Join us on Saturday, August 9, 2025 for the FIFTH annual
SailMaine Festival & Regatta
Registration opens NOVEMBER 22, 2024! Click here for all the 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 if they do not want to race! All support is welcomed!)
Registration fee $100 - $50 discount before May 1. $25 late fee as of 8/1.
Details below are from 2024 for reference; 2025 info coming soon!
2024 Event Details
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! SailMaine waterfront will host an activity center; kids can build and decorate their own boats!
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 NEW this year: 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!)
Our top fundraiser will be presented with this fabulous painting by award-winning local artist Maggie Daigle!
“Final Tack”
by Maggie Daigle
11”x14” acrylic on canvas in maple float frame
Maggie Daigle is an award-winning Maine painter with a loyal following for commissioned landscapes and animals portraits. She is an exhibiting member of Gallery 302 in Bridgton – one of the oldest artist co-ops in Maine. It’s there she teaches painting classes and shows her work year-round. Maggie and her husband Bob are lifelong sailors who left their corporate jobs in 2010 to spend six years working aboard and chartering sailboats. When they returned to Maine, they built their house in Casco, in the western lakes region. They split their time between country life and cruising and racing on Casco Bay aboard their 1972 C&C 35’ sloop, “Decoy.” This is the third year Maggie has donated a painting to SailMaine’s Festival & Regatta. She says she takes much of her inspiration for the SailMaine paintings from the beautiful photographs taken by her friend, the late, great Valentine’s Day bandit, Kevin Fahrman, who photographed the SailMaine fleet for many years. To see more of Maggie’s work, go to her website www.maggiedaigle.com.
Race and Registration Details
The goal of this race is to raise money for SailMaine’s scholarship and community sailing programs. Our goal in 2024 is $70,000. 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 420/J22 ** Harbor Cruise click here!
Second: Create a fundraising page
*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:
