About the Chesapeake Bay Sailing Log Canoes
Chesapeake Bay log canoes began as working boats and evolved into some of the most distinctive racing vessels in American sailing. Their history is closely tied to the watermen, boatbuilders, families, and communities of Maryland’s Eastern Shore, including St. Michaels and the Miles River.
If you are planning to visit Saint Michaels (and you should), see if you can get a room at the Log Canoe Inn. Of course, Saint Michaels and the Miles River are famous for the Log Canoe races, which date back to the 1800s.
Jessica W. - on Google
History of the Chesapeake Bay Sailing Log Canoes
The Chesapeake Bay log canoe is one of the most unique and iconic sailing vessels in American maritime history. Originally built as working boats, log canoes were constructed from three to five logs carefully joined together to form the hull and keel. Watermen used these vessels for fishing, crabbing, and oystering throughout the Chesapeake Bay. During the 19th century, competition among watermen led to an unexpected evolution of the log canoe. Skippers racing back to shore with their daily oyster harvests soon realized that the first boat to reach the dock often received the highest price for its catch. As a result, larger sails were added and the boats became faster, eventually giving rise to the competitive sailing tradition that continues today.
Modern log canoes are renowned for their dramatic appearance and challenging sailing characteristics. Most surviving vessels are between 75 and 100 years old, with fewer than two dozen remaining in existence. Their narrow beams and oversized schooner rigs create an enormous sail area, making the boats exceptionally fast but also highly unstable and prone to capsizing. To counterbalance the force of the wind, crews use movable ballast in the form of long springboards that extend up to fifteen feet beyond the sides of the boat. Sailors perch on these boards, shifting their weight from side to side as the boat changes direction, helping to keep the vessel upright.
Watching a log canoe race is unlike any other sailing experience. As the boats tack across the water, crews slide down the springboards, move them across the deck, and climb back into position in a carefully choreographed motion. The teamwork, timing, and athleticism required to sail these historic vessels have become a hallmark of Chesapeake Bay racing culture. While their movements may not be graceful in the traditional sense, there is a remarkable rhythm and coordination to the process that has captivated spectators for generations.
Today, log canoes remain a treasured symbol of the Chesapeake Bay's maritime heritage and are celebrated through races and events held throughout the region each year. Their continued preservation is a testament to the dedication of owners, sailors, and communities who work to keep this unique tradition alive. As an old sailing adage reminds us: "If two boats are sailing the same course, there is a race going on—whether the other captain knows it or not."
The Log Canoes Honored at Log Canoe Inn
The Log Canoe Inn's six guest rooms are each named after historic log canoes that hold a special connection to our property, St. Michaels, and the Wilson family. While many other canoes continue to race and contribute to this living tradition, the vessels featured throughout the inn represent some of the stories, families, rivalries, and accomplishments that have helped shape Chesapeake Bay log canoe racing for generations. We are proud to share their history and help keep this extraordinary Eastern Shore tradition alive for future generations.
Mystery
Built in 1932 by master boatbuilder Harry Sinclair in nearby Oxford, Maryland, Mystery was originally constructed as a "secret weapon" intended to challenge the dominant racing canoe Flying Cloud in the prestigious Governor's Cup. The boat's purpose and design were kept closely guarded during construction, inspiring the name Mystery.
Measuring just over 34 feet in length, Mystery is known for her sleek lines, impressive speed, and towering masts. She is one of only a handful of surviving Chesapeake Bay racing log canoes, preserving a unique sailing tradition that has been a part of Maryland's Eastern Shore since the 1840s. In recognition of her historical significance, Mystery was listed on the National Register of Historic Places in 1985.
Over the decades, Mystery has undergone several transformations. After her early racing years, she was converted into a cruising vessel and sailed extensively throughout the Chesapeake Bay. In the 1950s, owner John Whittum returned her to racing form, eventually winning the Governor's Cup in 1962. Later, under the stewardship of Francis Schauber, the canoe underwent a major restoration and modernization, including the installation of an extraordinary 60-foot foremast—at the time the tallest mast ever carried by a log canoe of her size.
Today, Mystery continues to race under sail #8, and remains a symbol of the craftsmanship, innovation, and competitive spirit that define Chesapeake Bay log canoe racing.
Mary Rider
Built in 1877 on Tilghman Island by James Lowry, Mary Rider began her life as a working waterman's boat, a common origin for many of the Chesapeake Bay's historic log canoes. Originally known as Louise, she was named after Louise Kemp of Wades Point before eventually becoming the vessel remembered today.
By 1917, the canoe had been abandoned and left ashore on Fogg Beach in St. Michaels. There she was discovered by Captain William "Bill" Green, who recognized her potential and undertook the task of restoring her. After a complete reconditioning, he renamed the canoe Mary Rider in honor of his youngest daughter and returned her to the racing fleet. Under Captain Green's leadership, Mary Rider quickly established herself as one of the premier racing log canoes on the Chesapeake Bay.
Mary Rider's greatest achievement came when she captured the prestigious Governor's Cup for three consecutive years—1928, 1929, and 1930—a remarkable accomplishment that secured her place in Chesapeake Bay racing history. Captain Green's crew was made up largely of his five daughters, making the family an unforgettable presence on the racecourse. One of those daughters, Tunis Green, later married Captain George "Bob" Wilson, owner of the historic log canoe Magic. The close connection between the Green and Wilson families created a friendly but fierce rivalry, as the two families raced Mary Rider and Magic against one another for many years.
Although Mary Rider's final documented race took place in 1948, her legacy continues to live on through the stories, photographs, and traditions of Chesapeake Bay sailing.
