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!

Sailboats on Chesapeake Bay

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.

Couple walking through a vineyard in Chestertown, MD

Driving Tours/Trails

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.

Kayak and chairs on the beach at our Cheaspeake Bay B&B

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.

Man golfing while enjoying a Chesapeake Bay, MD getaway

Golf

Great Oak Landing Marina – 9 hole course, free use to our guests.

Chester River Yacht & Country Club  – 18 Hole Course, talk to us for access and tee times.