Weekly Racing Series

Passholders and their guests can join our weekly races at no extra charge. Races are held on Thursday evenings at 6:00pm throughout the Summer season as the weather allows. As the Summer turns to Fall, we change to racing on Sunday mornings.

We love to educate new participants on the rules of racing, but still actively work to keep the competition friendly and casual.

Races Around the Harbor Islands

Each season, PPSC hosts races that incorporate the Boston Harbor Islands as part of the course. Boats start as a group directly in front of Piers Park’s cove, follow a course around Spectacle or Long Island, paying close attention to buoys as waypoints, and finish in the same location of the start. These courses range between 10-15 miles long, making for a great day sail even for those who aren’t feeling particularly competitive. 

The Soup to Knots Regatta is a Harbor Island race where PPSC collects registration fees to benefit the East Boston Community Soup Kitchen. We’ll give out PPSC merch as prizes along with presenting an engraved cup to the winning boat! All PPSC Passholders and their guests are welcome to join this race in order to make the largest impact possible.  

We finish each sailing season on October 31st, so we celebrate with a final race around the islands, The Halloween Howl. Participants are encouraged to wear costumes for a chance to win prizes. The entire PPSC fleet will seemingly take over the harbor while most other boaters have already retired for the season. 

Email the Race Committee at racing@piersparksailing.org to opt in to weekly race emails that include race sign ups and special announcements!