- 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 51-60 of
656
22.5 Miles
100%
4 votes
126 Patriot Drive, Middletown, DE 19709
MoreLess Info
Jump on Over Inflatable Party & Play Center is a play center featuring numerous inflatables for children to play on. Jump on Over offers daily open jump sessions, is available for private party hosting, and hosts occasional special events.
22.6 Miles
The Upper Chesapeake Bay Charters is a full-time charter service that offers fishing trips, crabbing tours, kid's excursions, and a variety of cruises. The fishing charter company operates on the Chesapeake Bay.
22.6 Miles
-
0 votes
516 Eastern Blvd, Essex, MD 21221
MoreLess Info
Preserving the region's heritage, Heritage Society of Essex & Middle River Inc has a museum open to the public on Sundays. The museum features documents, photographs, and other artifacts that depict the community's history.
22.7 Miles
77%
111 votes
3417 Eastern Boulevard, Baltimore, MD 21220
MoreLess Info
In continuous operation for over 60 years, Bengie's Drive-In Theatre offers double and triple features in a classic drive-in movie setting. The theater features a variety of concessions, as well as some video games.
22.7 Miles
Old Town Parasail, located in Havre de Grace Maryland, features parasailing, boat rides and kayak and pedal boat rentals to area visitors. Parasailers enjoy panoramic views of the Chesapeake Bay and the surrounding area.
22.7 Miles
100%
31 votes
100 Bourbon Street, Havre de Grace, MD 21078
MoreLess Info
Baysail School & Yacht Charter - Day Tours offers bareboat, captained, or instructional charters on fully equipped new or recent yacht models. The facility also offers smaller sailboats for half or full day rentals.
22.8 Miles
100%
7 votes
121 North Union Ave, Suite C, Havre de Grace, MD 21078
MoreLess Info
Built in 1955, the Skipjack Martha Lewis is a historical ship located on the Chesapeake Bay. The boat was the last to commercially fish in the Chesapeake Bay oyster fleet in the United States of America.
22.8 Miles
The Levels Road Dog Park is composed of two different areas that are connected by a trail. Visitors and their dogs are able to walk along two miles of trails in total from the early morning to sunset.
22.9 Miles
The Watersedge Recreation Council handles all the local amateur sports programs for the Watersedge community and its veterans. Baseball and Basketball are featured along with dance lessons and community events year-round.
23.0 Miles
35%
26 votes
9010 Ft. Smallwood Road, Pasadena, MD 21122
MoreLess Info
Compass Pointe Golf Courses is a 36 hole championship golf course designed by Lindsay Ervin. The course features a varied terrain with woodlands and trimmed greens.