Reflections on the Great Chesapeake Bay Schooner Race 2023

Light winds and currents challenged schooner crews in the 2023 edition of this classic Bay race.

Each year, in October, the Great Chesapeake Bay Schooner Race (GCBSR) departs its start line off of Annapolis, MD. The schooners drive southward, all the way to the end of the bay to Norfolk, VA, where, tired, but proud, they tie up for a weekend of festivities which include educational tours, shanty singing, an oyster roast and general, rambunctious camaraderie. Each year brings different challenges for these old-school, but elegant ladies.

Schooner Adventurer Crew Cheer
The author and his crew aboard Adventurer. The winds are generally out of the south for the start of the GCBSR, and this year was no exception.

The winds are generally out of the south for the start of the race, and this year the start of the race was no exception. The crazy thing was that this wind was dying over a slack tide. It was as if nature was trying to run the clock down on our timeline and keep us from the frivolity at the end of the race. The breeze continued to die away as Class A and AA boats crossed the line. The Class B and C boats were 10 minutes behind the big kids and lumbered forward in about two knots of wind. Sails went up and down; fishermen, gollywobblers, spinnakers; all were tried to little advantage.

Schooner Sultana
The Schooner Sultana in Baltimore Harbor. Photo courtesy of Duncan Hood

The winds continued to be light to non-existent over the next 60 miles down to Cove Point where throughout the night, the boats tacked listlessly and aimlessly across the shipping lanes, dodging tugs and ships as best they could with little or no steerage. It was a night of frustratingly slow maneuvering with currents both fair and foul playing with the schooners like a cat might play with a catnip toy. The real challenge was just staying alert.

In the early house of morning, a light westerly breeze sprang up and saved us all from death by boredom, and we skipped along the western shore at six-plus knots for about three hours until sunrise when, again, the winds dropped out. By 10 a.m. we were once again drifting aimlessly, with our class A boat staring at Smith Point, the southern entrance to the Potomac River.

In the morning, we received a general text message telling us that the racecourse was shortened to Smith Point for Classes AA and A. There we sat, two miles from the finish, so tantalizingly close, twiddling our thumbs for the next few hours when, finally, the race was terminated at 12 o’clock, noon. All vessels then gratefully fired up their engines and motored the final miles, full of disappointed, yet relieved and happy crews anticipating showers, shaves, and a well-earned shore leave.

students aboard schooner
Student education is an important part of the Great Chesapeake Bay Schooner Race weekend. Photo courtesy of Duncan Hood

All arrived in the early hours of Saturday and caught what sleep we could before the Awards Party and Oyster Roast began. Saturday also brings educational tours for kids, deck tours for the public, and crews just carousing among the boats. The energy amped up and the fun began. Proceeds from the race entry fees were donated to local charities, and shanty singing ran well into the night; a fitting end to this unique and quirky race, and a well-deserved celebration of classic boats of the past and the crews that sailed them. Would they do it again? In a heartbeat. They'll be back next fall. Let’s all pray for more wind!

By Duncan Hood, Schooner Adventurer

Learn more and find the recipeints of the 2023 Special Awards as well as racing and fundraising results at