North America’s oldest annual schooner race returns to Rockland Harbor for the Great Schooner Race Friday, July 8, providing spectators with easy-viewing access along the mile-long Breakwater.

On July 8 at 10 a.m., more than a dozen schooners will race from Gilkey Harbor on Islesboro to the Rockland Breakwater, where their dramatic mid-afternoon arrival will recall the days when cargo-laden schooners raced to be the first to Rockland so they might capture the best market prices. A century ago, every schooner trip was a race against time and a captain’s profits depended heavily on his crew’s sailing skills.

Since 1977, any traditionally rigged schooner on the Eastern Seaboard has been welcome to participate in the Maine Windjammer Association’s Great Schooner Race held in Midcoast Maine. Known as an extremely informal and friendly competition, the captains have often let wind, weather and tide dictate the Race start and finish, but recent efforts to make the event more accessible have brought the event back to the Rockland Breakwater Lighthouse.

Rafting up for the night in Gilkey Harbor, on Thursday, July 7, the captains will conduct small boat races and other friendly maritime competitions amongst Race participants. Race Day will begin with a Captains’ Meeting aboard Maine’s largest windjammer — the Victory Chimes. There, they will set the day’s race course and classes.

Many of the participating schooners are National Historic Landmarks, while others were built in the last century specifically for the windjamming trade. All of them are beautifully maintained maritime treasures. Spectators can cheer for their favorite schooner from the Breakwater that marks one end of the finish line.

An evening ceremony at the Sail, Power and Steam Museum for participants will feature a presentation of awards plus festivities.

For more information about the 40th annual Great Schooner Race, contact the Maine Windjammer Association, 1-800-807-WIND or visit