- 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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27.9 Miles
SegZone is a local tour operator which specializes in guided eco-friendly Segway tours of Annapolis and its numerous historic sites featuring colonial architecture as well as many other local attractions.
27.9 Miles
Watermark, formerly known as Chesapeake Marine Tours, is a local tour company which organizes a variety of cruises and private charters to introduce visitors to the history and culture of Annapolis with the help of guides dressed in colonial period costumes.
27.9 Miles
Featuring a permanent exhibit, Annapolis Maritime Museum is filled with artifacts detailing the ecological and maritime history of the region. The museum hosts special events like a summer concert series, art exhibits, and lectures.
27.9 Miles
Annapolis Tours & Crawls offers a variety of walking tours, pub crawls, and combinations of the two in the downtown Annapolis area. Offerings include a craft beer pub tour and a ghost tour.
27.9 Miles
Arts and architecture of the 18th century is on display at Hammond-Harwood House. Take a tour to see exhibits like a gentlemen's study. Colonial guides are on hand to provide a more detailed account of the displays.
27.9 Miles
Undergraduate and graduate programs are offered at St. John's College, located in Annapolis. The on-campus library provides a quiet place for students to read and study. Programs and events are held year round.
27.9 Miles
Visitors to the William Paca Garden can enjoy serenity and beauty with a 45-minute tour, offered daily (fee applies). The two-acre garden is located at the Paca House, a restored 18th-century mansion reflecting the English country villas of the time.
27.9 Miles
With direct access to Spa Creek, Annapolis Canoe & Kayak offers visitors watercraft rentals to take out on the water. Visitors can rent kayaks and canoes for the day, as well as stand up paddle boards and power boats.
28.0 Miles
Built in 1772, Maryland State House is the oldest operating state capitol in the country and features the largest wooden dome built in America without the use of nails. Guided tours of the capitol and the surrounding gardens are available.