space in Wilmington, Delaware. It hosts baseball games, concerts, conventions, religious revivals, corporate events and other large-scale productions.
44.7 Miles
Located right on the water, Sailwinds Park is a green space that offers scenic views and a number of amenities. A kids' play area has various nautical-themed playground equipment, and a central building has restroom facilities.
44.7 Miles
Bringing arts to the East Maryland community, Dorcester Arts Center offers an array of activities related to visual, performing and literary arts. This includes art classes as well as exhibits and live, stage performances.
44.8 Miles
73%
151 votes
550 South Justison Street, Wilmington, DE 19801
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Birthday parties and special meetings can be held at the Delaware Children's Museum. There are all sorts of entertainment opportunities in here, all of them having an educational purpose – whether it is the coloring program or the stratosphere.
44.8 Miles
90%
49 votes
2 Rose Hill Place, Cambridge, MD 21613
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The Visitor Center at Sailwinds Park East in Rose Hill Place has picnic tables, a landscaped mini-ecosystem, some bench swings, and a playground in the park where kids can play.
44.8 Miles
Penn Cinema Riverfront is a 15-theater multiplex featuring the latest technologies, including IMAX and 3-D. See the latest Hollywood blockbusters in their comfortable stadium seating while enjoying fresh, affordable concessions.
44.8 Miles
Visitors who are interested in learning about Dorchester County's influence on the wooden sailing vessels of the Chesapeake Bay may enjoy what the Richardson Maritime Museum has to offer. The site's collection includes model ships, boat builders' tools, and watermen's' artifacts.
44.8 Miles
65%
31 votes
510 Justison Street, Wilmington, DE 19801
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An entertainment center, Stratosphere Trampoline Park provides trampoline-related activities including dodgeball, basketball and the Hubble Bubble. The park also offers a hurricane simulator, climbing walls, a mechanical bull, arcade game machines and a laser maze.
44.8 Miles
Featuring works from a number of local artists, Joie de Vivre Gallery is an art gallery popular among local art lovers. The gallery offers a variety of works, including paintings, jewelry, photographs, and much more.