Schooner Libertate with as many sails up as possible in light wind. Photo: Patrick Smith/Pride of Baltimore II

Great Chesapeake Bay Schooner Race: Where’s the Wind?

The majesty of sail was on full display in Baltimore’s Inner Harbor on Oct. 7, when stunning schooners and non-schooners alike showed up to race between 3 and 118 nautical miles down the Bay in the 32nd annual Great Chesapeake Bay Schooner Race. And as endless canvas was raised to send the boats flying down to Norfolk… well … nothing much happened. 

“The race was very, very, very, very, very light air,” says Capt. Jen Kaye of the Schooner Woodwind, a 74-foot working schooner out of Annapolis, MD. “You needed really light-air sails just to move.” 

The wind was uncooperative, flirting first from the northwest and frequently ghosting the fleet entirely. Schooner crews raced to keep forward momentum happening, even if just by inches. 

The Schooner Woodwind with two spinnakers hoisted. Photo courtesy of Jen Kaye.

“We did everything we could just to keep going,” says Kaye, who admits that the Woodwind crew even tried hoisting a spinnaker upside down before resorting to putting two asymmetrical kites up simultaneously. Woodwind was not alone in this decision: Schooner Adventurer, a 56-foot Cherubini, hoisted spinnakers from the fore- and mainmasts as well. This year, Adventurer was captained by Duncan Hood, who took over the helm from Chesapeake Bay legend Art Birney, who passed away earlier in the year. 

The Great Chesapeake Bay Schooner Race hearkens back to the trade rivalry between Baltimore and Norfolk, where merchants needed the fastest schooners to beat their competitors to port. In modern times, however, success in the race has a lot to do with manpower. 

“Other crews are sailing these boats two or three times a year, whereas our crew sails four times a day, often 40-50 hours a week,” says Kaye. “We’re in sync with the boat and with each other.” The Woodwind found the breeze waiting at the mouth of the Potomac before the rest of the fleet, and watched her lead extend on the race tracker. 

The Schooner Woodwind took line honors in this year’s race, her 28th, after 21.5 hours at sea. Adventurer was close behind, as well as the Baltimore clipper Pride of Baltimore II, which lost to the Schooner Virginia, who managed to correct over the Pride by just two minutes. As Pride II later posted on Facebook, “Not too shabby when you consider the two vessels’ designs span roughly a century of maritime history & marine engineering.”

Of the 18-strong fleet to start, only ten crossed the finish line. At Thimble Shoal, the Navy ship USS San Antonio acted as welcoming committee to the first finishers of the 118-nautical mile ace. Crews celebrated their journey with a pig and oyster roast and a sea chantey sing-a-long. 



  1. Virginia, Erik Lohse
  2. Pride of Baltimore II, Jan Miles
  3. Sultana (RET)

1. Woodwind, Jen Kaye

2. Adventurer, Duncan Hood

3. When and If, Jack Maher

4. Mistress, Glenn McCormick (RET)


  1. Sally B, Daniel MacLeod
  2. Tom Bombadil, John Flanigan
  3. Libertate, Peter Carroll  (RET)


  1. Windsong
  2. Norfolk Rebel, Steve Briggs (RET)
  3. Sea Hawk, Steve Nelson (RET)


  1. Bennu, Julianne Fettus
  2. Howard Blackburn, Mark Rosener (RET)


  1. Jolly Dolphin, Jack Zuraw

Duffy Perkins