Cape Breton Island 
If you’re looking for a fall trip with classic scenery and something a little unexpected, Nova Scotia has a fun October option.
Credit: Nova Scotia Giant Pumpkin Festival & Regatta
You can plan your visit around two pumpkin regattas, starting with Windsor on October 4 and continuing in Shelburne (Nova Scotia Giant Pumpkin Festival & Regatta) on October 9 and 10.
Between giant gourds, waterfront races, live entertainment and family activities, the events give you a distinctly local way to experience the season. Better still, each town offers a different take on the same wonderfully quirky tradition.
Windsor brings its historic pumpkin boat race back to Lake Pisiquid on October 4, 2026, while Shelburne follows with its Giant Pumpkin Festival & Regatta on October 9 and 10. Both put giant gourds on the water, but each has its own schedule, race format and way for you to get involved directly.
What can you expect at the Regattas?
Shelburne spreads the fun across two days with a weigh-in, children’s activities, a market, timber shows and its harbour race.
If you want to paddle rather than watch, both events have ways to participate, including options aimed at newcomers and returning racers alike.
Windsor Pumpkin Regatta
Credit: Windsor Pumpkin Regatta & Build Your Own Boat Race
Windsor’s regatta began in 1999, founded by Danny Dill, son of four-time world champion pumpkin grower Howard Dill. Organizers describe it as the world’s first organized pumpkin boat race. The event later drew more than 10,000 spectators before racing paused after 2019. It returns to Lake Pisiquid on October 4.
Festival Day:
The parade is expected around 10 a.m., with racing at about 11 a.m. or noon. You can see people-powered pumpkins, motorized entries and a new Creative Entry division, where boats need not be entirely made from pumpkins. The Great Howard Dill Giant Pumpkin Weigh-Off is October 3.
How can you participate in Windsor?
To race, you need a pumpkin boat, paddle and life jacket. Organizers are helping connect paddlers with growers who may have giant pumpkins or squash. You can also enter the Build Your Own PVC category or join the Parade of Pumpkin Paddlers.
Windsor Pumpkin Regatta & Build Your Own Boat Race
Nova Scotia Giant Pumpkin Festival & Regatta
Shelburne’s festival runs October 9 and 10 along the town’s Historic Waterfront, and this year the schedule starts on Friday evening.
At 5 p.m. on Friday, October 9, you can take part in the Great Pumpkin Dash 2K/5K Fun Run, starting at the bottom of Anne Street. You can choose either the 2K or 5K route. The event is limited to 100 participants, and registration is required.
Then, at around 5:30 p.m., the Dancing Witches will appear along the Shelburne waterfront. Food vendors will also be open, and you can stay for live music at the Guild Hall later in the evening.
Saturday begins with the Giant Pumpkin Weigh-In at 10 a.m., with prizes of $1,000 for first place, $500 for second and $250 for third. You can also check out pumpkin carving for kids, bouncy houses, face painting, balloon animals, the Shelburne Guild Hall Market with more than 35 vendors, and Scotts Timber Show.
Another returning activity is the Pumpkin Derby at 1:30 p.m. on Anne Street. If you want to join, decorate a pumpkin without carving it or placing anything inside. Your pumpkin must fit inside a 12-inch by 12-inch box. Organizers provide the wheeled racing box, so you only need to bring your decorated pumpkin and see how it rolls.
The day then leads into the Nova Scotia Giant Pumpkin Regatta at 4 p.m.
Pumpkin Regatta
The Nova Scotia Giant Pumpkin Regatta starts at 4 p.m. on Saturday, October 10 along Shelburne’s historic waterfront.
Paddlers will race decorated, hollowed-out giant pumpkins through Shelburne Harbour. The Returning Rowers Race goes first, followed by the Amateurs Race.
The Returning Rowers category is for people who have paddled a giant pumpkin before, while the Amateurs Race is designed for first-time paddlers.
How can you compete in Shelburne?
You do not simply sign up and show up. Organizers are asking prospective paddlers to submit a video explaining or showing why they would be a good fit for this year’s regatta.
You can send your video through the Nova Scotia Giant Pumpkin Festival & Regatta Facebook page or by email to robin.smith@municipalityofshelburne.ca.
The deadline to submit is Wednesday, September 23.
Nova Scotia Giant Pumpkin Festival & Regatta
Extend Your Nova Scotia Fall Getaway
You can easily turn the pumpkin regattas into a longer Nova Scotia fall getaway. Pair them with a drive to Cape Breton for autumn colours, take in a Celtic festival on the island, or stop in Kentville to see the Pumpkin People displays.
If scenic views are more your style, add a few hikes to lookout points where the changing leaves do most of the work.
With so much happening across the province, the pumpkin races can be just one memorable stop on your fall route.
