- 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 281-290 of
656
31.1 Miles
The Hampton National Historic Site offers a glimpse into Colonial and early American lifestyles. Guided tours are available throughout the inside of the mansion as well as the outside which features the servants quarter and scenic gardens.
31.1 Miles
A 15-screen movie theater, Cinemark Towson & XD offers first-run feature films using digital projection and RealD 3D. The theater provides arcade game machines, a private event room, stadium seating and a cafe with food and drinks.
31.1 Miles
The St. Michaels Marina is a public marina that features a pool, a marine store, bicycle rentals, and a pump-out service. The marina also has a public boat launching ramp as well as showers and restrooms.
31.2 Miles
St. Michael's Museum is dedicated to preserving and celebrating local history. Housed in relocated buildings over a century old, it features collections of historical artifacts and curiosities. It offers guided walking tours of historical areas, as well.
31.2 Miles
64%
11 votes
722 Dulaney Valley Rd, Ste 187, Towson, MD 21204
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A flat track roller derby league made up of four intraleague teams and two interleague teams, Charm City Roller Girls is also skater owned and operated. Bouts are held at DuBurns Arena approximately once a month.
31.3 Miles
Saint Michaels Winery offers a variety of delicious red and white wines at reasonable rates. This small winery's tasting room is a nice open space with lots of natural light.
31.3 Miles
100%
12 votes
405 S. Washington Street, Easton, MD
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Originally built in the 1600s, The Third Haven Friends Meeting House is a Quaker church that consists of burial grounds, brick Greek Revival rooms, caretaker's cottages, and other structures. Worship meetings are still held in the church weekly.
31.3 Miles
94%
82 votes
605 S. Talbot St. #6, (In the Old Mill), St. Michaels, MD 21663
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The Lyon Distilling Company is a micro distillery that creates ultra small batches of Rum and Whiskey. The distillery makes white rums, dark rums, bourbon aged rums, corn whiskey, and rye whiskey.
31.4 Miles
Dover, Delaware is home to the Fordham Brewing Co. This micro-brewery is best known for its variety of ales. Visitors are always welcome, and tastings are available. The brewery also sells its wares at its gift shop.
31.4 Miles
At the Terrapin Station Winery, customers can purchase wines of its Diamondback Reserve, Terrapin Classics, and Pyrate Wines brands. The location's vineyard plantings include Cayuga, St. Vincent, and Marquette plants.