- 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
0.0 Miles
This bistro draws from culinary influences as diverse as Italy and St. Louis, and showcases fresh Chesapeake Bay seafood in many dishes
10.5 Miles
Featuring a 42 foot glass diesel powered charter boat with six-person capacity, Misty Charters leads fishing trips in Chesapeake Bay. The company can accommodate casual trips as well as customized tournament fishing trips.
10.6 Miles
67%
18 votes
P.O. Box 189, 5758 Main Street, Rock Hall, MD 21661
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Guests will experience an amazing tour of the tidal waters of the Chesapeake Bay with Chester River Kayak Adventures. Their tour guides will assist you from beginning to end. Eagles, ospreys, ducks and other wildlife can be seen during the trip.
10.6 Miles
100%
251 votes
21211 Rock Hall Ave., Rock Hall, MD 21661
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Blue Crab Chesapeake Charters is a local tour operator which organizes sightseeing and sunset sailing cruises on the Chesapeake Bay.
10.6 Miles
Grays Inn Creek Marina offers boat storage, maintenance, and docking services, as well as slip rentals with electric service. The Marina offers a prime fishing location and conditions, as well as access to scenic secluded inlets.
11.1 Miles
Cruises around the Chesapeake Bay are provided by Blown Away Sailing, which also offers destination cruises to Baltimore and Annapolis. Guests can even participate in sailing courses with the company's instructors who are certified by the American Sailing Association.
11.1 Miles
Located on the scenic Chesapeake Bay, the Haven Harbour Marina is a marina offering a number of facilities and amenities for its guests to enjoy. Yacht services, pool access, and dockside parking are among the many amenities available.
11.3 Miles
Wayne Gatling Guide Service has been in business for more than thirty-five years. They are available for fishing trips, and are very much experienced with waterfowl hunting. Captain Wayne knows his waters and he also knows all the best restaurants to get your fish cooked.
16.7 Miles
Queenstown Harbor Golf Links comprise of two links golf courses which feature two distinct layouts namely the River and the Lakes, both of which offer beautiful views of the Bay.
17.1 Miles
78%
76 votes
441 Outlet Center Drive, Queenstown, MD 21658
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Queenstown Premium Outlets is a factory outlet store which offers a varied selection of brands including Gucci, Nike, Polo Ralph Lauren and more, in addition to a number of eateries.
18.1 Miles
Spread over 375 acres of land, the Rocky Point Beach is situated at the mouth of both the Middle and Back Rivers along Chesapeake Bay. Along with the 300 foot beach, the surrounding park has numerous picnic areas, two playgrounds, a fishing pier, and a sailing center.