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For the fun, chaos, and friendships

Published on August 7th, 2019

Getting his Peterson 29 Foxy Lady ready for what will be his 53rd consecutive Chester Race Week – likely the regatta’s longest unbroken competitive run – 73-year-old Halifax criminal defense attorney Robert ‘Bobby’ Cragg clarifies that he skippered all 52 consecutive regattas since his first in 1967.

“I had to have my own boat – no one else would have me on theirs,” the charismatic serial competitor grinned.

Held in the picturesque South-Shore Nova Scotia village of Chester, the 2019 Chester Race Week on August 14-17 has 120 entrants from near and far. Cragg is among the largest fleet in the Distance Race division.

It all began for him while summering on and in the sheltered waters of St. Margaret’s Bay’s Schooner Cove on Nova Scotia’s beautiful South Shore, with Cragg as one of 20 or so neighborhood “water kids” who swarmed the bay by rowboat, sail, and power.

“When I was 10, my dad and a bunch of parents bought 20 second-hand Fleetwind wooden dinghies,” he recalled. “Our parents said ‘here you go’ and we figured out how to sail by trial and error and, naturally, we began racing each other off the community wharf.”

Those Fleetwinds were the start of what later became the current St. Margaret’s Bay Sailing Club.

Cragg’s dad bought him his first keelboat, a second-hand, 23-foot Bluenose – Vagabond (hull #1) – when he was 14. The Bluenose is a one-design racer designed by William James Roué and originally commissioned by the Armdale Yacht Club (AYC) in 1946 and remains a competitive regional class today.

“We got into sailing and remain in it for the fun, for the chaos of the starts, and for the friendships that have grown to include so many people far and wide,” he said. “The feeling that began for me as a boy in Schooner Cove has moved to Chester Race Week as it has for so many of the region’s sailors – Race Week is a rallying point for a larger, fun, summer community experience.”

While he is now semi-retired from racing, he reserves space in his calendar for Chester Race Week’s big-boat distance fleet in mid-August each year.

“I don’t have to send emails to any of my friends, it’s understood that we will be doing Chester Race Week – it’s part of the rhythm of our year as it is for so many families and crews who come annually.”

As his father did for him, Cragg recently bought a new Bluenose, Ghost, (hull # 182) for his daughter, Christine, and her family. With two granddaughters in junior sailing at the Chester Yacht Club, Cragg looks forward to the day when he can welcome the girls aboard Foxy Lady for their first Chester Race Week.

Event details:

Source: Michael Dunn

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