Windsor Pumpkin Regatta: A Nova Scotia Original (1999-2019)

Update, October 2026: the Windsor Pumpkin Regatta is off indefinitely. The world's original giant-pumpkin boat race, founded in 1999 by Windsor grower Danny Dill and his family, last ran on Lake Pisiquid in October 2019. After two pandemic cancellations, a 2022 provincial order changed the Avon River tidal gates to restore fish passage and permanently lowered the lake the course depended on, and no revival has been announced since.

For twenty years it was one of the continent's strangest spectator days: paddlers climbed inside hollowed Atlantic Giant pumpkins and raced them across Lake Pisiquid, with a parade through downtown Windsor and the growers' weigh-ins around the racing. Windsor's claim as the world's first giant-pumpkin regatta dates to 1999, when local growers first paddled giant gourds for the far shore, and the free family spectacle put the town firmly on the weird-events map. Windsor's fall calendar still earns a trip: the Windsor Hants County Exhibition opens the season, the Kentville Pumpkin People Festival runs down the Valley in October, and the South Shore's Mahone Bay Scarecrow Festival fills the same weeks - build the weekend with our fall trip planner.

The tradition lives on: since 2022 the giant-pumpkin regatta paddles out of Shelburne on the South Shore - the Nova Scotia Giant Pumpkin Festival and Regatta (Oct 10, 2026) is the race to plan a trip around, with the weigh-off, carving, and harbour course on Dock Street.

Make the most of your time in Annapolis Valley - pair Windsor Pumpkin Regatta: A Nova Scotia Original (1999-2019) with our Annapolis Valley Self-Drive, Family Travel Guide, and Good Cheer Trail & Wine Country guide. They're each packed with itinerary ideas, local tips, and everything you need to extend your stay.