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Suggested Trip

Tilghman Island – Paddling in Waterman Country


A note about COVID-19 and visiting parks: Help stop the spread of COVID-19 and follow all current directives from your governor and local health officials about wearing face masks and physical distancing.

I am not a native Marylander, but I have grown to love the Old Line State and the things that make it unique, such as its historic waterman towns.  Most have transitioned away from their roots, built museums, redeveloped their waterfront areas, and promoted tourism honoring their past.  But one place in particular, Tilghman Island, still embraces a very active waterman culture.  Some might say the heart of the island lies on the north end at Dogwood Harbor, home of the last working fleet of skipjacks in North America and one of the few harbors in the Chesapeake Bay where workboats clearly outnumber pleasure craft.  I was part of the latter when I launched my standup paddleboard (SUP) from the boat ramp and found myself beside about a dozen deadrise workboats, each ready to head out into the Bay to harvest crabs, oysters, clams, rockfish, and a variety of other seafood.

Skipjack Rebecca T. Ruark

I paddled about a quarter mile out to get a look at Avalon Island, which was built of discarded oyster shells.  The seafood industry on Tilghman Island reached its peak during WWII when the Tilghman Packing Company operated around the clock and almost everyone on the island participated in some way.  Skipjacks, Maryland’s state boat, were the main workboat for harvesting oysters.  As many as 2000 of these single-masted oyster dredgers were built in the area prior to WWII, but as of 2003, there were fewer than a dozen in operation, and today not more than five still dredge commercially.  Paddling near Avalon Island, I saw Rebecca T. Ruark pass by.  Dating back to 1886, this is our country’s oldest skipjack and is currently used for sailing charters.

Paddling north, I came to Knapps Narrows, the waterway that separates Tilghman Island from the Bay Hundred peninsula.  Here, a 124-foot-long drawbridge connects the two land masses.  Installed in 1998 and reportedly among the busiest drawbridges in the world, the Knapps Narrows (aka Tilghman Island) drawbridge replaced a similar one dating back to 1934, which now spans the entrance to the Chesapeake Bay Maritime Museum's parking lot.

Knapps Narrows drawbridge    

On the west side of Knapps Narrows, about a mile from Dogwood Harbor, I explored a group of small islands collectively referred to on some maps as Anne Arundel Island.  Paddling between wetland grasses on the marshy east side, I came upon something splashing around in some shallow water.  At first I thought it was a carp or ray, but when it leapt out of the water, I realized it was two river otters.  Seeing me, they ran across a narrow spit of land and jumped in the water on the other side.

River otters near Anne Arundel Island 

Paddling south on the west side of Tilghman Island, I passed Paw Paw Cove, an important archaeological site protected by the Eastern Shore Land Conservancy.  Here, some of the oldest stone tools in North America have been found – possibly over 13,000 years old!  Although it is commonly believed that the ancestors of Native Americans crossed the Bering Strait land bridge after the last ice age around 10,000 years ago, discoveries at Paw Paw Cove and similar sites have led some anthropologists to believe the Americas were first inhabited by Europeans, possibly arriving in boats.

Cownose rays near Sharps Island Lighthouse    

My favorite part of Tilghman Island, Blackwalnut Point, is at the southernmost end.  The waters around the point are home to an abundance of cownose rays that I love to photograph via SUP.  With wingspans up to three feet, cownose rays are truly magnificent creatures to behold as they appear to effortlessly fly through the water.  Over the last few years, I’ve visited this area several times and often counted several dozen in a single day, with the highest concentration in the three-mile stretch between Blackwalnut Point and Sharps Island Lighthouse (built in 1882).  I expect their prevalence here has something to do with the fact that cownose rays eat some of the same shellfish for which Tilghman Island is known.  In 2006, these rays were blamed for the declining oyster population, leading to a campaign called “Save the Bay, Eat a Ray.”  But ten years later, studies have shown that oysters do not comprise a high percentage of their diet, and that the oyster decline did not correlate with the increase in ray population.

Osprey in nest with juvenile laying low at Blackwalnut Cove    

It is a long trip from Dogwood Harbor to Blackwalnut Point (3.5 miles) and even further to Sharps Island Lighthouse (6.5 miles).  Fortunately, there are launch sites at the southern end of Tilghman Island that make both places more accessible.  My favorite is Bar Neck Landing (21560 Bar Neck Cove Road, Tilghman, Maryland), which puts one on the east side of the 3.5-mile long Blackwalnut Cove Water Trail.  Here, one can paddle southwest across Blackwalnut Cove to the scenic 53-acre Black Walnut Point Natural Resources Management Area, where over 225 bird species have been reported.  Unlike most of the island, Blackwalnut Cove is fairly protected and therefore better suited for less experienced paddlers or windy/inclement weather.     

Pulling back into Dogwood Harbor, I saw skipjacks Hilda M. Willing (built 1905) and Thomas W. Clyde (built 1911), both moored near a sign that read "Skipjack docking only"…probably the only place I will ever see such a sign.  It made me think about the waterman lifestyle celebrated annually at Tilghman Island Day, which hosts activities such as an anchor throw, boat docking competition, and crab picking contest.  Carrying my SUP from the ramp, I felt thankful to have been given the opportunity to spend the day in the heart of waterman country.

For more information, see
Tilghman Island and the Bay Hundred Water Trails
Tilghman Island Water Trail
Environment Maryland – Waterman Blues
Bay Dreaming – Tilghman Island, Maryland
The Last Skipjacks Project
Bay Journal – Tilghman Island arrowheads may point to Bay’s earliest visitors
Chesapeake Bay Program – Cownose Rays
Florida Museum - Rhinoptera bonasus
National Aquarium - Where 'Save the Bay, Eat a Ray' Went Wrong
MD Birding Guide - Black Walnut Point Natural Resources Management Area

Dogwood Harbor at Tilghman Island

Dogwood Harbor brings to life tradition, heritage and the work ethics of Chesapeake Bay watermen. Visitors can communicate with multi-generation watermen and learn about the Bay aboard an authentic skipjack.


Saki has been exploring the Chesapeake Bay and its tributaries on kayak or stand up paddleboard (SUP) since 1999. He has competed in various races, organized and led numerous trips, and circumnavigated Kent Island both via kayak and SUP. Saki also enjoys nature photography, hiking, cross country skiing, raising chickens, and looking for new adventures.

December 5, 2019

Main image: Deadrise workboats at Dogwood Harbor. All photos by Saki.
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