Suggested Trip

A Beautiful Eastern Shore Paddle and Visit to a Town with a Secret History


Some of my favorite things to do include paddling, bicycling, getting out in nature and seeing local history.  In April 2022, I put this all together for a day of exploration and adventure in the area around Sharptown, in Wicomico County, Maryland.  It was a beautiful spring day that ended up being both fun and educational.

Sharptown was built by the Nanticoke River and established as a shipbuilding town around 1769.  Named after the Nanticoke Native American Algonquian people, this deep river proved valuable for industrial transportation.  Though much of it is dredged today, I still find many of its tributaries deep, which, combined with its heavily forested and largely undeveloped shoreline, makes it an ideal place for paddling.

My wife, dog, and I launched our kayak and stand up paddleboard (SUP) from the boat ramp at Cherry Beach Park, then crossed the Nanticoke River to Dorchester County and paddled upstream for a mile.  At a very prominent duck blind, we entered Gales Creek.  Before arriving, I studied satellite photos and chose this waterway because it looked narrow enough to make us feel like we were deep in nature, yet wide enough so that portaging would not likely be required.  The latter concern turned out to be moot,  since sawblade cuts on some of the downfalls indicated that someone spent quite a bit of time keeping the waterway clear.

Paddling up Gales Creek with help from the flood tide, it didn’t take long before we spotted a northern water snake resting on a log.  We might have seen a lot more wildlife had it not been for the honking Canada geese that alerted the forest to our presence.

Northern water snake on Gales Creek

These waterfowl can be quite loud, but when the female incubates eggs, she lays low, trying not to draw attention.

Canada goose incubating eggs

Maryland has both a migratory and resident population of Canada geese.  The latter may be descended from a stocking dating back to 1935 when a group of 41 geese were relocated from the Midwest to Dorchester County.

I saw five beaver lodges on Gales Creek.  Beavers, the largest rodent in North America, build these homes which can be up to 20 feet wide and 10 feet tall.  On other tributaries of the Nanticoke, I have been able to hear the whining of young beavers inside a lodge, but on this day they were silent.

Kayaking past a beaver lodge

Many of the places I paddle are near marshes, meaning they are wetlands dominated by herbaceous plants such as grasses, rushes, or sedges.  In contrast, much of the area around Gales Creek is a swamp because it is a forested wetland.  I much prefer the latter because I find the scenery more interesting.  Some beautiful flora I found here include red maple, pinxter flower, and golden ragwort.

Red maple and caterpillar on Gales Creek

Pinxter flower on Gales Creek

Golden ragwort on Gales Creek

Kayaking on Gales Creek

We paddled upstream until we encountered a dam at mile 2.3, Galestown-Reliance Road. The dam backs up the creek to create Galestown Millpond, where largemouth bass, chain pickerel and bluegill are caught.  Some of its popularity with anglers may be due to the presence of its fish ladder, which provides a detour route for migrating fish past the dam. Known as Galestown, this area was once part of a deed dating back to 1714 called “Harpers Delight.”

Fish ladder under Galestown-Reliance Road

Below the dam, I found a few bluegill spawning beds created by the males for the females to release their eggs, which the males then fertilize and protect.

Back on the Nanticoke, the powerboat traffic picked up, so we played it safe by staying near the shore until we were across the river from our launch point.  Crossing the Nanticoke, we stayed close together to help ensure we were visible and didn’t impede boat traffic.  The round trip was an easy and scenic 4.6 miles with no portaging.

After loading up the watercraft and eating lunch, we unloaded the bicycles for the second half of our outing – a visit to San Domingo.  This is a place that you definitely need to learn about before you visit because the real beauty isn’t in what can be seen, but rather what has been done to create this proud, historic community founded by free Black pioneers that dates back to 1820.

We biked through Sharptown and then southwest on Sharptown Road (Route 313), which is flat, has a wide shoulder, and is lightly traveled, making it well suited for cycling.  At Cooper Mill Road (Route 461), we turned east and rode into San Domingo.  The town’s origins are largely based on the “Act Prohibiting Importation of Slaves,” a federal law promoted by President Thomas Jefferson which took effect in 1808.  The law banned the importation of enslaved peoples from Africa, driving up the price of slave labor on southern plantations.  This fueled the Reverse Underground Railroad, where both fugitive enslaved persons and free Blacks were kidnapped, transported to slave states, and sold as enslaved people.  San Domingo, just two miles south of Sharptown, became a refuge where free Blacks could live and work together in a mostly self-sufficient community that remained hidden from outsiders.

The town’s name is likely tied to the 1791-1804 Haitian Revolution, an anti-slavery insurrection by slaves against French colonial rule in Santo Domingo, a name that instilled fear in slave-holding communities.  Many of San Domingo’s founders, like James Brown, were from Haiti or descended from Haitian mariners, so it is believed that they chose a name similar to Santo Domingo to keep outsiders away.

We biked on some small, and sometimes unpaved, roads past San Domingo Park on the south side of town, and then north to San Domingo School, a yellow, two-story schoolhouse restored in 2004.  Previously known as the Sharptown Colored School, it was built in 1919, partly with funds donated by Julius Rosenwald, President of Sears, Roebuck, and Company.  Rosenwald, a first-generation Jewish American from Chicago, and Booker T. Washington worked together to build more than 5,000 schoolhouses in Black communities across the South between 1912 to 1932.  Today, this building serves as the San Domingo Community and Cultural Center.

Daphne on the steps of San Domingo School

Our next stop was the Zion United Methodist Church, where the town’s origins were recognized at their April 2022 Founders Day Service.  Constructed in the 1850s, the building burnt down in 1979 but was rebuilt thanks to the leadership of a white preacher from Sharptown.

Zion United Methodist Church in San Domingo

Walking through the adjoining cemetery, we looked at various tombstones, many with the family name of Brown or Quinton.  Naturally, the oldest were also the least legible, but we did find a few that were in excellent condition.

Tombstone of Mary P. Brown, wife of Leonard Brown.  Died January 11, 1877

Bicycling north on San Domingo Road (Route 477), we headed back to Sharptown via Laurel Road (Route 348), completing an easy and leisurely 17-mile circuit ride.

Pulling Daphne in her bicycle carrier on San Domingo Road

Prior to my dual adventure, I had never heard or read anything about paddling on Gales Creek.  This turned out to be a delightful and surprisingly navigable route.  Bicycling through San Domingo was also enjoyable, and up until 2021, it too was also relatively unknown.  I left the area that day with my “sense-of-adventure bucket” full, and feeling like I became privy to information only known by locals – secrets around Sharptown.

For more information see
Living Places – Sharptown Town
Paddle the Nanticoke
The Nanticoke River – Explorers Welcome
Bay Journal – A river less paddled: morning on the Upper Nanticoke
Visit Dorchester – Galestown
National Oceanic and Atmospheric Administration - What is a fish ladder?
Bay Journal – Saving San Domingo
National Archives – The Slave Trade
Wikipedia – Reverse Underground Railroad
Maryland’s National Register Properties – San Domingo School
The Incredible True Story of How Booker T. Washington & the President of Sears Built 5,000 Schools for Generations of Southern Black Students

Nanticoke River Water Trail

The Nanticoke River Water Trail offers excellent opportunities for paddlers to explore its history and beauty and to catch a glimpse of the wildlife that call it home.


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, beekeeping, and looking for new adventures. Saki's World is a great source of information about all these activities.

June 4, 2022

Main image: Saki and Daphne on Gales Creek in front of the Galestown Millpond dam. All photos by Saki.
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