Giant Pumpkins Take to the Water for Damariscotta’s One-of-a-Kind Regatta

Damariscotta Pumpkinfest Regatta

If you’ve ever wondered whether a giant pumpkin can actually float, the Damariscotta Pumpkinfest Regatta has your answer. Every year, people hollow out massive pumpkins, climb inside, and race them down the Damariscotta River. It’s definitely not your typical boat race, and that’s what makes it so fun to watch.

Racing in Giant Pumpkins

The Regatta features both paddle-powered and motorized pumpkin boats. Racers squeeze themselves into hollowed-out pumpkins, often wearing crazy costumes, and try their best to make it across the water without tipping over. The paddleboats compete in individual and relay heats, while the event wraps up with a powerboat showdown between three longtime rivals: the Gnome, the Pirate, and Buzz.

Part of the fun is that these really are giant pumpkins being used as boats. Keeping one balanced while trying to race other pumpkins is obviously not easy, which makes things pretty unpredictable. Some racers move surprisingly well, while others are just trying to stay upright and avoid ending up in the river.

When and Where

The 2026 Regatta takes place Sunday, October 11, from 12:00–2:00 PM along the Damariscotta River. Spectators can watch from the harbor, and there’s also a live feed shown inside Lincoln Theater.

It’s weird, competitive, and honestly pretty entertaining, which is exactly why the Regatta has become such a popular tradition in Damariscotta.