From June through September, the Chesapeake Bay’s fleet of log canoes stages a weekly water ballet, as a delicate flotilla of century-old sailboats competes for bragging rights.
These regattas unfold up and down Maryland’s Eastern Shore, with races held on the Miles, Tred Avon, Chester, and Choptank rivers.

A Race Unlike Any Other
Log canoe races are defined by long runs along the river and dramatic, often hair-raising mark roundings. It is not uncommon for several boats to unceremoniously dump their crews into the water, where they await rescue by tenders that follow the racecourse.
“Once she goes over,” cautions Island Blossom’s long-time skipper Corbin Penwell, “it’s all over for the racing. Pretty tough to get these boats back up and sailing. We save the beer for the ride home and live to race another day.”
What is a log canoe?
Today, fewer than 24 log canoes remain actively racing on the Chesapeake Bay and surrounding rivers. Originally built as simple workboats, these vessels were constructed from three or five logs fitted together to form a hull.
Modern racing canoes range from 23 to 34 feet in length and carry between 500 and more than 1,200 square feet of sail.
Crews act as moveable ballast, scrambling along hiking boards to keep the boats upright. When the wind shifts unexpectedly, the boats can tip into a slow-motion roll that is nearly impossible to stop.
How to Watch the Races
Viewing log canoe races can be limited, but the experience is well worth the effort.
For races on the Miles River, the Chesapeake Bay Maritime Museum offers options for viewing from land or water. Departing from the museum campus, Patriot Cruises offers a narrated cruise aboard a 1920s replica steamship. If you prefer a more intimate setting, the museum offers two-hour charters for up to six people on select racing weekends. St. Michaels Sailing Charters offers historic sailing yacht tours or luxury catamaran sails.
Additional viewing opportunities may be available through sponsoring yacht clubs or on-shore depending on race locations.
Stay the Weekend
If you’re coming in for the races, a variety of hotels, bed and breakfasts, and vacation rental properties are available throughout Talbot County to meet the needs of your travel party. For an immersive experience, choose the Log Canoe Inn. Named after the historic Chesapeake Bay sailing log canoes, the historic inn has been renovated and decorated to honor the sailing tradition.
Written by Craig Ligibel, an award-winning Annapolis-based photojournalist who has spent more than a decade documenting sailing on the Chesapeake Bay.
Photo courtesy of the Chesapeake Bay Maritime Museum, photographed by Sharon Thorpe.
For more information, the Log Canoe Sailors Facebook page is a valuable resource.


