Masks and Mainsails R19 Charity Regatta

Join us for a day of competitive racing on Boston Harbor

Join us on Saturday, Oct 3 for our first (and hopefully last!) ever Masks and Mainsails regatta. Our Rhodes 19 fleet has been outfitted with beautiful new sails (with loose-footed mains, for the first time!) just begging for a big regatta. We'll celebrate the 2020 sailing season that almost wasn't and everything that Courageous has accomplished against the odds.

Social distancing is way more fun when it includes calling for room at the mark, so don your mask (on land) and come enjoy a day on the water! And, to make up for all the big races that weren’t in 2020, we’ll pack as much racing as possible into this one, aiming for a fleet of 20 boats, first gun at 1pm and racing straight through to 5pm

We are asking all participants to contribute whatever they are comfortable with, with a suggested minimum donation of $50/person or $100/team. If that’s not possible due to a Covid-related cause of any kind, that’s ok, just let us know. Our goal is simply to get people out on the water for a competitive event and a good cause. All donations will go directly to help us be there to support our Courageous kids through an extraordinary time.

Register Today!

  1. Make a Regatta Fee donation
  2. Register your team
  3. Fill out our waiver


  • Saturday October 3, 2020- 1pm-5pm
  • Rigging and check-in beginning at 12:30pm
  • First warning signal at 13:00 hours
  • Rain date: Sunday October 4, 2020

Race Documents