Oliver’s Gift
Built in 1947 by renowned boatbuilder and naval architect Oliver Duke of Royal Oak, Maryland, the canoe measures 30 feet, 7 inches in length with a beam of 7 feet, 3 inches. Oliver’s Gift holds a special place in Chesapeake maritime history as the last log canoe built during the great revival of log canoe racing that began in the 1920s. Tragically, Duke passed away before the canoe was completed, and the vessel was finished by his nephew, Duke Adams, who continued the family’s boatbuilding tradition. Over the decades, Oliver’s Gift has earned a reputation as a successful competitor on the racecourse while serving as a testament to Duke’s skill as one of the Chesapeake’s most respected log canoe builders. Perhaps most remarkably, the canoe has remained in the same family since her construction, passing through generations of descendants who have carefully maintained and raced her, preserving not only the vessel itself but also the heritage, craftsmanship, and family legacy that make Chesapeake Bay log canoes so unique. Today, Oliver’s Gift stands as both a successful racing canoe and a living testament to the families who have dedicated themselves to keeping this iconic Chesapeake tradition alive.
Island Bird
Built in 1882 on Tilghman Island by master boatbuilder William Sidney Covington, the 27-foot canoe is among the oldest and smallest active racing log canoes still competing today. Raced under sail number 4, Island Bird has remained in the hands of Covington’s descendants for generations and has been a fixture on Chesapeake Bay racecourses for decades. The canoe became especially associated with the late Honorable John C. North II, Covington’s great-grandson, who skippered the Island Bird for nearly 70 years and won virtually every major log canoe trophy during his remarkable sailing career. Judge North, a respected Maryland jurist, environmental advocate, founding member of the Chesapeake Bay Maritime Museum, and author of Tradition, Speed and Grace: Chesapeake Bay Sailing Log Canoes, devoted much of his life to preserving the history and tradition of Chesapeake log canoe racing. Through the stewardship of the North family, Island Bird remains both a competitive racing vessel and a treasured symbol of the Chesapeake Bay’s enduring sailing culture.
Island Lark
Built on Kent Island in 1901, Island Lark was constructed with a singular purpose—to challenge and defeat Island Blossom, a rival log canoe built in 1892 by renowned boatbuilder Sydney Covington. More than one hundred years later, the rivalry between these historic vessels continues, making them two of the most recognizable and competitive boats in the Chesapeake Bay racing fleet.
For decades, Island Lark was skippered by Tad DuPont, one of the most respected figures in Chesapeake Bay log canoe racing. DuPont often described log canoe racing as the ultimate team sport, emphasizing the dedication and camaraderie of the crew. Some members of Lark's crew sailed together for more than 30 years, bringing together people of all ages and backgrounds who shared a common passion for preserving this unique Chesapeake tradition.
DuPont frequently noted that the level of competition in log canoe racing was unlike any other sailing circuit he had experienced. Despite being built over a century ago, Island Lark and Island Blossom continued to battle for victories, often finishing neck-and-neck at the front of the fleet. Their enduring rivalry is a testament to both the craftsmanship of the original builders and the dedication of the sailors who continue to race them today.
Today, the legacy of Island Lark continues through the next generation under the stewardship of Corey and Andrew Devlin. Guests staying in the Lark Suite may even have the opportunity to see the canoe launched from Higgins Yacht Yard & Marina as she prepares for regattas on the Miles River. The suite celebrates not only a remarkable racing vessel, but also the teamwork, tradition, and community spirit that define Chesapeake Bay log canoe racing.
Magic
Built in 1894 by Charles Tarr in St. Michaels, Maryland, Magic measures just over 34 feet in length and began her life as a commercial oystering vessel, working the waters of the Chesapeake Bay for nearly three decades.
In 1923, Captain George "Bob" Wilson purchased Magic for $100 and, alongside his close friend and renowned sailor Lowndes Johnson, transformed her from a working boat into a racing canoe. The conversion proved to be a tremendous success. Magic quickly established herself as one of the fastest boats in the fleet and earned her place in Chesapeake Bay sailing history by winning the inaugural Governor's Cup race in 1927.
The canoe remained in the Wilson family for generations. Captain Bob Wilson's son, George Wilson Jr., raced Magic throughout the 1960s and 1970s before passing the helm to his younger brother, James "Jimmy" Wilson. Jimmy became a well-known figure in the St. Michaels sailing community and skippered Magic until his passing in 2007. To this day, many locals still share stories of Jimmy at Carpenter Street Saloon, where his name remains engraved in the bar as a tribute to his lasting impact on the community.
Today, Magic continues to race under the stewardship of Jonathan Clarke, owner of the Log Canoe Inn and Higgins Yacht Yard & Marina, and great-grandson of Captain Bob Wilson. More than 130 years after she was built, Magic remains an active competitor and a living symbol of the Chesapeake Bay's rich maritime heritage. Guests staying in the Magic Suite are invited to become part of that story while enjoying waterfront views in the heart of historic St. Michaels.
A Living Chesapeake Bay Tradition
Chesapeake Bay log canoes are historic vessels, but they are not simply museum pieces. The surviving boats are still maintained, rigged, launched, and raced by people who continue to pass sailing knowledge from one generation to the next.
That living tradition is central to the identity of Log Canoe Inn. By naming its six rooms and suites for these boats, the inn gives guests a closer look at a part of St. Michaels history that can still be seen on the water today.
Stay Close to St. Michaels Sailing History
Log Canoe Inn is located at 208 Carpenter Street in St. Michaels, Maryland, near St. Michaels Harbor and the Miles River.
Explore the inn’s six rooms and suites, each named for a historic Chesapeake Bay log canoe, and plan a stay close to the maritime history of Maryland’s Eastern Shore.
