Remembering Richard Sides: a life under sail and the spirit of the 'Round-the-Island Race
by Barby MacGowan 3 Apr 20:40 BST
July 25-26, 2026
He sailed 13 ‘RTIs, many with his son © Barby MacGowan
As preparations begin for the 89th edition of Edgartown Yacht Club's 'Round-the-Island Race ('RTI), the Club pauses to remember Richard Sides, whose lifelong devotion to sailing - and 13 years competing in this event, many times with his son Rob - embodies the very spirit of the race.
Sides began sailing in 1954 with the Dublin University Sailing Club and went on to race competitively in Ireland and England. While earning his MBA at MIT, he worked with Ted Hood on early computer applications for sail design, leading to a career with Hood Sailmakers and Hood Yacht Systems from 1972 to 1981 and a move to Marblehead, Mass.
After joining Eastern Yacht Club in 1977, Sides became an active racer and Race Committee volunteer. He competed in two Marblehead-to-Halifax races and, after purchasing the Sabre 28 ketch Atalanta in 2004, undertook a 34-day cruise with his son through the Bay of Fundy and the Saint John River. Though not built for speed, Atalanta proved formidable under his skilled handling, earning victories in Hull Yacht Club's Great Chase (2012) and Edgartown Yacht Club's 'RTI (double-handed, 2016) and Round-the-Buoys Race (double-handed, 2017).
"My father always sailed the 'RTI doublehanded," said Rob Sides. "Atalanta was very stable, so we never needed 'rail meat.' He loved being fully engaged, handling multiple responsibilities rather than coordinating a large crew. He preferred sailing with a small, capable team who knew the boat."
In 2022, Sides received the 'RTI's inaugural Incognito Trophy, awarded to the team that best exemplifies passion, perseverance, and commitment to the sport during Edgartown Race Weekend. His son Rob stood beside him as his father's teammate.
Reflecting on their years together, Rob added: "It's no exaggeration to say the 'RTI was the first event on my dad's calendar every year. He loved everything about it: the two-day sail from Marblehead, the strategy of tides and currents, and the challenge of a race that was never the same twice. He loved Edgartown - the harbor, the library, the osprey nests - and the rhythm of mornings aboard...making coffee at dawn...it was all part of the experience."
From Dublin Bay to Vineyard Sound, Richard Sides' story reflects the enduring appeal of the 'RTI, a race that connects generations, rewards preparation, and celebrates both the art and science of sailing. Sides will be forever remembered for his quiet determination, sportsmanship, and deep love of the sea.
Today, Atalanta rests ashore in Marblehead and will be sold this year, marking the end of a remarkable chapter for the Sides family.
More about the 'RTI
Edgartown Yacht Club's 'Round-the-Island Race returns to its traditional July time slot in 2026, with the 89th running scheduled for Saturday, July 25. The shift from June has been welcomed by competitors seeking more consistent breeze and midseason readiness.
One of yacht racing's longest-running distance events, the 'RTI features divisions for PHRF Spinnaker, PHRF Non-Spinnaker, PHRF Doublehanded, and Multihull, drawing a diverse fleet from classic wooden yachts to high-performance offshore programs.
The Venona Trophy, awarded since the race's founding in 1938, remains its most coveted prize.
Service Academy sailing teams receive free entry, and complimentary moorings are available to the first 50 paid entries. Social highlights include a Welcome Party on Friday, July 24, and Awards on Sunday, July 26.
Registration fees are $500 through June 12, $600 through July 3, and $700 through July 17, with a full refund available through July 17.
For more information, including the Notice of Race, visit www.RTIrace.org or contact Margaret Passafiume at or (508) 627-4364 x18.