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Paddle Trips

Paddle one of our packaged trips along the Chester.
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Spring Cove: A Haven for Passing Ships

Spring Cove is indeed a welcome respite from the open waters of the Chester. Its protected nature makes for a calm paddle, just as this area was a safe harbor for ships that sought protection from the wind.

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A Paddle of Gratitude

Named for one of the steamboats used to ship goods and people across the Bay in the 19th century, this landing is a reminder of the importance of such technological advancements of the time. Paddle this area around Rock Hall and experience the shipping routes that were so important to this town's economy.

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Getting Bayside at Rock Hall Harbor

A prime put-in for paddlers who want to be in the midst of a bustling community is Bayside Landing. This area is popular with boaters and is chock-full of amenities such as marinas, bait shops, and restaurants.

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Allen’s Lane

Allen's Lane is an ideal launch site for paddlers wishing to get directly onto the Chester River without having to deal with the crowds found in Rock Hall. This is a site with access to smaller tributaries off the river, but Rock Hall Harbor is also fairly accessible from this point.

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Kent Narrows Public Landing

Kent Island bustles with activity, particularly during the summer at Kent Narrows. This site can be crowded but the adventure is well worth it to explore this area, which comprises the oldest European settlement in Maryland.

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Jackson Creek Landing, Gateway to the Queen’s Town

Located between Queenstown and Kent Narrows, Jackson Creek is a public beach on the Queen Anne's County side of the Chester River. Spend the day paddling the area or enjoy other forms of recreation such as fishing and crabbing.

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A Landing for Ferries on Rock Hall Public Beach

Rock Hall Public Beach, or Ferry Park as it is locally known, is an excellent choice for launching kayaks or canoes into the Chester River, for paddling to more protected tributaries north of the landing, or just for enjoying the vistas and the sunset over the Chesapeake.

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Green Lane

Rock Hall Harbor was a busy port that connected the eastern shore to major cities along the east coast, especially during the American Revolution. Launch from Green Lane and paddle through this economically and historically important harbor on your way to the wide Chester River, or calmer tributaries located just north.

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Bogle’s Wharf: A Paddle Fit for a Bird Enthusiast

Explore the more than 2,000 acres of Eastern Neck Island from the water, and keep an eye open for birds: this wildlife refuge provides habitat for more than 240 species of bird throughout the year.

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A Peaceful Paddle at “Graves End”

Though the origin of the name of this creek is debated, its popularity as a launch site is not. Grays Inn offers several miles of creek to explore, and also offers excellent crabbing in the spring and fall.

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Skinners Neck and the Shipbuilders of the Eastern Shore

In the 18th century, Grays Inn Creek was the site of one of only a handful of major shipyards on the eastern shore. Put in at Skinners Neck to explore the area where this economically-important shop once stood and enjoy the scenery as you go.

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Harrington Park Road

Paddle through quiet residential Kent County from the small launch at Harrington Park Road. Parking is limited, but opportunities for a gentle paddle are plentiful.

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A Long History of Watermen at Long Cove

At Long Cove, you'll be launching into an area highly trafficked by the working watermen of Kent County. Paddling down Langford Creek into the lower Chester River means you'll be in higher salinity water, and as a result, directly above excellent crabbing grounds.

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Shipyard Landing

This area is known to have been inhabited by Native Americans for years before European settlement. Explore the area by water by putting in at Shipyard Landing.

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Exploring “Porcupine Quills” Island from Broadneck Road

Broadneck Road's landing is ideally located between several points of interest to paddlers. For a day trip, spend some time exploring either the east or west fork of Langford Creek, or both. Cacaway Island is also not too far away and begs to be explored.

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Stepping into History at Centreville Public Landing

Stop in at Centreville to get off the wider Chester River onto one of its smaller tributaries, the Corsica River.

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Cliff City and the Living Shorelines of Conquest Beach

Explore the Chester River, the more serene Langford Creek, or the unique area of Conquest Beach and Preserve all from the landing at Cliff City.

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A “Convenient” Paddle at Quaker’s Neck

Quaker Neck is notable for offering beginner-friendly paddling options at Shippen Creek or Jarrett Creek, or a more adventurous paddle in the Chester proper for those looking for more of a challenge.

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Southeast Creek and the Church on the Hill

Southeast Creek offers a great location from which to explore quiet creeks and tributariesr, while still being in close proximity to prime crabbing grounds of the Chester River.

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Wilmer Park: Highway to History

Wilmer Park is the perfect place from which to explore historical Chestertown. With a picturesque waterfront park with convenient access for paddlers to get right on the water, this site has plenty of amenities and a beautiful waterway to explore and experience all the area has to offer.

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Cannon Street: Revisiting the Customs of the Colonies

Launch from this floating dock and experience one of the country's best preserved colonial seaports from the river that once served as its highway. Chestertown is full of history and scenery to explore by land or by water.

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Stopping for a Drink on Morgan Creek

Morgan Creek was at one point the site of several mills, as well as a brew pub that shipped ale to port towns like Chestertown. The lower part of the creek is a popular site for local fisherman.

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The Mills on Morgan Creek

Paddling from Riley's Mill on Morgan Creek is a unique opportunity to experience firsthand what was once a busy shipping route for grain.

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Bald Eagles Abound at Buckingham Wharf

For a calm day of paddling through eastern shore scenery, with the added potential of some excellent birdwatching, Buckingharm Wharf makes an excellent choice.

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Paddling the Farmlands of Deep Landing

Launching at Deep Landing will take paddlers on a tour through the all-important eastern shore economic staple, farmlands.

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Put in Your Bid at Crumpton Public Landing

As one of the last stops on a route of the great steamboat lines of the 19th and 20th centuries, Crumpton once anticipated much growth and development. Today this quiet town draws crowds every Wednesday for a more specific reason: the weekly Dixon Furniture Auction.

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Life’s a Peach at Shadding Reach

Shadding Reach lends itself to a quiet paddle among the farmland between the towns of Millington and Crumpton. With the introduction of railroads to the area, Millington soon became known for the peaches it shipped all over the county.

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Paddling the Head of the Chester at Millington

The town of Millington was named for the millhouse that still stands there and once milled grain for General Washington's troops. The millhouse and more can be seen on this quiet paddle.

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Paddle Notes

Trip ideas, how-to's, trip reports and more from the Chester.

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Interested in other ways to have fun in the Chesapeake region? Visit Find Your Chesapeake!


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