Maryland is the perfect vacation destination for those who love the outdoors. Chesapeake Bay activities are everywhere: hop in a kayak, go for a scenic drive, or play a round of golf. Featured below are some the of the many options for adventurers that our guests have access to in the surrounding area. Whatever you decide to do, Maryland’s incredible outdoor experiences can add something special to every trip. Book a getaway at our Chestertown B&B to experience the best of Maryland’s outdoor adventures!
On the Water
Blue Crab Chesapeake Charters – We highly recommend the sunset cruises.
Chester River Kayak Adventures – They have kayak, SUP, and sailboat rentals.
East Neck Boat Rentals – Go crabbing, fishing, or bird-watching and experience all the natural beauty the area has to offer.
The Chester River Packet Company, LLC – Embark on a scenic sunset cruise or day trip with a wide variety of options and packages to choose from.
National Scenic Byway – This scenic route works its way through historic towns, fishing and boating spots, and gorgeous natural scenery. An adventure you won’t want to miss!
Chesapeake Wine Trail – Great Oak Manor happens to be in the middle of the Chesapeake Wine Trail, putting us within minutes of several wineries.
Crow Vineyard & Winery – Tasting Room is open each day from Noon to 5 pm.
Clovelly Vineyards – Call ahead, 410-708-1775, to arrange tours and tastings.
Biking, Kayaking, & More
We provide cruiser bicycles (4 available) as well as a biking tour map to any interested guests.
Kayak, paddle board, and canoe right off of our beach available for guest use on first come first serve basis.
Rock Hall’s Eastern Neck Wildlife Refuge has several different trails to explore and is great for biking or kayaking.