- 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
30.9 Miles
90%
10 votes
213 N Talbot St, St. Michaels, MD 21663
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Using an uncommon and historic variety of boat called a skipjack, Chesapeake Skipjack Sailing Tours offers a variety of boat tours of the Chesapeake Bay area. The company can cater picnics, or visitors can bring their own food and drink.
30.9 Miles
95%
274 votes
272
Patriot Cruises
At the foot of Cherry Street, St. Michaels, MD 21663
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Patriot Cruises offers cruises on their two-level 149 passenger boat on the Miles River, part of the largest estuary in the Western Hemisphere. While onboard, listen to a historic narrative of the area, enjoy drinks from the full bar, and buy food.
30.9 Miles
From stuffed animals to puzzle games, Calico Toys & Games offers two stories of classic and modern toys for children. The first floor has an art gallery featuring the work of local artists.
30.9 Miles
A central hub of the local cultural scene, the Academy Art Museum provides a variety of opportunities for education and growth in the arts. Visitors can explore permanent and temporary exhibits or sign up for a hands-on class.
30.9 Miles
Homeport Farm Park provides visitors with opportunities for kayaking and canoeing in South River. The park has a variety of walking trails, and features a historic tobacco barn on the property.
31.0 Miles
Get ready to scream at Frightland in Middletown, Delaware. This ultimate haunted attraction is open to patrons aged 12 and up. Ticket prices do not include parking, which is on a donation basis that benefits leukemia research in Delaware.
31.0 Miles
Frivolous Fibers is a store, gallery, class room, and social event space for those who love knitting, crocheting, and stitching. Store events include weekly crochet and knit sessions as well as occasional sheep sheering events.
31.1 Miles
Sail Selina II is a local tour operator which offers sailing cruises on the Chesapeake Bay aboard their vintage catboat named Selina II.
31.1 Miles
The Spa at Harbour Inn offers Swedish massage, deep tissue massage, hot stone therapy, Wild lime scalp and body massage, Reiki, reflexology, body wraps, and waxing. The spa also offers a full array of nail treatments.