- 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
Showing 411-420 of
656
37.3 Miles
Crofton Bowl offers 48 lanes of bowling, as well as a snack bar and a lounge with Keno machines. They offer bumper bowling for kids, league play, and automated scoreboards.
37.3 Miles
From league to recreational bowling, Crofton Bowling Centre is a bowling alley with a pro shop and shoe rentals. Every Friday and Saturday night, the alley hosts an event where visitors can bowl to a live DJ and flashing lights.
37.4 Miles
The 4 mile-long trails, the playgrounds, the picnic areas, the different sports courses, all of these and others make White Clay Creek State Park worth the while. Fishing enthusiasts can also find 2 ponds inside the park.
37.5 Miles
100%
3 votes
21604 Chicken Point Road, Tilghman, MD 21671
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Dockside Express Cruises & Tours - Day Tours offers a variety of tour packages on its 49-seat Express Royale boat. Options include floating crab feasts, private charters, team-building exercises, and overnight excursions for groups of at least 25.
37.5 Miles
100%
25 votes
21604 Chicken Point, Tilghman, MD 21671
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Phillips Wharf Environmental Center is an educational attraction designed to teach visitors about the various animals of the Chesapeake Bay area. It offers hands-on experiences with animals, and features an ecological focus.
37.5 Miles
The Tilghman Watermans Museum is dedicated to celebrating and commemorating the Tilghman Island watermen and their history and traditions. It collects models of boats as well as examples of traditional tools used by the watermen.
37.7 Miles
Christiana Skating Center is not only a place suited for roller-skating and learning new tricks. Besides the themed parties held on holidays such as Halloween, this establishment is also suited for all kinds of celebrations, such as birthday parties.
37.7 Miles
Renaissance Fine Arts houses the largest collection of art in the Mid-Atlantic region. They offer traditional and contemporary art with a diverse collection that ranges from original works on canvas and paper to sculpture with their Master Works gallery.
37.8 Miles
89%
18 votes
5907 Tilghman Island Road, Tilghman, MD 21671
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Chesapeake Lights is a local tour operator which offers a variety of guided tours of the Chesapeake Bay and the surrounding lighthouses.
37.9 Miles
Enjoy a live show at Oregon Ridge Dinner Theatre, performing home of the Baltimore Actors' Theatre. Each show features 35 to 50 performers in complete costume with live musical accompaniment.