Sailing Season 2019 on Penobscot Bay: races, regattas and parades

Tue, 07/02/2019 - 1:30pm

Penobscot Bay is among the best cruising grounds in the world, sailors agree. Prevailing summer breezes out of the southwest, safe harbors and beautiful water make it all so. Then there are the races — some highly competitive; others, well, it’s all about the boats and having a good time. 

Below is a list of the larger events, but local yacht clubs are also busy with their smaller races and regattas. Visit websites for updated schedules: Camden Yacht Club (, Northport Yacht Club (, Rockland Yacht Club (, Bucks Harbor Yacht Club (, Castine Yacht Club (

2019 racing and regatta schedule

July 4, Retired Daysailor Skippers Race
Thursday July 4, Northport Yacht Club, 3 p.m.
July 5, 43rd Annual Great Schooner Race
Maine’s tall ship fleet gathers for an exciting race from Islesboro to Rockland, followed by a festive Awards Ceremony/Party with live music. Good viewing from the shore is the Rockland Breakwater, with vessels anticipated to sail into Rockland Harbor between 2-4 p.m.
Pre-Race festivities include small boat races.

July 12, Maine Windjammer Parade of Sail
The entire windjammer fleet participates in an afternoon Parade of Sail past the mile-long Rockland Breakwater, providing spectators with close-up views of Maine’s fleet of tall ships, 2-4 p.m.

July 25-27, Camden Classics Cup, hosted by Lyman-Morse at Wayfarer Marine, 9 a.m. The Camden Classics Cup is a two-day regatta that opens the classic sailboat racing season in Maine. The Cup is the anchor event of Camden Classics Week, a week of destination racing to and from Castine, Brooklin, and the outer islands. The Camden Classics Cup is a celebration of both classic yacht racing and boatbuilding.

Aug. 1, Castine Classic Yacht Race to Camden, hosted by the Castine Yacht Club. This year will honor designs of Nathanael G. Herreshoff. On July 31, Herreshoff craft will be on exhibition at the Castine town dock, followed by a symposium at Maine Maritime Academy with a panel of Herreshoff experts and sailors, chaired by Bill Lynn, executive director of the Herreshoff Marine Museum/America's Cup Hall of Fame. The Castine Yacht Club will host a reception following the symposium. Mystic Seaport Museum will present to Ben Mendlowitz its prestigious William P. Stephens Award in recognition of his significant and enduring contribution to the history and appreciation of American yachting.

Aug. 3, Eggemoggin Reach Regatta
The Eggemoggin Reach Regatta began humbly in 1985 with 13 wooden boats and a dream for wooden boat owners to get to together and enjoy each others company, as well as compete. The race quickly grew to 125 boats and is now co-hosted by Brooklin Boatyard and Rockport Marine. The Regatta's 15-mile course has remained the same over the years and only once was the race cancelled due to fog. (The party still happened though!) The Camden Feeder Regatta and the Castine Classic Yacht Race soon joined the ERR to create the three-day event.

Aug. 10, Monhegan Regatta, hosted by the Portland Yacht Club, 9 a.m.
OK, so this is not technically Penobscot Bay, but the competitive race streams by on the waters just to the southwest with gorgeous boats from Portland to Monhegan. The focus is on endurance, navigation and strategy, as well as speed.

Aug. 17, Maine Retired Skippers Race, hosted by Maine Maritime Academy, Castine, 9:30 a.m.
The historic race, annually since 1952, is fun and competitive. The retired skippers, age 65 and older, are not to be tangled with on the 12-mile course on East Penobscot Bay.

Aug. 30, Camden Windjammer Parade
11:30 a.m. to 3 p.m., Camden Windjammer Weekend Parade of Sail to Camden Harbor for Windjammer Weekend.

Sept. 7, Around Islesboro Race, hosted by the Northport Yacht Club, 9 a.m.
Thirty-four years old now, the annual race signals that colder weather looms, and it is a blast for all classes of boats.

Sept. 10, Woodenboat Gathering, Brooklin
The fall gathering of the fleet takes place in Brooklin, headquarters of WoodenBoat Magazine and WoodenBoat School. Now in its 33rd year, the event includes refreshments, live music, tours and a harbor full of historic schooners.

Sept. 14-15, Maine Rocks Race, hosted by Rockland Yacht Club, 9 a.m.
This is a long race, 122 nautical miles from Rockland to Matinicus Rock, over to Mt. Desert Rock, then back to Matinicus and Rockland. Phew! It’s endurance and skill, and serves as a qualifier for the Ocean Planet Short-handed Trophy.