Damariscotta Pumpkinfest Regatta

Pumpkinboat Building

Saturday, October 10, 2026 (9:00 AM - 11:00 AM)

Location: Louis Doe Home Center 92 Mills Road Newcastle, ME, 04553 United States (map)

Come see the masters at work assembling pumpkinboats for the upcoming regatta race!

Sponsors: Hancock Lumber/Louis Doe Home Center

 Regatta

Sunday, October 11, 2026 (12:00 PM - 2:00 PM)

Location: Damariscotta Municipal Parking Lot (map)

The Regatta is a Beloved Pumpkinfest Tradition

Brainchild of Bill Clark and Buzz Pinkham, the Regatta has long been a fan favorite. When asked where the idea of turning a giant pumpkin into a boat originated, Buzz mentioned: What else would you do with a 750 pound pumpkin? The Regatta is truly a highlight of what we do with big pumpkins here in Damariscotta, and is one of the anchor events (pardon the pun!) of our festival. The Regatta takes place when high tide allows each year. We really do hollow out our pumpkins with the best 'hull lines,’ wear zany costumes, wedge ourselves inside, and paddle or motor on the Damariscotta River in front of thousands of enthusiastic spectators.

Described as the “extreme sport of gardening,” this real-life jack-in-the-beanstalk sport is an event you don’t want to miss! Spectators will be thrilled to watch giant gourds -steered by captains either paddling or powered by “wicked nice motors”- ply the waters of the Damariscotta River in a series of races.

Pumpkinboat Regatta consist of paddleboats racing in 2 or 3 individual heats and 2 or 3 relay heats. Spectators always look forward to The “feature” relay, in the past we have had the Maine Cabin Masters, Maine TV Weather people and this year will feature surprise guests.

The grand finale features the annual showdown between our three long-time pumpkin powerboat rivals: the Gnome, the Pirate, and Buzz.

The regatta can be viewed harbor-side, or via a “live feed” into The Lincoln Theater, where spectators are able to watch the event, seated in the warmth and comfort of the historic theater.

Get Involved!

Our prime objective is to put on a fun and exciting spectacle for the crowd gathered along the shore. Many of the Pumpkinboat pilots have been part of the event since the very beginning and return every year, not only because they have a blast, but also because they know how to keep their 'boats' upright and in race trim. Keeping a giant pumpkin from becoming a giant bathtub of chilly river water is no easy feat! New paddlers are welcome as space allows, too, and may express interest by filling out the form below.