One of the best ways to enjoy the late summer is to get out on the water, where you can feel the breeze and admire the beautiful scenery of Maryland’s Eastern Shore. And you don’t need your own boat! Whether you’re paddling under your own power or letting the wind do the work, you’ll find several ways to drink in the summertime on the water in Dorchester County. Plus Dorchester has some new ways to enjoy, especially if you love the idea of being out for sunrise or sunset.

Sail on a skipjack.

Join a sail on the Skipjack Nathan of Dorchester, a traditional oystering vessel (pictured at top). Skipjacks are icons of the Chesapeake Bay whose sails were once seen all over — and now are few and far between. The sail includes stories about the local maritime history and a demonstration of oyster dredging. NEW: For the first time, the skipjack will offer a sunset cruise, complete with lite fare and non-alcoholic beverages (and BYOB) on Sept. 2.

SUP with Over Board Paddle and Fitness

Learn to SUP.

Stand-up paddleboarding is taking off all over the world, and you can learn to do it right here in Dorchester with Overboard Paddle & Fitness. Try a beginner class, arrange a custom outing for your group, or join a SUP yoga or SUP glow outing. You can also rent a SUP through Blackwater Adventures.

Hoopers Island Lighthouse

Go on a lighthouse tour — by boat.

Sawyer Charters has a few Chesapeake Bay Lighthouse Cruises coming up in September, when you can see six lighthouses around the Bay — including Hoopers Island Lighthouse here in Dorchester — and hear about their stories. Sawyer also offers sightseeing tours, sunset tours, fishing charters, and more.

Riverboat from Suicide Bridge Restaurant

Go on a riverboat.

Take a cruise on a paddlewheeler boat for a crab feast, lunch, dinner, or sightseeing cruise with Suicide Bridge Restaurant’s riverboats.

Blackwater Adventures

Paddle through beauty.

Rent a kayak or SUP through Blackwater Adventures at their location at Blackwater National Wildlife Refuge. Or visit their second o=location at the Hyatt Regency Chesapeake Bay Resort, for kayaks, SUPs, jetskis, small powerboats, and more. Plus, if you go to the refuge location, you can enjoy a meal right on site from Big Feller’s Hammock, a food truck operated b y the award-winning Bistro Poplar.

Stoney Cove Charters, Cambridge, MD. Photo by Dave Harp

Head out with a lifelong waterman.

Join Stoney Cove Charters for an outing on the water. You can even have a crab feast with the crabs you just caught!

0 Dark 30 Charters

Join a fishing charter.

We’ve got some great fishing in these parts. See our list of fishing/crabbing charters.

Print Friendly, PDF & Email