History & Tradition
The Monhegan Island Race, a nod to tradition with a spark of adventure….
PYC’s flagship offshore event was first held in 1928 with the Manana Island race for smaller boats beginning in 1957. By the late 1960s, in conjunction with an overall growth in U.S. sailing, the number of entries began to swell, peaking with 142 boats in 1985. Famous race boats and sailors participated from throughout the U.S. including La Forza del Destino, Stampede, Freebooter, Toscana, Déjà vu, Gem, Pioneer, and Starlight Express. Boats from the Maine Maritime Academy, US Coast Guard Academy, US Naval Academy and the US Merchant Marine Academy regularly attend. Portland Yacht Club has always been well represented by Merle Hallett with a sequence of boats named Scaramouche, Jim Stanley with his Capellas, Bill Reynolds with Matriarch, Dick Hale in Bandito, Ned Semonite and family in Black Owl, Bob Kellogg and Geoff Emanuel in a variety of boats and recently, Scott Smithwick in Kaos.
Monhegan Island Race
PYC member Merle Hallett competed in nearly every race from 1960 to 2010 having won his class numerous times. As owner of Handy Boat for many years, he oversaw the construction of one of the many Scaramouches. Shown here is a custom 42’ Taunton designed racer built in 1977.
In 1991 the wind blew 35 to 60 knots in an unforecast and short-lived mini gale that occurred during the first six hours of the race. All but 9 boats retired, 5 of those still racing were boats in the Monhegan Island course. Bully, a Baltic 50 won the Monhegan that year.
Windy conditions for the 1992 race allowed Encore, James Dolan’s Santa Cruz 73 to set the course record of 10 hours 46 minutes and 57 seconds.
Portland Yacht Club member Scott Smithwick has put together one of the best race records in history. Between 2000 and 2019 Smithwick has won his Class more than 10 times with 4 different boats. His Frers 41 Kaos has been awarded the most hardware, in Monhegan Race history.
Manana Race
The Manana Race, a roughly 90nm race, was developed in 1957 for a new class of boats. Smaller pleasure boats were becoming more mainstream and the addition of “plastic fantastic” fiberglass boats in the late 70s really gave rise to large fleets of 30’ boats that wanted to race offshore.
The run of Manana Race wins by PYC member Dr. Del Damboise, sailing his Pearson 30 Barbara, has few equals in the annals of the race. Notably he won the race 5 times including in a row from 1981 to 1984.
Jan Pedersen in the Morgan 27 and J-30 Heitorik and Wayne Smith in Defiant both have 3 Manana wins apiece, but recently David Ruff and family have amassed at least 6 wins, in Go Dog Go in the last 10 years.
Orrs-Bailey Yacht Club member Abbot Fletcher finished second in class in his beloved Tripp 37 Majek in 1999, his 34th Monhegan Race. Sadly, he passed away four months later. The Manana Island Race trophy was renamed in his honor soon afterwards. Abbot won his class in 12 Monhegan and Manana Races over the decades between 1962 and 1999. This trophy was re-dedicated to the racing class in the Seguin Island Sprint.