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A look back at 2019 and a look forward to 2020

While the 2019 Maine Windjammer Association season is still underway, with plenty of opportunities for fabulous fall sailing through mid-October, we’ve wrapped up the fleet-wide events for the season.  From the Gam to the WoodenBoat Sail-In, the fleet gathered from Carter Cove to Camden and ports in-between for raft-ups and races. It’s not too early to reserve your spot at these events in 2020.  Many of these fleet-wide events are popular and sell out, so make your plans and reservations early for these fabulous events in 2020.  Reserve ahead directly with your favorite windjammer.

The Maine Windjammer Association is the largest fleet of working windjammers in America. When they gather for fleet-wide events participants and spectators are treated to a slice of history that’s simply unmatched anywhere else.  Watching these lovely vessels sail in and then gather into a “mass of masts” with all the rigging and flags is a sight to behold.  Those who are lucky enough to participate or spectate are often awed by the historic significance of so many national historic landmarks gathering in one place.  From the oldest windjammers in America, to the only working three-masted windjammer and the newer windjammers too, looking up at all that rigging is impressive.

A view of the rigging from windjammers gathered at the annual Gam hosted by Maine Windjammer AssociationA view of the rigging during the annual Gam raft up.  Maine Windjammer Association photo.

The toast offered during the annual Gam raft-up creates a positive omen for the season.  This year, the toast was followed by an evening musical jam with the Stephen Taber Band, aka the Charlie Nobles joined by musicians from all the boats.  We like to call this a “gam jam”.

Captains gather on Victory Chimes to give the annual toast of the season at the Gam. Captains gathered on Victory Chimes to offer the annual toast to the season. Maine Windjammer Association photo.

Captains and crew gather on the Victory Chimes for a jam session. Crew and Captains join the Charlie Nobles on board the Victory Chimes to offer a “gam jam”.  Maine Windjammer Association photo. 

Not too long after the Gam, the crew gathered over July 4th weekend for the annual Great Schooner Race.  This year a number of new boats joined the race, including the impressive Columbia from Florida.  The Great Schooner Race is always kicked off with the annual wacky Small Boat Races, filled with zaniness and costumes, and this year was followed by a beautiful sunset. On race day, the Great Schooner Race started out in light wind, but ended in a nail-biter of a finish, with the Schooner Mary Day squeaking out a first place win over Columbia on corrected time.

Small Boat Races - crew of J&E Riggin got Best Spirit Award for their July 4th costumes.

Winners of the “Best Spirit” award for their costumes to celebrate July 4th in the Small Boat Races.  Andy Castillo/ photo.

Sunset in Islesboro with Maine Windjmammer fleetThe sun sets over Victory Chimes as boats throughout the fleet get ready for the big race the next day.  Maine Windjammer Assoc photo.

Boats gather at the start line of the Great Schooner RaceBoats gather at the start of the 43rd Annual Great Schooner Race. Photo by Bob Trapini.

Great Schooner Race 2019 - boats underwayAnd they’re off!  Boats underway right after the start of the Great Schooner Race.  Photo by Richard Ball.

Captain Jim Sharp congratulates Capt Barry King on his Great Schooner Race winCaptain Jim Sharp congratulates Schooner Mary Day captain, Barry King, on his first place in at the 2019 Great Schooner Race.  Maine Windjammer Association photo.

Unfortunately, rainy weather caused the annual Parade of Sail to be cancelled this year.  Sadly, Mother Nature shrouded Rockland Harbor in a blanket of fog and rain, making it too difficult for people to walk on the Breakwater and impossible to see the boats. We look forward to sunnier weather in 2020 for this impressive gathering of windjammers from throughout Penobscot Bay.

Moving forward through the season, the next gathering of the fleet was in Camden Harbor during the Annual Camden Windjammer Festival.  A celebration of windjammer history, this event traditionally attracts thousands of people to enjoy a parade of sail, the annual windjammer dinner auction, talent show and fireworks over the harbor.  The mass of rigging seen over Camden Harbor is so impressive! For those who love windjammers and nautical history, this is a fabulous event.  Captain Jim Sharp, windjammer expert,  narrates the parade of the boats into the harbor with such entertaining stories.

Maine Windjammer Association booth at Camden Windjammer FestivalMaine Windjammer Association booth where dinners on the schooners were auctioned off and gear bags are raffled.  Maine Windjammer Association photo.

View of windjammers in Camden Harbor during the Camden Windjammer FestivalView over the harbor of boats gathered for the Camden Windjammer Festival.  Maine Windjammer Association photo.

Captains gather at Camden Windjammer Association by the Harbormaster's house. Camden Harbormaster, Steve, offers a toast to the Maine Windjammer Association captains for a great season.  Maine Windjammer Association photo.

Oscar Barnes playing ukulele during the Schooner Talent Show at Camden Windjammer Festival 2019Oscar Barnes, crew member on the Schooner Stephen Taber took second place honors in the Schooner Talent Show during the 2019 Camden Windjammer Festival.  Photo by Jim Dugan.

Crew of Lewis R. French on stage at the Schooner Talent Show, Camden Windjammer Festival, 2019The crew of the Lewis R. French celebrate their first place win at the Schooner Talent Show. Photo by Jim Dugan.

Friday night fireworks over Camden Harbor during the Camden Windjammer Festival with Schooner Mary Day in the foreground.  Photo by Jim Dugan.

The final fleet-wide of the year always takes place on the second Tuesday in September.  It’s a sail-in when windjammers gather at WoodenBoat School in Brooklin to enjoy mussels, hor d’oeuvres and the calypso tunes of the Flash in the Pans Steel Drum Band.  We were blessed with great weather this year and beautiful views of the Maine Windjammer Association ships sailing into the harbor in Brooklin.

Photo of windjammers gathering at WoodenBoat School.

Onlookers are treated to a view of the entire Maine Windjammer Association fleet, gathering for the WoodenBoat Sail-In at WoodenBoat School. Maine Windjammer Association photo.

Two women smiling and standing behind the hors d'oeuvres table at WoodenBoat Sail-InAlisa and Dede, from Maine Windjammer Association, pose just before guests arrive for mussels and hors d’oeuvres. Maine Windjammer Association photo.

Captain Linda Lee enjoys steamed mussels at the WoodenBoat Sail In

Captain Linda Lee of the Schooner Heritage takes a break to enjoy steamed mussels and hors d’oeuvres, along with music provided by Flash in the Pans Steel Drum Band.  Maine Windjammer Association photo.

People dancing among the picnic tables to the tunes of Flash in the Pans Steel Drum Band at WoodenBoat Sail-In. Tunes from the Flash in the Pans Steel Drum Band got everyone up and dancing during the WoodenBoat Sail-In.

Sunset over windjammers gathered at WoodenBoat Sail-In. People watch from the dock. The sun sets over the fleet as passengers gather to head back to the boats after the traditional mussel feed at WoodenBoat Sail-In. Maine Windjammer Association photo.

That concludes our armchair journey through the fleet events of 2019.  Aren’t you ready to be a part of one or more of these events in 2020? You’ll find each vessel’s 2020 cruise schedule on their individual websites or on the search tool found on the’s home page (click on 2020 cruises).

Categories: Cruises, Maine Windjammers, Sailing Events

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