History of the Log Canoe Inn

Comprising of two homes joined together, built in 1790 and 1810, the inn has served many purposes. Primarily, the inn was used as a private residence for the first almost 100 years of existence. Then, from 1921 until 1930, the main house was the first original clubhouse of the Miles River Yacht Club - know as the home of the Chesapeake Bay Log Canoes.

In the 1970's, the house was converted into one of the first boarding houses in St. Michaels, with five small bedrooms and only one shared bathroom. The sail shed was originally used as just that - a sail shed - storing boat sails and spars, until being renovated in the early 2000's into two guest suites with en suite baths.

Over the years, many renovations and care has given the property new life and added luxury amenities, but we still strive to keep the history that the home held hundreds of years ago.

In 2021, Jonathan Clarke purchased the Log Canoe Inn. Jon is also the owner of Higgins Yacht Yard, the oldest and only still working boat yard in St. Michaels, dating back to 1770 as the original port and shipyard of the town. The Log Canoe Inn and Higgins Yacht Yard are located just adjacent to one another, on opposites sides of Carpenter Street. Jon was born and raised here on the Eastern Shore of Maryland, and can trace back his family lineage in Talbot County for hundreds of years. Jon is also the proud owner of the log canoe "Magic", which was built in 1894, and has been owned by his family since 1923. Jon's great great grandfather was Captain William "Bill" Green, who was the owner of the log canoe "Mary Rider", and also one of the original founding members of the Miles River Yacht Club.

In honor, two of our rooms are now named after the "Magic" and "Mary Rider".

History of the Chesapeake Bay sailing log canoes

Originally simple workboats, log canoes are constructed of either three or five logs fitted together to form the keel and sole of the boat. The 19th century skippers would race their boats back to shore, loaded with oysters, to reach the dock first and receive the highest price for their catch of the day. This started the idea of making the boats faster with larger sails. Most of today’s log canoes are 75 to 100 years old, with less than 24 left remaining. Log canoes are distinctive with narrow beams and over canvased schooner rigs that make the boats extremely tender, with a significant propensity for capsizing. Counterbalancing the huge sail area are sailors balancing out on boards, commonly referred to as moveable ballast. These sailors perch at the end of 15-foot-long spring boards that they move from side to side as the boat changes tacks. Watching these big men traverse the boards is a study in fluid dynamics. While not quite ballerina-like in their movements, there is a certain synchrony as they slide down the boards, move them to the other side of the boat and clamber up the opposite side all the while timing their descent and ascent to the flow of the sails as they come across the rig in a slow-motion tack.

There is an old sailing adage: “If two boats are sailing the same course, there is a race going on whether the other captain knows it or not.”

MARY RIDER - 1877

"Mary Rider" measures about 28 feet in length, and was built in Tilghman Island in 1877 by James Lowry. She first served as a workboat, as many log canoes did before her. Before acquiring her present name, she was known as the "Louise," named after Louise Kemp of Wades Point, Maryland. By 1917, she had been abandoned and was left on Fogg Beach in St. Michaels, until Captain William "Bill" Green found her, and gave her a new life. She was renamed "Mary Rider" after Bill's youngest daughter, and after a complete reconditioning, she was out with the fleet again, participating in races. She won the Governor's Cup, a perpetual trophy sponsored by the late Maryland Governor Ritchie, three consecutive years in a row in 1928, 1929, and 1930. Bill had five daughters that would make up his crew, along with himself. One of his daughters, Tunis Green, eventually was married Captain George "Bob" Wilson, who purchased the log canoe "Magic" in 1923. Obviously a very close familial connection, the Wilsons and Greens raced competitively against one another on the Mary Rider and Magic for many years. Unfortunately, the Mary Rider's last documented race was in 1948, and she is reported to have been left ashore on Foggs Beach, the same beach she was originally found, and deteriorated at the mercy of the elements.

MAGIC - 1894

"Magic" was built in 1894, by Charles Tarr in St Mary’s Square in St. Michaels, Maryland, She measures 34'-3 5/8" long with a beam of 6'-11". She served as a commercial oystering vessel until 1923, when Captain George "Bob" Wilson paid $100 for her, and he and his good friend and sailing icon, Lowndes Johnson, rigged her up for racing. After her conversion, Magic proved to be one of the fastest canoes in the fleet, winning the first Governor's Cup race in 1927. Bob's son, George Wilson Jr., raced her from in the 1960's and 1970's, until his younger brother, James "Jimmy" Wilson took over the helm, until his passing in 2007. You may hear a few Jimmy Wilson stories from the locals around the local watering hole, Carpenter Street Saloon, where Jimmy's name is engraved into the bar. Magic's current skipper is Jonathan Clarke, owner of Higgins Yacht Yard and the Log Canoe Inn, and great grandson of Captain Bob Wilson.

ISLAND LARK - 1892

Skipper Tad DuPont was quoted in 2011 saying, “In log canoes, it's a total team effort. Some of us on Lark’s crew have been together for more than 30 years. Lark’s crew is an example of how people from all walks of life have gotten together and this is their common bond.” DuPont says that on recent races Lark’s crew has been comprised of every age group from sailors in their teens, to some almost 70 years old. He also says that the competition sailing on log canoes is stronger than any other racing circuits he's competed in. As an example, he says that the Island Lark was built on Kent Island in 1901 with the expressed purpose of beating the Island Blossom, a log canoe built in 1892 by Sydney Covington. “I find it ironic that a hundred years later, those two boats are still locked up,” duPont says. The Blossom and the Lark are frequent one-two finishers. Tad has passed on the heritage to the next generation to his daughter and son-in-law, Corey and Andrew Devlin. You will see the Lark launching from Higgins Yacht Yard during most regattas in the Miles River.