Two weeks ago, the When And If returned home to Wiscasset harbor for the first time in 80 years to cannon salutes and cheers. The long blue trailing pennant that is only flown for a homecoming schooner flew high above the recreation pier for a long weekend celebration of art, music, boats and history. And it was magical.

The first ever Wiscasset Schoonerfest, Aug. 18-22, was a remembrance of the last of the four-masted schooners Hesper and Luther Little, and a celebration of the return of the When and If, General George S. Patton’s famous schooner, built in 1939 at F.F. Pendleton boat yard on White’s Island. And to honor them, 13 painted schooner silhouettes by local artists sailed grandly down the sidewalks of Main Street, delighting townspeople and visitors alike.

There hadn’t been that many schooners in Wiscasset for over 200 years.

Once upon a time, it was said, one could almost walk across the bows of ships from Wiscasset to Davis Island. But we were thrilled to have just a few special ones to explore: Fred and Mary Bowers’ Sycamore was berthed alongside the When And If, and the red sails of Alan and Judy Boyes’ Pagan Moon moored nearby. We all agreed, standing on the dock Friday night, with a full moon coming up behind the schooners in the harbor, and Pan Fried Steel Band playing on the pier … it was a moment straight out of Disney.

You’d swear the air sparkled.

A dozen bands and chantey stars entertained the crowds for three days on the pier stage and the bandstand on the town common. Harp, fiddle, flute and guitar provided intimate concerts in the town’s Sunken Garden. Saturday night a harbor full of boats lined up for a lighted boat parade, carefully navigating in the dark around a harbor full of lobster buoys. Sunday morning a first-ever triathlon hosted by Wiscasset Parks and Recreation went off without a hitch.

Who would have thought we could pull it off?

All told, about 1,200 visitors came through Wiscasset that weekend to enjoy the local bands, beer garden and boats. It was a huge success, even with the curtailed closing at noon Sunday with Ida bearing down on Wiscasset. As the When and If’s sails were hauled up for the last time, and her cannon fired off a departing salute, chantey masters Jerry Bryant, David Peloquin, Paula Daddio and a crowd of chanteyers sang a farewell from the dock, followed by a high soulful tune from Heather MacLeod’s tin whistle.

We had started late putting this festival together. It was May when COVID had finally slowed down, and we knew all events could be staged outside. We weren’t sure if we’d be overrun with crazed escapees from the other 49 states or if we were throwing a party and nobody would come. Turned out, the crowds were just the perfect size for our small town on the Sheepscot. Even the four-man crew of the When and If were impressed, telling folks at the Water Street bar that the people here were “the happiest we ever took onboard.” Coming from the experienced crew out of Salem, Massachusetts, that was pretty high praise, and we were proud of our hometown.

We planned an all-local festival. Food trucks—Pittston’s smoked meats by Smokin’ Grandpa, and Wiscasset’s Brother Shuckers oysters — lined up at the pier next to the wine and beer garden, hosted by the popular Water Street Kitchen and Bar. And thanks to the kindness of pier shack owner Theresa Gray, Sarah’s Scoops from next door in Boothbay Harbor served up the ice cream. Everybody came back for more. Nobody starved.

And we worked in a little historic mayhem that was huge fun — even a good thing. The 1800s-costumed 3-man drama troupe from Wiscasset Middle High School regaled crowds on the pier and Main Street with funny readings of the Wiscasset Shillings Laws from 1822. Then Russell, Evan, and Leo enthusiastically handed out tickets to law-breakers for disturbing the peace. They even nabbed Chief Hesseltine for improperly crossing a line. All fines went to the Class of 2022 graduation fund.

Special thanks to Police Chief and Harbor Master Larry Hesseltine, Wiscasset Parks and Recreation Director Duane Goud and Chelsea Taylor, Public Works Director Ted Snowden, Wiscasset Yacht Club, Town Manager Dennis Simmons, a wonderful crew of 45 volunteers, and a great team of National Guardsmen out of Augusta who volunteered their time for trash detail and tent take-down. And a huge thank you to the lobstermen, diggers and boat owners who put up with a temporary take-over of half of the pier area. We couldn’t have done it without their patience, and it was much appreciated.

Also many thanks to Lang Sheppard for his masterful documentary of the event, aired on LCTV and available at https://vimeo.com/597224335

Readers can still access WiscassetSchoonerfest.com to find the first 27 business partners who joined another 50 individual sponsors of this event. We are grateful for the tremendous support of this community. We broke even, but folks can still donate for next year!

We have to say, the first ever Wiscasset Schoonerfest was the GOAT! Bring it on for the second annual in 2022!

The 2021 Schoonerfest Steering Committee – Peter Wells, Dan Watts, David Pope and Terry Heller