Participants in last year's Bay Paddle raced 45-miles from Rock Hall to Cambridge, Maryland to support clean water initiatives. Photo courtesy of Eastern Shore Drone Photography

Traversing the Bay, Top to Bottom

The Chesapeake Bay watershed is a paddler’s paradise. Whether you thrill at the whitewater rapids of her Western Shore tributaries as the streams tumble down Appalachian mountainsides or prefer to drift through the serene marshes of the Eastern Shore, you’ll find a lifetime of places to explore by kayak, canoe, standup paddleboard or whatever craft you can propel under your own power. The possibilities are virtually endless. Here are some places to start.

I have a unique perspective on the Chesapeake Bay. On Sept 26, 2021, I completed a nine-day, 207-mile adventure standup paddling its entire length from Havre de Grace to the Atlantic Ocean to help raise money for Oyster Recovery Partnership. 

It was both a grueling effort and an unforgettable experience that filled me with more appreciation for the beauty of the Bay and put me on a mission to leave it better than I found it. 

We’re so fortunate to have the Bay in our backyard providing some of the most picturesque paddling in the world. I’ve paddled with dolphins, watched eagles soar above, surfed some Bay rollers, paddled near historic towns and been taken back to a time when the Chesapeake was run by shoremen. 

Any day on the water is a good one and there are hundreds of great paddling spots on the Bay. I’ve highlighted below some of my favorite destinations and how to best enjoy them.

Havre de Grace represents the diversity of the Bay. The water is crystal clear to 10 feet or more. You almost feel like you could reach down and grab fish from the grasses underneath. It’s hard to believe you’re on the same body of brackish, murkier water found farther south. The Eastern Shore seems to rise like a mountain on the opposite side. The whole experience is like paddling a lake. 

Concord Point Lighthouse is a great launching point. There’s parking and a public pier with a ramp down to the water. Start at high tide. There’s a large reef of grass that’s like paddling through mud when it’s low tide. The reef extends from the shoreline about half a mile out. Head straight towards the Eastern Shore, then south and around the Susquehanna National Wildlife Refuge, a small island just north of Aberdeen. You should get a nice little push from the Susquehanna River flowing into the Bay. If you need a little extra motivation, treat yourself to Bomboy’s Homemade Ice Cream after you get back to shore. 

Rock Hall might be the nicest harbor on the Bay. It’s well-protected from any wind and has great waterfront restaurants, natural surroundings and minimal boat traffic. You can go in any direction once you’re out of the harbor or just enjoy paddling around Rock Hall. 

Chris Hopkinson and a cruising companion on their 207-mile paddle down the entire length of the Chesapeake Bay. Photo courtesy of Katie Sheridan

Launch from Green Lane Boat Ramp next to Haven Harbour South. You might not want to leave Haven Harbour once you’re there. They have a great beach with fire pits, a restaurant and a kayak launch. You can go south on the Bay out of Rock Hall towards Eastern Neck Wildlife Refuge, about 6 miles one way. Or head north about 2.5 miles and head into Swan Creek, another well-protected harbor on the other side of Rock Hall. 

Wye Island is like paddling in a national park. It’s 14 miles to circumnavigate the entire island and 5 if you go just past the Wye Island Road bridge and back. You’ll see plenty of wildlife along the way and likely no one else. It’s also mostly protected from any wind direction, so you’ll rarely have any chop. You can try a paddle and hike or picnic. Wye Island comprises 2,800 acres with hiking trails throughout. Check out the trail map online, paddle up to one of the trails with beach access and explore or just relax. Launch from Wye Landing boat ramp. There’s a small beach area on the left hidden by some grasses where you can walk into the water. 

The Honga River is one of the few places on the Bay where time seems to have stood still. You enter via Fishing Creek, passing under the Hoopers Island Bridge as if the bridge itself is your gateway to the past. The river is serene with birds, living shorelines, small beaches and virtually no boat traffic. There’s a quiet solitude to the Honga that brings you back to the Bay’s past. 

You can do a nice 9-mile loop circumnavigating Upper Hooper’s Island starting and finishing at Tylers Cove Boat Ramp. You’ll pass Old Salty’s as you paddle around Hoopers Island on the Bay side. Head back there to enjoy the views and a well-deserved snack and beverage after your paddle.

We’re heading a little farther south for this one, but it’s well worth the trip. Have you ever paddled around sunken ghost ships? Well, here’s your chance. Kiptopeke State Park in Virginia is home to a fleet of partially sunken concrete WWII supply ships that lie right off the beach. There’s a story behind why they used concrete for the ships and how they ended up in the Bay. I encourage you to explore the ships and their history.

Ghost ships aren’t the only attraction on the southern Eastern Shore. Cape Charles is a true beach town on the Chesapeake. It has historic homes with wraparound porches, shops, a great brewery, one of the largest public beaches on the Bay and is entirely golf cart friendly. It’s a can’t-miss weekend destination even if you’re not paddling. 

My 200-plus-mile route down the Bay was along the Eastern Shore, so it’s hard for me to not be biased about its beauty. However, I trained along the Western Shore and Jonas and Anne Catharine Green Park in Annapolis was one of my favorites. 

I look for three things when seeking out a new paddle spot: parking, a beach launch and cool things to see along the shoreline. Jonas Green checks all three, plus paddling under a large bridge is always fun. Jonas’s parking lot gets crowded, so get there early. Paddle up the Severn River towards the bridge and make your way to St. Helena Island. It’s just over 11 miles roundtrip and offers a unique real estate tour. You’ll pass some incredible waterfront homes and neighborhoods such as Sherwood Forest. Refuel after your paddle with a breakfast burrito from Rise Up in the Annapolis Market House. 

Nothing beats being on the Bay. You feel both connected to its beauty and disconnected from everything on land. That’s why we all enjoy it as much as we do. I still get goosebumps just looking at it as I drive over the Bay Bridge. So get on the water, invite others to join you, explore and do what you can to leave the Bay better than you found it. 


Chris Hopkinson is the founder of Bay Paddle, an annual paddle race celebrating the Bay and benefiting Oyster Recovery Partnership, Waterkeepers Chesapeake and Chesapeake Conservancy. The race has raised nearly $400,000 in three years.