More than the same old playbook

The 35-foot J/105 turned heads in 1991 as the first production boat featuring a retractable bowsprit, and then established class rules to foster affordable one-design racing among predominately amateur crews.

An owner-driver rule, tight restrictions on Group 3 professionals, and annual sail purchase limits has created an inclusive environment to foster participation for over three decades. But that alone is not enough to secure Class health, with this report providing details on one of the thriving J/105 fleets:

While many one-design classes across the country are facing participation challenges, the J/105 Fleet 3 on the Northern Chesapeake continues to flourish, with competitive turnouts, lively events, and an enthusiastic community spirit centered in Annapolis.

Annapolis Yacht Club’s 2025 Wednesday Night Racing showcased the fleet’s depth, fielding 27 boats in Series 1 and 29 in Series 2—the largest class in either series. Beyond weeknight racing, the J/105s have also dominated many weekend regattas, frequently drawing 20 or more boats – figures rivaling those of recent national championships.

Despite the class’s long history—early hulls are now nearly 35 years old and production ended nine years ago—the Annapolis fleet has continued to innovate. The Annapolis J/105 Women’s Regatta, first introduced in 2022, has grown to feature 18 boats, attracting strong local and traveling teams. The regatta has become a must-see event, drawing more spectator boats than many major championships and capping it all with a memorable party.

Building on that momentum, Fleet 3 launched a new event in 2025—the inaugural J/105 Annapolis Invitational Regatta. Inspired by a similar event in Houston and Bermuda, the concept pairs a local Annapolis owner and two crew with a visiting J/105 owner and two traveling crew aboard a local boat. The owner-drivers alternate helming duties each race, producing three scoring divisions: local driver, visiting driver, and combined team.

Led by Fleet Measurer Doug Stryker and hosted in partnership with Eastport Yacht Club (EYC) during the annual Fall Brawl, the event quickly gained traction. Within three days of announcing it, 16 local boats registered to host visiting teams. Within another week, 16 visiting teams from around the country—hailing from Buffalo, Long Island, Chicago, San Francisco, Marblehead, Cleveland, Seattle, and Toronto—had committed to attend.

“Every single Annapolis boat and all 16 traveling teams that committed in the spring showed up to race,” said Stryker. “Most visiting crews stayed with their local hosts, making it easy for everyone to arrive ready to sail and have fun.”

Saturday’s racing faced a light-air challenge, with Race Committee PRO Lee Menard managing one scored race after abandoning the first due to massive shifts. “We restarted and had the visiting skippers take the helms—given the forecast, this could have been their only chance,” Menard explained.

After racing, the fleet gathered at EYC for the annual J/105 Fleet Party, hosted by Velvet Hammer owners Krissy and Brian Robinson and J105 Fleet 3. Kegs of beer, the event’s signature cocktail, the Eastport Lemonade, and a taco bar kept the crowd consisting of Fleet 3 owners and crew and the Invitational competitors, lively well into the night under a tent overlooking Annapolis harbor from EYC back lawn.

A highlight of the evening was the blindfolded spinnaker-hoist competition—a now-legendary tradition that drew cheers from sailors and spectators alike.

Sunday delivered just enough breeze for three races, completing a full four-race series. “We shortened the legs to just over half a mile to maximize racing for both local and visiting helms,” said Menard. “It worked perfectly, even after one general recall.”

Fleet 3 is already planning the 2026 Invitational for October 24–25, targeting 20 local boats and paired teams. “Racers want more than the same old playbook,” said Stryker. “We’re blending competition, community, and creativity to keep the fleet strong and connected. Whether it’s our Women’s Regatta or this Invitational, these events showcase what makes sailing in Annapolis special.”

Photos: https://spinsheet.smugmug.com/SpinSheet/2025-Events-SpinSheet/EYC-Fall-Brawl-2025