The Chesapeake City Bridge crosses over the C&D Canal and provides views of the city below.

The Chesapeake City Bridge crosses over the C&D Canal and provides stunning views of the city and canal.

Chesapeake Water Trails

Explore the mighty Chesapeake with the power of your paddle or the wind in your sails.

The Chesapeake City Bridge crosses over the C&D Canal and provides views of the city below.

The Chesapeake City Bridge crosses over the C&D Canal and provides stunning views of the city and canal.

There are so many ways to experience the wonder of The Chesapeake Bay, but none get you closer to this magical estuary than Maryland’s amazing water trails. Wending their way through pristine marshlands, skirting historic shores, or even setting out over the broad expanse of the bay, Maryland’s water trails can be perfect for first time paddlers on up to experienced sailors and even power boaters. Take the plunge into our list of Chesapeake Water Trails and find the route for you.

The Captain John Smith Chesapeake National Historic Trail, Chesapeake Bay
Kayaking at the Capt. John Smith Trail at Piscataway Park
Accokeek Foundation

Tracing 3,000 miles and 15,000 years of culture and history, the Captain John Smith National Historic Trail is the ultimate way to experience the bay. Named for the first European to explore the Chesapeake Bay, and a living tribute to the indigineous peoples of Maryland, this one-of-a-kind adventure promises the experience of a lifetime. Explore by powerboat or sail, or chunk it up for a lifetime’s worth of paddling adventures. However you hit the water, you will never forget your time on the Captain John Smith Chesapeake National Historic Trail.

Janes Island State Park Water Trails, Lower Eastern Shore, Crisfield
Janes Island is an ideal spot for watersports like kayaking.

Perfect for paddlers of every skill level, there’s so much Eastern Shore adventure to choose from at Janes Island State Park. Seven marked trails cover more than 30 magical miles, all beginning at the park’s marina and boat launch. Experience this saltmarsh ecosystem up close with routes along Tangier Sound, the Big and Little Annemessex Rivers, and more!

Fishing Bay Water Trail, Lower Eastern Shore, Dorchester County
On the water at sunset in Dorchester
Jill Jasuta Photography

Looking to test your paddling mettle? The Transquaking River Loop and Island Creek Trails aren’t marked, and you may not see another soul on your journey, adding a sense of adventure for paddlers willing, able and equipped to travel by map. And the rewards are great! Kayak through iconic Eastern Shore-scapes of idyllic creeks, marsh habitat, secluded ponds, and islands of loblolly pine.

Nanticoke River Water Trail, Lower Eastern Shore, Dorchester & Wicomico Counties
Nanticoke River

Running the 64-mile length of the meandering Nanticoke River, with easy access at more than 25 public launches, boat ramps, and piers, the Nanticoke River Water Trail is a unique escape. Home of the largest concentration of bald eagles in the North East, marvel at these mighty raptors soaring above, and use the trail to visit towns along the way with museums, dining, and even shopping adventures. Find out more at or get the map at the Dorchester County Visitor Center and through the link to the DNR Outdoor Store.

Blackwater National Wildlife Refuge Paddling Trails, Lower Eastern Shore, Church Creek
Blackwater National Wildlife Refuge at Sunrise

With nearly 50 square miles of forests, fields, marshes and open water, Blackwater National Wildlife Refuge, “The Everglades of the North,” offers breathtaking vistas and a rare glimpse of untouched America.

The Blackwater is simply a must experience for any lover of the outdoors. Open vistas, winding marshes, and remarkable wildlife viewing at the heart of the Great Atlantic Flyway have earned The Blackwater its nickname, “The Everglades of the North.” Beginners are invited to the Green Trail, with the Purple Trail fit for more seasoned paddlers and, as always, check ahead for weather and other advisories, but do not miss this truly special place.

Smith Island Water Trails, Lower Eastern Shore, Ewell
View of Smith Island from the water

Iconic Smith Island, a watermen community in the heart of the Chesapeake, reachable only by boat, also offers unparalleled paddling adventures. Seven marked trails vary in length from 1 to 4.4 miles. The water trails explore the island’s 8,000 acres of marsh and access the island’s three villages. For the experienced paddler with the right boat, explore vast expanses of open bay and bring home memories that will last a lifetime.

Monie Bay Water Trails, Lower Eastern Shore, Deal Island
Deal Island
carriesassafras - Instagram

Three trails explore this remarkable place, part of the Chesapeake Bay National Estuarine Research Reserve, set within the idyllic Deal Island Wildlife Management Area (WMA). The WMA is more than 13,000 acres of tidal marsh, peaceful forested wetlands, thrilling open water, and a 2,800-acre man-made pond. Monie Bay offers amazing wildlife viewing, along with fishing, hunting, hiking and paddling adventures for every skill level.

Kent Island Water Trails, Middle Eastern Shore, Kent Island
Kent County

Just on the eastern side of the Bay Bridge you’ll find six varied water trails exploring historic Kent Island. Choose a secluded, sheltered trail, or set your paddle to the big waters of the Chesapeake Bay, Chester River, Eastern Bay, and Prospect Bay.

Tilghman Island and Bay Hundred Water Trails, Middle Eastern Shore, Talbot County
Boat on Tilghman Island

Five mapped trails range from an easy mile to a more ambitious 5.2 miles in length. GPS points guide your way through the heart of the shore. See amazing wildlife including vast flocks of migrating ducks and geese, majestic eagles, and find excellent fishing along the way. Get the map from the Talbot County Office of Tourism in Easton.

