Boothbay Harbor’s beloved Windjammer Days celebration is set to bring even more intrigue to the waterfront this year as the annual Vintage Boat Parade & Pier Party returns with a new twist: a series of Haunted Maritime Stories presented by Mysterious Harbor Tours. The addition blends local folklore with the region’s deep nautical heritage, adding a new experience to one of the festival’s most anticipated traditions.
The Vintage Boat Parade will once again showcase a fleet of classic vessels, each at least 25 years old with newer boats leading the procession, while the oldest and most storied vessels will make their entrance last. Announcers stationed in Whale Park will share details about each boat as it passes, turning the parade into a narrated journey through maritime craftsmanship.
Following the parade (which is free and can be watched from anywhere in the harbor) is the annual Pier Party held at Bristol Marine’s Sample’s Shipyard. This is a ticketed event where ticket holders will enjoy appetizers and a full cash bar. Live music from The Wharf Cats will set the tone for the evening, and the shipyard will once again host a curated display of vintage motorcycles and classic cars, creating a cross‑section of mechanical artistry on both land and sea. Mysterious Harbor Tours, known for their popular storytelling walks and e-bike tours, will bring to life legends of shipwrecks, phantom lights, and sailors whose stories never quite made it into the history books.
The goal of this event is to honor the region’s maritime legacy while giving visitors and residents a chance to experience Boothbay Harbor’s maritime history from new perspectives. “These boats carry decades of stories,” Bruce White, committee chair noted. “Adding the haunted maritime tales felt like a natural way to celebrate the history, the mystery, and the character of this harbor all set to the backdrop of a 186 year old shipyard.”
Tickets for the Pier Party are limited and expected to sell quickly. With the combination of historic vessels, live entertainment, and the debut of maritime ghost stories, this year’s event promises to be one of the most memorable in Windjammer Days history.
Tickets are $65/person - the same as last year - and includes entry to the Pier Party and one drink ticket (wine/beer or soda). A full cash bar will be available, and credit cards are accepted. Please note that tickets need to be purchased online BEFORE arriving at the event.
