Vintage Boats Take Center Stage at Boothbay Harbor Windjammer Days This Week

The Schooners Bowdoin and Heritage sail in Boothbay Harbor. Photo/Boothbay Windjammer Days.

Classic craftsmanship, maritime history, and Maine coastal charm will be on full display when the Annual Vintage Boat Parade returns to Boothbay Harbor as part of the 64th Annual Windjammer Days celebration.

Tug-of-War is one of the many events that go on during the event. Photo/Boothbay Windjammer Days.

Held in Boothbay Harbor, Maine, Windjammer Days has been celebrating the region’s maritime heritage since 1962 and remains one of New England’s premier waterfront festivals. This year’s event runs June 21-27 and features everything from schooner gatherings and harbor parades to lobster competitions, fireworks, and family-friendly activities.

For boating enthusiasts, one of the week’s signature events is the Annual Vintage Boat Parade, scheduled for Friday, June 26 at 4 p.m. During the parade, vessels more than 25 years old will cruise through the inner and outer harbor, giving spectators a rare opportunity to see beautifully preserved wooden boats, classic cruisers, and historic recreational craft underway. An announcer will provide commentary as the boats make their way through the harbor.

The parade reflects the enduring appeal of antique and classic boats throughout New England, where generations of boat-builders and owners have worked to preserve the region’s rich maritime traditions. Catch a glimpse of gleaming mahogany runabouts, lovingly restored wooden yachts- these vessels represent a time when craftsmanship and design were as important as performance on the water.

The vintage boat parade is just one highlight of Windjammer Days. Throughout the week, visitors can enjoy the Gathering of the Fleet as historic schooners arrive in Boothbay Harbor, a decorated boat parade, live music performances, maritime exhibits, pirate-themed activities, waterfront competitions, and a spectacular fireworks display over the harbor.

For boaters, anglers, and maritime history enthusiasts, Boothbay Harbor offers an ideal setting. The protected harbor, scenic islands, working waterfront, and longstanding connection to Maine’s boatbuilding industry make it one of the state’s most iconic boating destinations. Windjammer Days serves as both a celebration of that heritage and a reminder of the important role recreational and commercial boating continue to play along the New England coast.

Arriving by land or sea? The Vintage Boat Parade provides a unique opportunity to experience classic boats where they belong—on the water—surrounded by one of New England’s most picturesque harbors.

Written by Zavia Walker

Watching some of the many schooners in the harbor during Windjammer Days. Photo/Boothbay Windjammer Days.