Corsica River Water Trails, Upper Eastern Shore, Centreville
Corsica River
Corsica River Conservancy

Centreville was once the launch site for grains that were shipped to feed George Washington’s armies during the Revolutionary War. Today, the Centreville Wharf and Centreville Landing mark the starting points for four water trails. The Mill Stream and Yellow Bank Stream trails pass through calm, low marshes and make for peaceful easy paddling, while the Alder Branch Trail heads out into the main waters of the Corsica River with its stronger currents and open stretches.

Marshyhope Creek Water Trails, Middle Eastern Shore, Federalsburg
Marshyhope Creek
Nathan Bolduc/Bridgehunter

 Paddle out from the Federalsburg Canoe and Kayak Launch, the site of the Annual Frog Fest, which is celebrated on the last Saturday in June. Surrounded by small town charm and more than 3,000 acres of wildlife preserve, it’s the perfect spot to launch a serene river paddle.

Eastern Neck Island Water Trail, Upper Eastern Shore, Eastern Neck Island
Eastern Neck National Wildlife Refuge

Ten miles long and circumnavigating the island wildlife refuge, Eastern Neck is home to diamondback terrapins, great flocks of migrating waterfowl, and the ever present osprey and herons that dot the sky. Beginning in the relative shelter of the Chester River, this trail can carry adventurers out into the main waters of the Chesapeake Bay. The Eastern Neck Island Water Trail is not for novices, but is frankly stunning, and for the most athletic, it comes with the satisfaction of making the trip all the way around the island.

Chesapeake Bay Environmental Center Water Trails, Upper Eastern Shore, Grasonville
The Chesapeake Bay Environmental Center offers educational experiences, hiking, kayaking, paddleboarding and birding.

The Chesapeake Bay Environmental Center offers educational experiences, hiking, kayaking, paddleboarding and birding.

You can rent a kayak right at the Chesapeake Bay Environmental Center (CBEC) and head out onto their three amazing water trails, ranging from just a mile to 2.8 miles. Paddle through marshy wetlands and tree-lined woodland habitats. CBEC was founded by The Wildfowl Trust of North America and is a great spot to see eagles overhead. 

Patuxent River Water Trail, Southern Maryland
Patuxent River

The beautiful Patuxent River flows more than 100 miles with dozens of launches along its luxuriating banks, inviting day paddlers to pick a portion, or true adventurers to plan a canoe-camping getaway. Highlights include the picturesque Jug Bay Natural Area, Sotterley Plantation, and the famous Calvert Marine Museum.

Potomac River Water Trail, Southern Maryland
Dock on the Capt. John Smith Trail at Piscataway Park
Accokeek Foundation

The Mighty Potomac, flowing through the cradle of our history, is a dedicated American Heritage River and a National Recreational Trail. With stunning spots along the way, from the happening shores of National Harbor to the quiet waters of Mallows Bay National Marine Sanctuary with its famous ship graveyard, and on to the mouth of the great Chesapeake Bay, there are endless opportunities for paddling adventure along its length.

The Mattawoman Creek Water Trail, Southern Maryland, Indian Head
Mattawoman Creek during Bassmaster Elite and Discover Quest
Charles County Tourism

This trail combines sheltered water on the Mattawoman that is perfect for new paddlers with a loop out into the Potomac for those ready for adventure. Explore the beautiful forested shores of the Mattawoman Natural Environment Area for incredible birding, and see the legendary ospreys of Smallwood State Park.

Mallows Bay & the Lower Potomac River Water Trail, Southern Maryland, Charles County
decayed ship
Don Shomette

Part of the larger Potomac River Water Trail, which runs from the Nation’s Capital to the Chesapeake, the Lower Potomac Trail is truly unique. Put in at Nanjemoy Wildlife Management Area and paddle up river to famous Mallows Bay National Marine Sanctuary, home of the largest ghost fleet of ships in the Western Hemisphere. Paddle among the hulls of mighty ships as they are reclaimed by the woods and wetlands of the river.

Friendship Farm Park Water Trail, Southern Maryland, Charles County
Mallows Bay Park
Ralph Eshelman

Kayak Mallows Bay with a guide to discover submerged shipwrecks that have created a protected fish nursery habitat. Look for waterfowl and aquatic life in this remote and natural paradise.

Explore rolling southern Maryland farm land and lush marsh ecosystems along Church Creek and Nanjemoy Creek. See marsh flowers in bloom, enjoy the amazing fishing, and even camp along this sheltered trail.

Port Tobacco River Trail, Southern Maryland, Port Tobacco
Chapel Point State Park in Port Tobacco along Port Tobacco River
Maryland DNR

Set out from the charming colonial town of Port Tobacco for a serene paddling excursion. Explore the shoreline of Chapel Point State Park, and even pitch a tent at Goose Bay Marina and Campground right along the banks. Find it all here.

Point Lookout Water Trails, Southern Maryland, Point Lookout State Park
Point Lookout beach

The mighty Potomac River and the great Chesapeake Bay meet at Point Lookout. This remarkable wildlife and recreation spot offers majestic views and intriguing history as the site of a Civil War prison camp. Three water trails, each about three miles in length, offer paddling excursions, ranging from just an hour or so to a full weekend with overnight camping in the park. Pick up a guide at the Point Lookout State Park Visitor Center.

Western St. Mary’s Water Trails, Southern Maryland, St. Mary’s County
The Maryland Dove sits anchored in St. Mary's City
KeithBurke_photography - Instagram

St. Mary’s County is truly a paddler’s paradise with six trails to choose from. Explore the waters around Historic St. Mary’s City, Maryland’s colonial founding place. Set out from Port of Leonardtown, a hip Arts & Entertainment District offering outdoor concerts, art galleries, special events and wineries. Find out about the lighthouses, museums, and more that you’ll discover in this great collection of water trails.