While many one-design classes across the country are facing participation challenges, the J/105 Fleet 3 on the Chesapeake continues to thrive, with competitive turnouts, lively events, and an enthusiastic community spirit centered in Annapolis.
Competition, Community, and Creativity in the J/105 Class
In addition to showcasing its deep fleet with 29 boats on the start line at Annapolis Yacht Club’s Wednesday Night Series last summer, Fleet 3 draws 20 or more competing boats to weekend regattas from the Helly Hansen Sailing World Series in springtime to the J/105 Chesapeake Championships in the fall; these figures rival those of recent national championships for these 35-year-old boats. The Annapolis J/105 Women’s Regatta, first introduced in 2022, has grown to feature 18 boats, attracting strong local and traveling teams.
Building on that momentum, Fleet 3 launched a new event in 2025: the inaugural J/105 Annapolis Invitational Regatta, held concurrently with the Eastport Yacht Club (EYC) Fall Brawl one-design regatta October 25-26. Inspired by similar events in Galveston Bay and in 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 EYC, 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 and Long Island, NY, Chicago, IL, San Francisco, CA, Marblehead, MA, Cleveland, OH, Seattle, WA, and Toronto, Canada—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 Maynard 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,” Maynard 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 J/105 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, crew, and the invitational competitors lively well into the night under a tent overlooking Annapolis Harbor from EYC’s 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. If you haven’t experienced this competition, your only chance is to race on a J/105 next season to ensure you are invited to the party.
Sunday delivered just enough breeze for three races, completing a full four-race series. “We started at 10 a.m. and shortened the legs to just over half a mile to maximize racing for both local and visiting helms,” said Maynard. “It worked perfectly, even after one general recall.”
Trophies were awarded by 4:30 p.m., allowing visiting teams to travel home Sunday night or go out on the town, if leaving on Monday. The local driver scoreboard saw Patriot (also known as PAT RIOT) take top honors, followed by Mirage in second, and Velvet Hammer in third. The top five teams were separated by only three points.
Among the visiting teams, Richard Stearns’s Chicago-based Five claimed the win, with Jack Denker’s team on Idaho from Boston in second, and Mark Fruin’s Nyctosaur from Chicago in third, after the tie breaker.
In the combined team results, Patriot/Nyctosaur earned the overall championship. Mirage/Mandate took second, and Velvet Hammer/LouLou finished third.
Fleet 3 is already planning the 2026 J/105 Invitational for October 24–25, targeting 20 local boats and paired teams, and there is also discussion with other local one design fleets to join in on the concept and event.
“Racers want more than the same old regatta rise and repeat playbook,” said Stryker. “We’re blending competition, community, and creativity to keep the fleet and class strong and connected. Whether it’s our J/105 Women’s Regatta, the Annapolis YC 3-2-1 which includes J/105 match racing, or this J/105 Annapolis Invitational Regatta, these events showcase and celebrate what makes sailing J/105s in Annapolis special.”
As participant Brian Denker of Team Idaho summed up: “It was kind of a who’s who of J/105 sailors from all over, a mini-nationals. We learned so much from our hosts and saw just how talented this class is."
Find full regatta results at yachtscoring.com.
