You can race giant pumpkins across a Canadian harbour this October

For those residing in (or planning to visit) the Maritimes, there’s a fun fall tradition coming up that you’ll want to mark your calendars for. The fifth annual Nova Scotia Giant Pumpkin Festival and Regatta is set to bring all the spooky vibes to Shelburne’s historic waterfront over Thanksgiving weekend, and 2026 is a big year for the festivities.

Giant pumpkins galore

Among the most popular events are the giant pumpkin weigh-in and regatta on Shelburne Harbour, where people use some of the largest pumpkins you’ve ever seen to paddle their way to first place.

The fun kicks off on Friday, Oct. 9, with the Shelburne waterfront transforming into a bewitching display of dancing witches. Starting around 5:30 p.m., there will be all kinds of hocus pocus vibes along the waterfront, complete with food vendors and live music at the Guild Hall.

New this year is the Great Pumpkin Dash, a fun run (a 2K and a 5K) at 5 p.m. on Friday that starts at the bottom of Anne Street.

If you’ve always wanted to participate in a run like this, now is your chance to have fun with it. Don your witch hat or a fake nose and make a dash for the finish line.

Note that the run is limited to 100 participants, so advance registration is required.

On Saturday, the pumpkin weigh-in will commence along the waterfront at 10 a.m., with awards going to the heaviest field pumpkin ($100), tallest sunflower ($100), and the heaviest squash, which must be over 400 lbs ($250).

The giant pumpkin regatta will feature two races: The Returning Rowers Race for those who are seasoned pumpkin paddlers, and the Amateurs Race, perfect for beginners.

So if floating away in a decorated, hallowed-out pumpkin sounds like your cup of tea, the latter race is the perfect, low-stakes way to enjoy just that.

Other festive activities to look forward to over Thanksgiving weekend include classic pumpkin carving, face painting, bouncy houses, a timber show, and the Shelburne Guild Hall Market.

It’s time to plan a magical fall road trip to Nova Scotia!

When: Friday, Oct. 9 and Saturday, Oct. 10, 2026
Time: Various times throughout Thanksgiving weekend
Where: Various locations along Dock Street, Shelburne, N.S.
Cost: Free admission

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