Maggie Flanigan Perpetual Sailing Trophy Dedicated

Annapolis J/105 Women's Sailing Regatta Remembers Popular Sailor

Remembering the spirit of J/105 racer Maggie Flanigan, the J/105 Women’s Regatta will be awarding the Maggie Flanigan Perpetual Trophy to the “Best Dressed Crew” of the regatta on Sunday, September 1.


Maggie Flanigan, center, with the rest of the “Best Dressed Crew” on Firebrand at the 2023 J/105 Women’s Regatta Awards Ceremony. Photo by Will Keyworth/ SpinSheet

Flanigan was a member of 2023 winner of the Best Dressed Crew, a trophy that did not exist until they arrived on the racecourse, to the delight of the race committee, in their bright pink and white attire. A self-proclaimed “Seamstress, Fiber Artist, Costumer, Sailor” the trophy remembers the joy, light, and humor which she brought to her serious pursuits.

Flanigan was a smiling presence, a leader, and a skilled singer-seamstress-sailor who bridged social gaps, connecting people of different skill levels and ages. She exemplified many of the characteristics the Women’s Regatta aims to promote, including excellent competition and camaraderie. The Women’s Regatta dedicates this perpetual trophy in the hope that this memory of Flanigan will inspire all to be better sailors, better people, and to enjoy life.

About the sailing event

The J/105 Women’s Regatta is a one-day, one-design regatta, hosted by J/105 Fleet 3, with the Sailing Club of the Chesapeake (SCC) as the Organizing Authority. This year’s regatta, with 18 boats registered to date, will be the largest edition. Festivities will begin with a Friday night practice, on August 30, a skipper’s meeting on Saturday evening, August 31, and an awards party following the racing on Sunday, September 1.

J/105 Fleet 3 the largest fleet in the J/105 class, and one of the biggest amateur one-design fleets in Annapolis. This women’s regatta is part of an overall J/105 class initiative to get more women involved.

Multiple J/105 women’s events have been held in 2024, including in Toronto, San Francisco, Seattle, Galveston Bay, and Charleston.

The Sailing Club of the Chesapeake (SCC) altered the J/105 rules for this regatta to encourage all women teams. The SCC specializes in hosting “signature” regattas that each have their own personality, like the EWE Spirit Regatta, the J/105 Women’s Regatta, and the Hospice Cup, to be held on September 14.

Links for more:

Obituary and Official Regatta Page and photos from 2023 event.