An Evening to Remember: The 2025 WoodenBoat Rendezvous

September 30, 2025

Each September, the Maine Windjammer fleet gathers in a secluded harbor for an extraordinary tradition: the WoodenBoat Rendezvous. More than just a meeting of vessels, it’s a celebration of Maine’s maritime community, where the coast’s most iconic schooners raft together and captains, crews, and passengers share an evening of music, community, and camaraderie. It’s an evening that proves wooden boats are not just history but a thriving part of Maine’s coast today.

The Rendezvous is the highlight of a longer sailing adventure. Guests spend several days aboard, exploring islands, quiet coves, and hidden harbors along the Maine coast. The rendezvous adds a rare dimension to that journey—an evening when the adventure expands into something communal. It’s not just a special night, but the centerpiece of an already unforgettable trip.

The setting makes it even more meaningful. Hosted in WoodenBoat Magazine’s harbor on Penobscot Bay, the Rendezvous unfolds at the very heart of wooden-boat culture. The campus is home to the magazine, which has chronicled the craft for decades, and the school, where new generations learn boatbuilding and woodworking. When the fleet assembles here, the legacy comes alive.

Part of the thrill is the arrival. One by one, schooners sail into the harbor, their sails glowing in the late-summer light. Bringing them close enough to raft is no small task. It takes quick line handling, clear communication, and a lot of trust between captains and crews. Watching that teamwork in action is half the fun. As each boat ties up, the fleet becomes a floating village, masts rising in a line against the evening sky.

Once the fleet is secure, the celebration begins. Guests can wander from schooner to schooner while the Bagaduce Music band moves through the raft, filling the air with bluegrass and folk tunes. On one deck, the music sparked a contra dance; on another, people sat tapping their feet and smiling as the melodies tied the fleet together in one joyful rhythm.

Guests also have the chance to hop in small boats and circle the raft, capturing photos and video in the golden evening light. This year after dinner, as the band continued softly and conversations drifted between decks, just as if on cue, the moon rose over the trees, washing the schooners in silver. It was the kind of moment that stays with you long after, woven into memory like the sound of rigging in the wind.