Exploring the Chesapeake Bay by Paddle: Top Kayaking and Paddleboarding Adventures

Maryland’s Eastern Shore is a paddler’s paradise, with its intricate network of rivers, creeks, and inlets winding toward the Chesapeake Bay. Few experiences rival the peace of gliding across the water with only the sound of a dipping paddle and the occasional call of a native bird overhead. Whether you’re a seasoned kayaker or a first-time paddleboarder, the region offers stunning waterways to explore, from secluded inland trails to vast, open waters.

For those based in Salisbury, MD, or nearby, there’s no shortage of paddling opportunities. Whether you’re looking for a peaceful wildlife tour or an adventurous trek along historical waterways, here are some of the best kayaking and paddleboarding destinations the Eastern Shore has to offer.

Pocomoke River: A Journey Through the Blackwater Swamp

The Pocomoke River is one of Maryland’s most iconic paddling destinations, flowing from Delaware through Salisbury, MD, before emptying into the Chesapeake Bay.

For beginners, the stretch between Snow Hill and Porters Crossing is a great introduction, offering calm waters and a chance to see river otters, turtles, and great blue herons. More experienced paddlers can venture farther downstream, where the river widens and takes on a different character before merging with the Bay.

Blackwater National Wildlife Refuge: A Haven for Birdwatchers

Located near Cambridge, the Blackwater National Wildlife Refuge is a paddler’s dream. With expansive marshlands and glassy waters, this area is home to bald eagles, egrets, and migratory waterfowl. The winding trails of the Blackwater River and Transquaking River offer a peaceful, scenic experience, ideal for those looking to combine kayaking with wildlife photography.

Guided eco-tours are available for those who want expert insight into the refuge’s delicate ecosystem. Be sure to bring binoculars, as this is one of the best places on the East Coast for spotting birds in their natural habitat.

The Choptank River: History Meets Nature

For a paddle steeped in history, the Choptank River is a must. This waterway is part of the Captain John Smith Chesapeake National Historic Trail, following the same route taken by early explorers and Indigenous peoples. The upper Choptank and Tuckahoe Rivers feature calm waters perfect for a relaxed outing, while the lower sections open up to stunning views of the Chesapeake.

Launching from Denton or Greensboro provides access to miles of peaceful paddling, where you can pass historic steamboat wharfs and wooded shorelines.

Tilghman Island: Coastal Paddling at Its Best

For those looking to venture closer to the Bay itself, Tilghman Island offers incredible paddling routes. The sheltered Blackwalnut Trail is perfect for beginners, weaving through quiet coves and tidal marshes. More experienced paddlers can explore Knapp’s Narrows, where working watermen haul in fresh seafood, or head out into the Bay’s open waters for a challenge.

Sunsets here are breathtaking, and for those wanting a longer adventure, nearby overnight accommodations make it easy to turn a day paddle into a weekend escape.

Assateague Island: Paddle Among the Wild Ponies

One of the most famous destinations for paddlers in the region, Assateague Island provides a chance to paddle along untouched beaches, winding creeks, and salt marshes full of wildlife. The highlight is spotting the island’s famous wild ponies grazing along the shoreline.

Paddlers can launch from Chincoteague Island in Virginia or from the Maryland side near Berlin. While the water is usually calm in the sheltered areas, conditions can change quickly in open waters, so checking tides and weather before heading out is crucial.

Finding Your Next Paddling Adventure

Whether you’re navigating the cypress-lined Pocomoke River, spotting bald eagles at Blackwater, or paddling alongside wild ponies at Assateague, the Chesapeake’s diverse waterways offer something for everyone. With so many incredible places to explore, those in Salisbury, MD, are lucky to have some of the best paddling destinations right in their backyard.