- 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 141-150 of
656
27.5 Miles
Sipping Pretty conducts in-home, corporate, non- profit and specialty event wine tasting seminars. They also coach one-on-one seminars for educational purposes, specialize in custom baskets, chef services and wine accessories.
27.5 Miles
100%
2 votes
551 Baltimore Annapolis Blvd, Severna Park, MD 21146
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Not only can Rockwell Fitness Center visitors utilize the location's wide range of workout equipment, but they can also purchase healthy foods for consumption on-site. The location also offers yoga and weight loss programs.
27.5 Miles
100%
3 votes
623 Baltimore-Annapolis Blvd, Severna Park, MD 21146
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Visitors can enjoy an aquatic center, fitness equipment, 3 dance studios, and a gymnasium at the Severna Park Community Center. The community center offers dancing and swimming classes and offers 36,000 square feet of meeting and recreation space.
27.5 Miles
Providing a variety of aquatic activities to the community, SPCC Aquatics has a lap pool where visitors can take swimming lessons. The center has public swim hours where visitors can use the pool for laps or freestyle swimming.
27.6 Miles
Specializing in children's fitness and entertainment, Rolly Pollies Llc offers an open gym, bounce house, and foam pit to its visitors. The gymnasium is supplied with equipment like bars, pads, and ramps.
27.6 Miles
Freetown Park is a public park location offering a large number of amenities for its visitors to enjoy. These amenities include a baseball field, a basketball court, a playground structure, and a walking trail.
27.8 Miles
One of the oldest service academies in the country, the U.S. Naval Academy provides undergraduate training to students who serve as officers in Navy and Marine Corps post-graduation. Visitors are invited for guided tours of the campus which includes museums, visitor center and more.
27.8 Miles
Private sailing excursions are offered by Classic Sail Charters for groups of up to six people. The service provides half day, full day, or sunset cruises within the waters of the Chesapeake Bay.
27.9 Miles
98%
202 votes
311 Third St., Annapolis, MD 21403
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Pirate Adventures on the Chesapeake offers kids a chance to spend a day as a pirate aboard a replica of pirate ships where they are engaged in a variety of hand-on activities including face-painting, treasure hunt and more.
27.9 Miles
Schooner Woodwind is a local tour operator which organizes a variety of sailing trips and private cruises on the Chesapeake Bay aboard their two 74-foot long schooners called Woodwind and Woodwind II.