Annapolis Yacht Club has rededicated one of its most prestigious perpetual trophies in memory of Allsopp, who had a passion for offshore sailing and put a ton of blue water miles under his belt. The James Allsopp Seafarer Trophy will next be presented during the Annapolis to Newport Race prize-giving ceremony, in June of 2025, if a qualified entry meets the criteria.

The trophy will be presented to the skipper of the boat with the best combined performance in the upcoming Annapolis-to-Newport Race and the previous Newport-to-Bermuda Race, which was held in June of this year.

Established in 2013 and initially named the Chelsea Clock Trophy, it was renamed in memory of Allsopp prior to the 2017 edition of the Annapolis-to-Newport Race. Allsopp was a stalwart member of the Annapolis Yacht Club from 1977 until his death in June, 2016 at the age of 72 after a nearly four-year battle with brain cancer. His widow, Holley, and two sons, James and Cole, were pleased to learn their husband and father’s legacy would be perpetuated through the James Allsopp Seafarers Trophy. The original trophy was destroyed in the Annapolis Yacht Club’s devastating fire in 2015. In 2017 a generous donor, who wishes to remain anonymous, replaced the trophy with the caveat that it be renamed in memory of Allsopp.

“Our family is very grateful that Annapolis Yacht Club has recognized Jim by naming a perpetual trophy in his memory,” Holley Allsopp said. “It means a lot to us as a family to know that Jim is remembered. Jim loved Annapolis and Newport, having owned homes in both locations, so it is very fitting for the award bearing his name to be part of the race that connects those two great maritime towns.”

Jim Allsopp competed in the Annapolis-Newport and Newport-Bermuda races with many prominent owners in addition to Collins, including Al Van Metre on his renowned race boat Running Tide.

“Jim was the type of guy you were immediately comfortable with on a boat because he was so professional and so engaging. He had a remarkable way of getting everyone to do their jobs and do them well,” Holley said.

Allsopp grew up on Long Island and spent considerable time on the water racing a variety of dinghy designs. He sailed collegiately at the University of Miami and initially gained prominence in racing circles by capturing the 1976 Star World Championship in Nassau, Bahamas — beating such class legends as Tom Blackaller, Pelle Petterson, Malin Burnham and Bill Buchan.

He followed that career-making victory by winning the Star European Championship, held the same year off Marstrand, Sweden. That was enough to convince Lowell North that he’d discovered an up-and-coming talent, so he asked Allsopp to serve as trimmer aboard his 12-meter Enterprise for the 1977 America’s Cup Defender Series.

Allsopp was one of the original “tigers” personally hired by Lowell North to operate North Sails lofts around the country. Allsopp took over the sailmaking loft that was located on Kent Island and opened a sales office in Annapolis. He owned the local loft from 1979 to 1985 when Terry Kohler bought North Sails and ended the franchise arrangement.

Graduating college with degrees in chemistry and electrical engineering, initially came to the area to work for Westinghouse. He gave up a fledgling career as an oceanographer and got into the sailmaking business with the old Murphy & Nye loft in Annapolis.

He hired Jonathan Bartlett in 1984 and the Past Commodore of Annapolis Yacht Club is still with North Sails Chesapeake 40 years later. Bartlett credits Allsopp with teaching him the ropes of being a professional sailmaker and how to work with customers.

“It is very appropriate for the Annapolis Yacht Club to name this trophy in memory of Jim, who was such a huge name in the sport of sailing at an international level,” Bartlett said. “Jim was always incredibly supportive of the Annapolis-to-Newport Race and was a regular participant.”
While Allsopp developed as a dinghy sailor and later excelled in the Star, a 23-foot one-design keelboat, he came to love ocean racing aboard larger sailboats. He relished the role of program manager for offshore passage.

“Jim loved building a team and developing the chemistry and camaraderie that is critical to success in offshore racing,” Bartlett said.

Due to his status as one of the top pros in the North stable, Allsopp became a worldwide ambassador for the company and helped introduce Italy and Spain to the international racing scene by overseeing their Sardinia Cup and Admiral Cup teams. He served as regular helmsman or tactician for King Juan Carlos of Spain when the latter skippered the Spanish Maxi, One-Ton or Copa del Rey teams.

Allsopp passed his passion for sailing on to his two sons, both of whom became talented competitors in their own right. James Allsopp was a member of the intercollegiate dinghy team at the Naval Academy, while Cole Allsopp sailed for the College of Charleston.

One of Jim Allsopp’s greatest joys was having both boys aboard Chessie Racing for an Annapolis-to- Newport Race. James and Cole were able to see first-hand why their father loved blue water racing and was such an outstanding crew boss.

“My father just loved being out with a group of friends and getting them to work together to maximize performance,” James said. “Winning was important, but not more so than the experience. He understood the importance of having the right type of people aboard the boat. He didn’t like anyone being negative or having a bad attitude. He wanted the experience to be fun for everyone.”
Cole Allsopp was 12 years old when he and James accompanied their father on a transatlantic crossing to Ireland. He completed an Annapolis-to-Bermuda Race with his father as a teenager and has fond memories of racing the family Farr 30 in Annapolis Yacht Club’s Wednesday Night Series and other local regattas.

“I’m learning all the time about what a major impact my father made on the local sailing community,” Cole said. “This trophy being named in his memory is further proof that he left a lasting legacy.”

James Allsopp has followed closely in his father’s footsteps as a professional boat captain running grand prix racing programs out of Annapolis. He was thrilled to learn about the James Allsopp Seafarer’s Trophy and noted it is the second time that has happened, as the winner of the International One-Design Celebrity Invitational Regatta held in Nantucket now receives the Jim Allsopp Trophy.

“I’m really happy that my father is being remembered in this way. It’s a cool thing to have perpetual trophies that recognize and honor past sailing greats who made such an impact and he certainly fits that description,” James said.

The James Allsopp Seafarers Trophy is one of many perpetual trophies awarded during the Annapolis-to-Newport prizegiving ceremony. To learn more about the others, visit: https://www.annapolisnewportrace.com/trophies