2024 The Pilot Regatta
Welcome to the 2024 The Pilot Regatta Information page.

2024 Pilot Regatta Description

Who: All are invited

What: The Pilot Regatta with classes for Racing, Cruising, and One Design.

     *The summer Laser regatta is being held as a separate event

Where: PYC

When: July 13 and 14

Why: Because sailboat racing is fun. Do you need another reason?


We’ve moved the Pilot Regatta to July 13 and 14 in search of better weather probabilities and greater event participation. We’re reaching back and remembering Those days when this regatta was a 2 - day event. We think it would be more fun to spend 2 days racing with you on the water rather than just the one.

We’re planning for the first day to be a longer course race with views of the islands of Casco Bay, a light house or 2, and if I have my way, Fort Gorges. (July 14th is Bastille Day and Fort Gorges is the closest thing to the Bastille we have to sail around). This race will finish near Clapboard Island to bring you all into close proximity of PYC for a fun evening of good music, good food, and some good socializing with friends you know and friends you will know.

Day 2 will be a day of shorter course races. It would be really fun to get 3 races on Sunday. If we can, we will. We’ll plan to start the last race of the day with careful consideration for getting everyone to the lawn at PYC for a short awards ceremony and one more chance to visit with your sailing friends off the water.

This will be the final race of the “Casco Bay Challenge''. The Casco Bay Challenge is an award open to all members of Centerboard, Portland and Harraseeket Yacht Clubs. The Challenge is to race in all 3 regattas (Centerboard Regatta on June 8, The Harraseeket Regatta on June 22, and The Pilot Regatta on July 13 and 14). That yacht that competes in all 3 events and has the best overall score is the winner of the Casco Bay Challenge. The winner receives free admission to all 3 races in the following year, a gorgeous hand-crafted rigging knife, and the boat's name on the perpetual trophy.

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