Windsor Pumpkin Regatta & Build Your Own Boat Race

Head to the Windsor waterfront on Sunday, October 4, 2026 for one of the most unusual races in the world: paddlers carving giant pumpkins into boats and racing them across Lake Pisiquid. Festivities open with a parade through downtown Windsor at 10 a.m. — open to everyone, not just pumpkin paddlers — before the regatta hits the water around 11 a.m. or noon. The event is the finale of the Hants Harvest & Pumpkin Jamboree weekend and a signature stop on any Annapolis Valley fall trip.

The regatta runs several race divisions: people-powered pumpkins, motorized pumpkins, and — new for 2026 — a Creative Entry division featuring pumpkin-themed builds that don't need to be made entirely from pumpkins. Windsor claims the world's first pumpkin regatta, dating to 1999, when local growers first climbed inside giant gourds and paddled for the far shore; the town's agricultural roots show everywhere, from the parade floats to the growers' weigh-ins. It's free to watch and made for families.

Pair the regatta with the rest of Windsor's fall calendar: the Windsor Hants County Exhibition (Sept 18-27) kicks off the season, and the Kentville Pumpkin People Festival runs October 3-25 just 20 minutes down the Valley. Base yourself in Wolfville — Blomidon Inn or the other Main Street inns are 25 minutes away — and make a foliage weekend of it.

Make the most of your time in Annapolis Valley - pair Windsor Pumpkin Regatta & Build Your Own Boat Race 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.