Boothbay Harbor Windjammer Days June 23-29

Sun, 06/09/2024 - 4:00pm

Windjammers. When you hear or read that word, what do you see?  Majestic vessels whose sails billow as the vessels gracefully sail across the ocean below a blue sky and brilliant sunshine?

But they are just as majestic in rain and fog; the three harbor-bound windjammers Capts. David and Marion Dash came upon in 1962 were, and caused quite a sensation in the town, too. The Dashes were so impressed by them, they decided there ought to be an occasion to celebrate these windjammers and the important role they have played since the 19th century. These traditionally rigged vessels are two-masted schooners or three-masted barquentine (schooners with three or more masts with the foremast square-rigged and the others fore-and-aft rigged). 

The first Boothbay Harbor Windjammer Day was held July 10, 1963. Schooners Victory Chimes, captained by Boyd Guild out of Castine; Mary Day/Capt. Havilah Hawkins out of Sedgewick; Mattie and Mercantile/Capt. Jim Nesbitt out of Camden; Tabor Boy/Capt. George Glaesar; and Richard T. II/captained by David Dash, who served as chairman of the first official event. The schooners rendezvoused at Squirrel Island and sailed into the harbor, greeted by hundreds of people along the shoreline, on boats and in the harbor.

Over the decades, Boothbay Harbor Windjammer Day grew to a two-day festival, then four when there was also a Windjammer Days golf tourney fundraiser for Special Olympics. Since the Friends of Windjammer Days group has been at the helm since 2013, it has grown into a seven-day event that remains as popular as ever. For a full history, visit the Boothbay Register’s Windjammer Days page via the home page of the website.

This year, 16 windjammers plan to attend the 62nd festival. A Morning in Maine, Malabar X (10) – a first-timer, American Eagle, Pilot Cutter Hesper, Harvey Gamage, Isabella, Alert, Sycamore, Eagle, Virginia – Maine’s First Ship, True North, and the Thomas E. Lannon. Four windjammers, Eastwind, Applejack, Tyrone, Isaac H. Evans and the yacht Gleam, call Boothbay Harbor their home port.

Local boat companies offer special trips on the Tuesday (June 25) and Wednesday (June 26) of every Windjammer Week.

Competitions are longtime crowd pleasers Boothbay’s Got Talent; cod fish races, lobster eating contest, rock skipping, the tug across the harbor, and sailboat races. What about parades? There’s the vintage boats (plus a fun pier party with appetizers, cash bar and music and, new this year, an antique car show after the parade), the street parade with floats, music including the Sailing Masters of 1812, a fife and drum corps hailing from Essex, Connecticut; antique vehicles, Kora group acts, clowns, stilt-walkers, and more. One year, there was a flash mob of dancers once the parade was in the downtown area! Such fun! And, of course, the Gathering of the Fleet (formerly Parade of Sail) when the Windjammers sail into the harbor and drop anchor for a bit. 

This year, there’s great news for the youngsters: the Maine State Aquarium is reopening. From 10 a.m. to 4 p.m., there will be all kinds of fun happening there once again. Other kid-related activities include Windjammers For Wee Mateys and an old-time carnival at the Library, Kids Alley and much mayhem and laughs with the Pirates of the Dark Rose. 

Art lovers won’t want to miss the two-day Artists Alley, fans of the supernatural will want to go on one of the tours by American Ghost Walks; then there’s the lighted boat parade (since 2015), and the Blessing of the (commercial) Fleet. Stage entertainment includes Maine’s Tim Sample at the Opera House; and at Carousel Music Theater, the Boothbay Summer Theater production, “My Witch: The Margaret Hamilton Stories,” – Hamilton was a seasonal resident here beginning in the early 1960s on Cape Island. And, weather permitting, the traditional fireworks display lights up the sky.

For a full list of events – yes, there are more – you have several options: At the Boothbay Register, 97 Townsend Ave., Boothbay Harbor, get a copy of the Windjammer Day Guide the Register has produced for over 30 years; or get a copy at lodgings and other local businesses; the Tuesday and Wednesday of the Festival, there will also be some at the Friends of Windjammer Days tent on the waterfront; or visit the official Festival website:, or the Boothbay Register’s Windjammers Days page via the Boothbay Register and Wiscasset Newspaper websites’ home pages.

See you ’round the waterfront!