2nd Annual Connecticut Sea Music Festival

Essex Town Green Essex Street, Essex, CT

The 2nd Annual CT Sea Music Festival will drop anchor in downtown Essex on June 9-12, 2023.   This family-friendly weekend includes a Symposium on the Music of the Sea, free daytime workshops with local, regional, and international maritime musicians, a family stage, demonstrations of sailor skills, sails on theRead More

$15 – $25

Boothbay Harbor Yacht Club Regatta and Shipyard Cup Classics Challenge

Our first two combined Shipyard Cup Classics Challenge/Boothbay Harbor Yacht Club Annual Regattas were huge successes.  This year is promising to build on that momentum.   Boothbay will again offer great competition, a true on-the-water spectacle, and noteworthy social events (the regatta’s Saturday evening reception at Bristol Marine’s Shipyard atRead More

3rd Annual Pacific Seacraft GAM

Seal Bay Vinalhaven Island Vinalhaven, ME

Are you an owner of a Pacific Seacraft sailboat?  You are invited to join in the 3rd annual Pacific Seacraft GAM in Seal Bay Vinalhaven Maine on July 22/23. Last year 10 of these beautiful boats came to the scenic anchorage with owners and crew socializing and exploring the area. InRead More

Camden Classics Cup

The Camden Classics Cup is one of the world’s most beautiful regattas - sailed where the mountains meet the sea off the lovely harbortown of Camden, Maine.   The Camden Classics Cup aims to give sailors the time of their lives with terrific on-the-water racing, and stellar onshore events. PresentedRead More

Downeast Challenge

Marblehead Yacht Club 4 Cliff Street, Marblehead, MA

Downeast Challenge is an exciting 90 mile long distance overnight sailboat race from Marblehead to Portland, ME. Crewed and Shorthanded boats welcome. Rising Tide Brewing and Rumson's Rum sponsor the skippers meeting and Award party at Fore Points Marina, Portland. Free T-shirts for skippers and for sale to crew.

$55 – $75

Monhegan Island Race & Seguin Sprint

Portland Yacht Club 40 Old Powerhouse Road, Falmouth, ME

One of the longest standing Ocean Races, the Monhegan Island Race began in 1928. This 4 day event now consists of two races; the Monhegan Island Race which is 140nm and the Seguin Sprint which is 50nm, one hell of a kick off party, and culmination with an epic breakfastRead More

$195 – $550

Maine Boat & Home Show

Harbor Park 1 Pleasant St., Rockland, ME

The Maine Boat & Home Show is back, August 11 - 13, 2023. If you love the coast of Maine, you won't want to miss this high-end, high-summer event in Rockland, Maine, the second weekend in August. The show features boats in the water, boats on land, marine supplies, fineRead More


SailMaine Regatta & Festival

Join us for the 2023 SailMaine Festival, a fun and exciting event taking place Saturday, Aug. 12, in Portland Harbor, featuring a colorful parade of boats flying painted sails by local artists, a regatta for junior sailors right off Portland's east End and a Performance Handicap Racing Fleet Challenge inRead More

RYC Scholarship Regatta

Rockland Yacht Club 1 Harbor Park, Rockland, ME

The Rockland Yacht Club’s (RYC) annual Scholarship Race will take on a new dimension in 2023 by partnering with the Sail, Power & Steam Museum to help raise funds for educational opportunities for youth sailing programs in Midcoast Maine. Scheduled for August 19, 2023, all yachts are welcome to participate.Read More

$100 – $125