09/10/2026
I just wanted to share something that I think makes the entire first weekend of October even more exciting — there is actually an entire weekend of pumpkin-filled fun happening right here in Windsor!
The fun kicks off Friday night, October 2nd, with the Hants Harvest & Pumpkin Jamboree Witches Walk and Night Market, along with vendors, entertainment, food, and more.
Then on Saturday, October 3rd, the pumpkin fun continues at Howard Dill Enterprises, 400 College Road, Windsor, where there will be the Giant Pumpkin Weigh-Off! Some of these incredible giant pumpkins will eventually be used in the Pumpkin Regatta on Sunday.
And, of course, Saturday is also the Hants Harvest & Pumpkin Jamboree, with our full day of activities, vendors, live entertainment, family fun, contests, food, the Pumpkin Derby, eating contests, and so much more!
Then, to finish off the weekend, Sunday afternoon, October 4th, is the Pumpkin Regatta!
The Windsor Pumpkin Regatta takes place on Lake Pisiquid at the Windsor Waterfront, where participants climb inside giant pumpkins that have been completely hollowed out and decorated, then race across the water. The traditional course runs across Lake Pisiquid between the Falmouth and Windsor sides. They also have vendors, live music and a fun zone!! Check them out!
It truly is one of those unique local traditions you have to see to believe!
So really, it’s not just one event — it’s a FULL PUMPKIN-FILLED WEEKEND in Windsor!
There will be something happening throughout the weekend for families, visitors, locals, pumpkin lovers, and anyone looking for a fun fall weekend out.
We would love to see people come out, enjoy everything Windsor has to offer, support local businesses and organizations, and make a whole weekend of it!
Three days. So much pumpkin fun. One amazing community.
Let’s make this a weekend to remember!