Join us on Saturday, August 9, 2025 for the FIFTH annual

SailMaine Festival & Regatta

PHRF Registration is OPEN! Click here for all the details.
J22/420 Registration will open in June!

The goal of this race is to raise money for SailMaine’s scholarship and community sailing programs. Our goal in 2025 is $80,000. Each boat is challenged with raising $250. (Folks can also create a fundraising team even if they do not want to race! All support is welcomed!)

Registration fee $100 - $25 late fee as of 8/1.

2025 Event Details

Event Schedule

Windward Exhibition

Celebrate Portland’s local artists!

Featuring a parade of painted sails, viewable from the SailMaine waterfront and our viewing outpost at Fish Point (below Fort Allen Park). Come by to watch the parade, stay longer and watch the whole race!

ARTIST APPLICATION


Festival & Regatta

  • Come out for a day of racing on beautiful Casco Bay and an after-party with food, music, and drinks to support community sailing (event schedule)

  • PHRF racing line, inner 420 & J22’s line, and HARBOR CRUISE!

  • Windward Exhibition: Saturday morning boat parade of painted sails by local artists and festival on Fish Point. Then stay to watch the racing!

  • Create your own boat team and be a top fundraiser! Compete as a racer and fundraiser!

  • Support an existing team or make your own fundraising page (even if you are not racing!)

Race and Registration Details

The goal of this race is to raise money for SailMaine’s scholarship and community sailing programs. Our goal in 2025 is $80,000. Each boat is challenged with raising $250*. (Folks can also create a fundraising team even they do not want to race! All support is welcomed!)

Notice of Race (lots of details!)

How does it all work?

First: Register to race (PHRF) or click here to register a 420 or J/22 ** Harbor Cruise click here!

Second: Create a fundraising page

Need help with your fundraising page? Check out our easy-to-follow instructions!

*420’s and J22’s/Harbor Cruise are asked to raise $100

**420/J22/Harbor Cruise registrants: DO NOT use Regattaman, just click the corresponding link above to register!

More details: