Bobby Cragg - 52 consecutive Chester Race Weeks

Aug 8, 2019

52-year Chester Race Week competitor Bobby Cragg (grey cap and jacket at left) helms his Nelson Merek 43 Agincourt in 2017 in the Alpha 1 Fleet (now Distance) on Mahone Bay, Nova Scotia, Canada. (Credit: © 2017 Tim Wilkes / www.timwilkes.com

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 Cragg clarifies that he skippered all 52 consecutive regattas since his first in 1967 aboard the 37-foot Chester C-Class sloop Eclipse (hull #7).

“I had to have my own boat – no one else would have me on theirs,” Cragg laughs.

Summering on and in the sheltered waters of St. Margaret’s Bay’s Schooner Cove on Nova Scotia’s beautiful South Shore, Bobby, as he is still affectionately known, was one of 20 or so neighbourhood water kids who swarmed the bay by rowboat, sail and power.

“When I was 10, my dad, Ed, and a bunch of parents bought 20 second-hand Fleetwind wooden dinghies,” he recalled from his West Chester Village cottage. “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.

Bobby’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. Roué is best known for designing the famous Canadian Grand Banks schooner and long-standing International Fishermen’s Cup champion Bluenose, built in Lunenburg, Nova Scotia, in 1921.

After racing in the AYC Bluenose fleet for a few summers, Ed commissioned a new Bluenose for Bobby – hull #67 – from famous South Shore boatbuilder, Johnny Barkhouse Sr. Around this time, AYC member and sailing Olympian Jack Buckley became Cragg’s sailing mentor.

In addition to being the returning Distance 5 Fleet champion, Cragg reckons he’s won “20 or so” Chester Race Week titles in the 52 he’s skippered so far. Add those to his eight Newport Bermuda Races and 29 Marblehead to Halifax Ocean Races, and it’s no surprise that Cragg is semi-retired from racing. But 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.”

“We make a point of welcoming new skippers and crews to Race Week, especially those who’ve made the effort to get here from far away,” he said. “I believe it’s my job as a veteran competitor and summer resident to be a welcoming host.”

As his father did for him, Bobby 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 Distance Fleet race, “but later, when they’re a little bigger and older”.

The 11 boats that took Cragg through 52 consecutive Chester Race Weeks

1967: Chester C Eclipse
C&C 35 Mk 1 Illusion
C&C 37 True North
C&C 38 True North
Peterson 29 Foxy Lady
C&C 40 True North
Peterson 43 True North
C&C 44 True North
Dobroth 41 True North (Cragg’s all-time favourite)
Nelson Merek 43 Agincourt
2018: Peterson 29 Foxy Lady (Cragg’s 2nd time owning same boat)

Cragg’s 2019 Helly Hansen Chester Race week Crew

Skipper: Bobby Cragg
Main: Sandy Nicholson
Pit: Angus MacLarty
Grinder: Dave Tzagarakis
Mast: Louise Jessome
Bow: Lyle Dobbin, Scott Urquhart
Navigator: Lyle Dobbin
Tactician: none “We know the Bay.”

Hosted by the Chester Yacht Club in the picturesque South-Shore Nova Scotia village of Chester in mid-August each year, Helly Hansen Chester Race Week is Canada’s largest keelboat regatta (four days of sailing) and plays host to more than 120 boats from near and far.

Named one of Sailing World magazine’s 14 greatest sailing events in North America, each August, 1,200-plus sailors arrive on Nova Scotia’s scenic Mahone Bay to compete in one of 15 fleets racing simultaneously on five different race courses. Fleets accommodate everyone from offshore big boats and one-designs, to classic wooden boats, club racers and no-spinnaker cruising boats.

Chester’s sailing regattas were first documented in 1856 and, since then, tourists and locals alike have taken in the natural beauty of the area by both land and sea.

This year’s event takes place August 14-17, 2019

A community-based, volunteer-driven event, Chester Race Week boasts a full schedule of public-friendly events with live music, great food, yacht races, plus racing seminars from internationally renowned sailors, tacticians, boat builders and sailmakers. For schedule, fleets and other info, head to www.ChesterRaceWeek.com

– Michael Dunn