As a Marblehead local, Gary Gregory has participated in an impressive twelve Marblehead to Halifax Races aboard his historic Twelve Metre, Valiant. Those who have been in Marblehead harbor have surely marveled at the boat. Built according to the International Third Rule America’s Cup in May of 1970 under the design of Olin J. Stephens at Robert E. Derecktor Yacht Yard, she is one of the heaviest Twelves ever built. Valiant calls New York, NY, her original homeport but has since spent time in Providence, RI, St. Petersburg, FL, and Long Beach, CA, before being brought to Marblehead in 1989 by Gary Gregory. She has undergone several advanced modifications under the ownership of Gregory to improve her speed and symmetry. 

Gregory and his crew began their involvement in the Marblehead to Halifax Race in 1991, missing only two races; the first in 2001 when they participated in the America’s Cup Jubilee in Cowes, England, and the second in 2007 when they participated in the Twelve Metre World Championship in Valencia, Spain. Gregory thinks back on his favorite memory of the MHOR in 2005 when he won his class and finished second overall. His two sons, Oliver and Eliot sailed aboard Valiant as well as Cutter Herlihy’s son, Will. The three boys ranging in age from nine to fourteen. Gregory remembers this race as being particularly special because of the strong family connections aboard having two generations of Gregory’s and three generations of family members of long time crew member, Ralph Carlton, sailing that year. Gregory recalls, “We sent the kids up to collect our trophy and at first no one believed they had competed in the race. The return delivery was delightful with multiple sightings of whales, dolphins, and other interesting sea life.” 

Valiant fields an impressively loyal crew, with many of them sailing together and enjoying each other’s company since the 1980s. These crewmembers all have a tremendous amount of blue water sailing experience in a vast range of boats, helping to lead to the team’s success throughout the years. Gregory impressively notes that “Some sailors who started sailing with us as children now have children of their own. This year we’ll range in age from early 20s to mid 80s.”

This year’s MHOR will prove to be exciting for Gregory and the crew of Valiant to participate in. Despite the fact that they know the boat and the race well, Gregory says that there is still much to learn and that at the end of each race, they reflect upon the things that went well and what did not go as planned in order to improve for future races. A few years ago, they switched to asymmetrical spinnakers because they are easier on the crew than their symmetrical counterpart. In anticipation of this year’s race, Gregory says, “We’re finally getting the hang of them and are looking forward to seeing if we can be more competitive reaching this year under a full moon.”

This year’s race boasts an impressive fleet including Valiant. Sailors and spectators alike all have high hopes for ideal sailing conditions and look forward to cheering on all competitors!