Maine loves its schooners and beautiful sailboats. Enjoy these spectacular summer sails from onboard or onshore. The various Midcoast harbors have their own boat and yacht clubs with local races taking place through the season. The following represents some of the bigger regattas and races scheduled for Summer 2025. 

June 21, Rockland Solstice Race
Since the late 1990s the Rockland Yacht Club has held an annual race on the Saturday closest to the longest day of the year. Aptly named the Solstice Race, this event is held around government marks in West Penobscot Bay. Racers can look forward to friendly, spirited competition, and a chance to knock the rust from sailing skills and reflexes dulled by long Maine winters. rocklandyachtclub.org

June 26 – 28, Windjammer Days
This year marks the 63rd annual Windjammer Days in Boothbay Harbor and marks the kick off to summer in the Boothbay region.

July 4, Great Schooner Race
Maine’s tall ship fleet gathers for a race around Penobscot Bay. Every summer since 1977, the Maine Windjammer Association has hosted the Great Schooner Race, providing an opportunity for captains, crews and passengers aboard traditional vessels from all over the Eastern Seaboard to rendezvous for a fun day of racing. greatschoonerrace.com

July 24-26, Camden Classics Cup. Where the mountains meet the sea in Camden. The Cup give sailors the time of their lives with terrific on-the-water racing, and onshore events. Presented by Lyman-Morse with support from the CYOA. camdenclassicscup.com

July 31, Castine Classic Yacht Race, Castine Harbor. classicyachts.org

July 31–Aug. 3, 94th Monhegan Island Race and Seguin Island Sprint. Starts at Portland Yacht Club. A test of patience, strategy, tactics and seamanship, this race is Maine’s premier overnight event. monheganislandrace.org/

Aug. 1, Camden to Brooklin Feeder Race
38th annual Camden to Brooklin race departs Camden Harbor and charts a course through Penobscot Bay in time for the annual Eggemoggin Reach Regatta. classicyachts.org

Aug. 2, Eggemoggin Reach Regatta. This regatta brings out the wooden boat beauties of Maine and their gorgeous designs. It is the largest wooden boat regatta in the world, it is said. Penobscot Bay yacht clubs usually hold a feeder race to the annual Brooklin gathering, running a 19.6 mile course from Castine to Camden, followed by a Camden to Brooklin race, culminating in the Wooden Boat Regatta. camdenyachtclub.org

Aug. 29 – 30, Camden Windjammer Festival
The fleet gathers in picturesque Camden Harbor for festivities reminiscent of the days when hundreds of coastal schooners lined the waterfront. Festivities include a parade of sail, flag-raising ceremonies, live music, dancing and fireworks.

Sept. 6, Around Islesboro Race
Organized by the Northport Yacht Club, the Around Islesboro Race is a fun and friendly regatta. The biggest Maine Regatta held anywhere north of Portland is also the most fun.  The race starts in front of the Bayside dock, circumnavigates 10 mile long Islesboro Island and returns to Bayside .  The course is over 26 nautical miles as the crow flies.  The direction to take around Islesboro is decided the morning of the race based on wind direction and the timing of the tides in Gilkey Harbor. northportyachtclub.org

Sept, 9,  Wooden Boat Sail-in (Rende-vous)
The late summer gathering of the fleet takes place in Brooklin, headquarters of WoodenBoat Magazine and WoodenBoat School. The Maine Windjammer Association vessels sail into Brooklin and is a great opportunity to see all the windjammers up close under full sail. Guests can go ashore to visit the Wooden Boat campus and enjoy live music and refreshments.

Sept. 13-14, Maine Rocks Race
The Maine Rocks Race is a short-handed race of over 100 nautical miles. This race is a test of endurance and seamanship, offering participating sailors the opportunity to sharpen their short-handed offshore sailing skills and refine systems and procedures for short-handed passage-making. rocklandyachtclub.org