Our Favorite Activities at Great Oak Manor

Great Oak Manor is the perfect place to spend your summer days. Wander down to our private beach and stick your toes in the water. If you’re feeling adventurous, take out one of our kayaks or stand-up paddle boards to explore the shallows of the bay.

Not a water person? You can still enjoy the gorgeous waterfront views from our back lawn. Plop down into a hammock with your favorite book or one from our library to unwind and relax.

There is also a ton to do in Chestertown and surrounding Kent County. From museums to wineries, you can easily spend the day traipsing around!


Photo by Rodrigo Rodriguez on Unsplash

Massey Air Museum, Inc.

A living airport-museum with collections of vintage aircrafts, artifacts, reading materials, and touch-and-feel exhibits. Visitors can tour the museum and hangars, and the restoration shop operates most days. You can also schedule open-cockpit biplane and glider experiences.

Waterman’s Museum

A fishing shanty and artifacts from the early days of oystering, crabbing, and fishing are on display at the Waterman’s Museum. Visitors can also view photos of past and present watermen.

Kent Museum
A collection representing the rural heritage of agriculture and domestic life in Kent County.

Kent County is a picturesque destination with lots of exciting things to do. Below are some self-guided and guided tours that you may find of interest!

Eastern Neck National Wildlife Refuge
Eastern Neck National Wildlife Refuge is a 2,285 acre island providing habitat for thousands of wintering waterfowl. The refuge offers wonderful wildlife viewing and expansive views of the Chester River and Chesapeake Bay along 7 different trails.

Chestertown’s Historic Waterfront
Learn all about Chestertown and its past including Revolutionary War soldiers and heroes from the Underground Railroad.

African American History
There are nearly 30 stops on this self-guided tour through Chestertown and its African American history.

Bike Tour
With miles of flat, lightly traveled roads, the county offers an ideal environment for the bicycle enthusiast.

Driving Tour
This driving tour marks out nearly 110 miles and marks points of interest and historic sites outside the major towns.

Wineries & Distilleries

Cassinelli Distillery
The Cassinelli distillery and wine bar is located at 323 High Street in Chestertown and is open Thursday through Monday.  Visitors can watch as distilled products, including vodka, gin and brandy, are made and taste them from directly from the stills.

Clovelly Vineyards
Clovelly is a third-generation Maryland Eastern Shore farm with vineyards overlooking a beautiful bend in the Chester River.

Crow Vineyard and Winery
Crow Vineyard and Winery is another third-generation farm and winery in Kent County. The tasting room offers a variety of hand-crafted wines and you can add a pairing tray made from  local grass fed Angus Beef and other farm grown items.