Adventures by Land and Water in Maryland

Our magnificent country estate on Maryland’s Eastern Shore offers stunning views of the Chesapeake Bay and is located minutes away from Chestertown. Be as active as you’d like, or simply relax – the options are plentiful. If you’d like a little adventure, read on to learn about some of our favorite outdoor activities – on land and water.


Couple Kayaking and Enjoying the Sunshine
Borrow one of our single or double complimentary kayaks and set off on your own to enjoy the beauty of the bay. The protected, shallow waters of the Chesapeake Bay and its many tributaries are excellent for kayaking. Take in the flora and fauna, as well as the abundant sea life including blue crab, common loon, tundra swan, brown pelican, double-crested cormorants, the world’s largest population of osprey, plenty of fish, and adorable river otters.

Paddle Boarding
Grab one of our complimentary on-site paddleboards and launch right from our own private beach. Or book an exciting tour through Barefoot Adventures, a local company that is committed to sharing their love of environmental stewardship and passion for the outdoors with others. They offer Stand Up Paddleboarding, Fishing (as well as Stand Up Paddleboard Fishing!), Scuba Instruction and Eco-Travel Adventures.



Attractive Couple Sailing and Drinking ChampagneChester River Packet Company offers scenic Chester River cruises on the River Packet, a 65-foot classic yacht. This 1920s-style tour boat is based in historic Chestertown, and offers a unique venue for both private events and public cruises. The crew will take care of every detail while you and your guests enjoy the surroundings and savor the culinary expertise of Occasions Catering.

Blue Crab Chesapeake Charters provides an award-winning sailing experience that you won’t want to miss! Take the helm or just sit back and relax on the “Island Girl”, a 43-foot Morgan sailboat with plenty of deck space, a comfortable interior and space for up to 6 people. Sail from Rock Hall Harbor into the open Chesapeake Bay or scenic Swan Creek. They offer Rock Hall’s Original Sunset Cruise, which will surely be a highlight for any visit to Maryland’s Eastern Shore. Excursions are offered 7 days a week from April through mid-November.

Relax and let us plan all the details when you book our Blue Crab Chesapeake Charters Sunset Sail Package. Your vouchers will be ready for you upon check-in for your pre-reserved sail on the Chesapeake. Enjoy a 1 ½ hour daytime or sunset sail from the Rock Hall Harbor and out onto the Bay. We’ll also have a gourmet wine and cheese picnic basket to take with you on your sunset sail. Available for a limited time only.



Check out one of our complimentary cruiser bikes, grab a trail map and hit the road (or trail). Take a leisurely bicycle ride on safe country roads, or a more secluded route on one of the many trails and enjoy the natural beauty of the surrounding area.

Couple Hiking in Fall


Eastern Neck Wildlife Refuge provides the perfect area for hiking, and is also open for hunting, fishing, bird watching, and other wildlife-related activities. There are activities available for the whole family year-round here, including environmental education and wildlife viewing and photography. The BayScapes program teaches homeowners and landowners about conservation landscaping, conserving water, using native plants, creating wildlife habitats, using Integrated Pest Management and planning for the long term. Biking is permitted on roads in the refuge as well, but not on trails.


Maryland’s Kent County is well known for its prime hunting experience and abundance of available hunting locations. Over 130,000 acres of agricultural land and over 200 miles of shoreline provide many choices such as waterfowl, white-tailed deer, turkey and more. There are many local guide services that often provide and maintain all the tools required for the ideal hunting experience, including pits, stands, stand-ups, blinds, calls and quality decoys. We will be happy to recommend guides in the area.


Great Oak Manor - Hodges Room with Fireplace

Great Oak Manor – Where Else?

Relax in a hammock after your adventures, sit and gaze at the bay in an Adirondack chair or stroll the expansive lawn and watch a spectacular sunset. Turn in to one of our 12 comfortable and stylish rooms. Choose one with a cozy fireplace, a spacious bath or inviting French doors leading to the garden. Wake up to a full breakfast in the dining room or on the terrace. Savor seasonal fresh fruit, homemade baked goods, cereal, and a hot entrée such as French toast, quiche, or egg strata.

Make that fall getaway happen and book your stay today!