With a good clip of wind behind all three entrants, the Annual
‘Port & Starboard Yacht Club Regatta was held on August 11th, 2007.  Sailing out of Bucks Harbor, Machias Bay, the smallest yacht
of the bunch named Who and owned by Stephen and Starr Woolsey of Machiasport was the winner.

With a crew of two, Steve Woolsey and his crewman, Jim Sherman
of Machiasport, finished the approximate 10 mile course in an impressive 2 hours and 47 minutes (corrected by a one hour 35 minute handicap) in their 18 foot Cape Cod Catboat Who .  A extremely well executed navigation strategy that minimized come abouts and tacks to reach each of two of the race markers and cross the finish line made the difference for the crew of the Who .  The boat was built in 1972 by Nowak & Williams.

In second place was Lola, a Passport 40 Sloop built in Taiwan in 1985 and owned by John and Judy Bielecki of Machiasport and Belgrade, Maine. Captain John Bielecki was supported by crew Harper Dean of East Machias and Joe Transue of Bucks Harbor and Newport, Rhode Island.  Lola crossed the finish line in 2 hours and 27 minutes with no handicap as it was the largest boat in the race.

Crossing the finish line in third place on corrected time was Alan Lewis of Jonesport sailing Sparrow.   Sparrow is an Island Packet 27 Cutter built in 1988 by Island Packet Yachts at an overall length of 30 foot long. Alan’s crew was Michael Leonard of Machias. Sparrow crossed the finish line in 3 hours and 9 minutes (with a 35 minute handicap).

Dana Urquhart of Jonesboro served as Race Commodore and ran
the Committee Boat, with Chris Urquhart of Bangor assisting with Flags and Virginia Transue of Bucks Harbor aboard. Timekeeper and on the Race Committee was Bill Transue Jr. of Bucks Harbor.

(text taken from a previous site: http://medowinweb.com/Port/Regatta2007Text.html )