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By far, the feature that has played the largest role in defining the land, culture, and history of the Upper Eastern
Shore is the Chesapeake Bay. The bay holds a mythic significance as Provider, Connector, and Playground. The bay has provided settlers of this shore, ancient and modern, with fish, fowl, oysters, and
crabs. As connector, the bay and its many navigable rivers allow easy access to local settlements and ports around the world. As playground, the bay provides ample opportunities for pleasure-seekers to
ply the waters in an infinite variety of craft.
The bay and its rivers are full of life, and humans have developed a great many ways to get on the water to harvest this
abundance. Most notable among the Chesapeakeâs unique watercraft are the skipjacks, bugeyes, and log canoes. With a shallow draft and low gunwales, the skipjack, like the bugeye, is ideally suited for
dredging oysters from the shallow beds just off shore. Log canoes are early sailing vessels built for speed to get the waterman to the oyster beds and crab pots before his rival.
Just as the regionâs boats were uniquely suited for life on the bay, so too are the people who ply its waters.
Watermen--those who harvest the bay and spend more of their time on the water than on land--have been a feature of the Upper Eastern Shore since the first colonial settlements. In particular, during the late
nineteenth century, fishing and oystering became a major industry, and watermen were in demand. The culture flourished and hundreds of skipjacks roamed the water searching for the best oyster beds. Today,
there are fewer than twenty surviving skipjacks. The largest fleet anchors at Dogwood Harbor on Tilghman Island.
By the late nineteenth and early twentieth century, other boats became a frequent sight on the water. Steamboats crossed
the bay transporting agricultural goods to the western shore and tourists to the eastern shore. The Choptank and Tuckahoe Rivers are lined with steamboat landings. Fresh and canned agricultural products were
loaded onto steamboats as far upriver as Denton and Greensboro. Love Point at the northern tip of Kent Island was a famous steamboat landing, bringing pleasure seekers from Baltimore to a train that took them
to resorts in Ocean City on Marylandâs Atlantic coast.
The steamboats have stopped sailing, but annually, thousands of people come to the Upper Eastern Shore by boat to enjoy
its ageless pleasures. The shore is lined with marinas for everything from multi-million-dollar yachts to simple catamarans. Yacht clubs from Chestertown to Denton hold regattas throughout the
year. In addition, there are many opportunities for the public to get on the water at public landings or by renting canoes, small sailboats, sea kayaks, or jet-powered craft.
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