Raise the sails, rev the motor, or pick up a paddle to discover boating bliss on Maryland's Chesapeake Country Scenic Byway. Celebrate boating in all its forms on the welcoming waters of this area's canals and rivers—and, of course, the Chesapeake Bay.

The C&D Canal Museum (MD) [2]
From Chesapeake City on the byway’s northern end, you can access the busy transportation waterway, the Chesapeake and Delaware (C&D) Canal. Although you can’t sail, paddle, or tow a water-skier, you can cruise amidst barges and other commercial boats as long as your boat is motorized. Don’t have a boat of your own? Then join a canal tour and learn about canal culture from the knowledgeable captain. You can also stop at the Canal Museum in Chesapeake City to learn about the canal’s early days, from its manual labor-intensive construction to steam-powered ships and pump houses.
In Chesapeake City each June, come by boat to the Canal Day Festival. Take advantage of the free shuttle-boat service that brings you right to the harbor and the onshore festivities. Check out crafts, enjoy food, and listen to music during this celebration of the historic waterway that still hosts plenty of commercial and recreational boating today.
Fourteen miles south of Chesapeake City is Georgetown, one of three sites on the Sassafras River where you can launch a canoe or kayak. Paddle through marshlands, beaches, farmlands, and bald eagle nesting sites, where larger boats can't go. If you make your way west toward Betterton Beach where the Sassafras River meets the Chesapeake Bay, you can moor your canoe or kayak at the pier, not far from the public restrooms and bathhouse. Here you can picnic under the pavilion, or just watch swimmers enjoy the sandy beach and cool waters.

Sultana: "Schoolship of the Chesapeake" (MD) [4]
From the many port cities along the Chester River, including Chestertown, which is 15 miles south of Georgetown, voyage out on the Chesapeake Bay aboard the meticulously reconstructed historic schooner, Sultana. Help with the rigging during a two to eight hour public sail, or explore the crew’s quarters below deck during an open house when the boat is docked at a port city along the byway.
At Sultana’s homeport of Chestertown, celebrate the end of the sailing season with Downrigging Weekend. Watch, board, and even sail on one of the dozens of sailing ships arriving at the Chestertown harbor in late October and early November each year for this event.
For a less conspicuous, but equally enjoyable boating experience on the Chester River, launch a canoe or kayak at several launch sites and public docks from Chestertown’s riverfront High Street Park to Boggles Wharf on Eastern Neck Island. Canoe past private preserved 18th century homes lining the banks near the city and work your way through peaceful farmlands to the Eastern Neck Wildlife Refuge.
How Much Farther to the Water? (MD) [6]
Continue along the byway just past Queenstown and discover more boating waterways within the Chesapeake Bay Environmental Center. From here you can rent a kayak or canoe and glide through Marshy Creek, the Narrows, and Prospect Bay. Appreciate beautifully restored shorelines, natural marshlands, and abundant waterfowl, as you float on the tranquil waters of the self-guided trails in this area.
If that’s too quiet for you, head east of the Environmental Center to Kent Island in early August for the annual Thunder on the Narrows powerboat-racing event. Take your family to cheer on your favorite boat in each racing class, and grab something to eat from the on-site options when you’re hungry.
Get out and enjoy the abundant waters near Maryland’s Chesapeake Country Scenic Byway by sailing, kayaking, canoeing, cruising, or participating in a fun-filled waterfront celebration. Mark your calendar for the annual events and fill your summer days with exciting boating excursions on Chesapeake Bay and its tributaries.




