- 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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656
41.8 Miles
93%
87 votes
12333 Quarterback Ct, Bowie, MD 20720
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Vino 301 Wine Concierge - Private Tours offers patrons tours of Maryland's wineries. Vino 301 provides Tour Ambassadors who share information with guests about Maryland's wine history. They offer several tour packages including Bachorelette, Birthday and Custom Wine Tasting Tours.
41.9 Miles
Centennial Park is a 325 acre park populated by fields, woodlands, wetlands, and a large lake. Visitors to the park can find picnic, playground, and sports areas, as well as a variety of wildlife.
42.1 Miles
Located on Fort Meade Road, Laurel, the Dutch Country Farmers Market has different kinds of food to choose from. Visitors have been raving about the homemade breads, pies, cakes, fruits, vegetables, meat, and more.
42.1 Miles
The man-made Lake Kittamaqundi offers 27 acres of water with a rough depth of around seven feet. Boating is the most popular activity on the lake as there is a large boathouse with a wooden pier located along the western shore.
42.1 Miles
Maryland City Park offers a wide range of amenities including baseball fields, paved trails, a playground and picnic areas. They also feature a dog park as well as fishing on the Patuxent River.
42.3 Miles
Wilmington & Western Railroad is the first railroad to be included in the National register of Historic Places. Opened as a tourist attraction in 1966, this 1870 railroad uses steam engines to transport children of all ages back in time, for all occasions, whether for romantic evenings or special celebrations.
42.3 Miles
A place to eat, drink, laugh, and have a good time is Toby's Dinner Theatre. Shows include Mary Poppins, The Wizard of Oz, and many more family classics to enjoy.
42.3 Miles
Focused on women's arts, Venus Theatre Play Shack is a women's theater group that puts on feminist themed productions. The group combs through hundreds of plays to select four plays to perform every year.
42.4 Miles
A movie theater featuring an IMAX auditorium, AMC Columbia 14 displays first-run feature films using digital projection and RealD 3D. The theater offers stadium seating, theater rentals, self-service ticketing and a concession area with food and drinks.
42.4 Miles
With 32 lanes of bowling available, the Brunswick Columbia Lanes seeks to provide fun and entertainment to those who visit. Amenities at Brunswick Columbia Lanes include a snack bar, pro shop, and billiards.