On your marks, get set, gourd!

Nestled in Nova Scotia’s Annapolis Valley is the small town of Windsor. Officially established in 1878, the town was a shipbuilding hub during the 19th and 20th centuries and is said to be the birthplace of hockey. One of the town’s more zany claims to fame, however, is the annual pumpkin regatta. 

The event was started in 1999 by Danny Dill, owner of Dill family farm and son of Howard Dill, the man responsible for growing some of the biggest pumpkins this country had ever seen. The story goes that Dill was asked by locals for ideas on how to make the town’s pumpkin weigh-ins a tad more exciting, leading Dill to invent one of the first Personal Vegetable Crafts (PVCs). Windsor residents at this first event were reportedly amazed by how well the pumpkins could float. The race became an annual event for the town, bringing in more and more attention each year. In 2018, over twenty thousand people were in attendance.

The regatta itself involves participants carving out giant pumpkins, often still grown on the Dill family farm, and racing other PVCs across an 800 metre course on the town’s Lake Pesaquid. Each pumpkin is around 600 pounds and is decorated lavishly by its sailors. It is also common for competitors to dress up in costumes, including pumpkin helmets. The event has seen up to 50 registered contestants and has featured three different race categories: motored, experimental, and paddling – paddling being the most popular.

With each race, there are always pumpkins that prove to be unseaworthy right from the start, but that is far from the case for one Leo Swinimer, six-time regatta winner. Swinimer was a long time supporter of the regatta, winning his last race at 73. Swinimer’s winning strategy included growing his own pumpkins, upside down, and reinforcing the walls of the gourd with foam. 

The 2005 regatta garnered national attention when the town was set to have a very special guest flying in: Martha Stewart. The American television personality was all set to race in the regatta as a fundraiser for the Make a Wish foundation. Unfortunately, she was delayed from entering the country due to an insider trading scandal which saw her spend time behind bars in 2004. Her criminal status caused her Visa to lapse and by the time the issue was resolved, a storm rolled in, cancelling her flight. Luckily, her 300 pound, specially-decorated pastel pumpkin did not go to waste, as one of Stewart’s producers took her place.

The event was unfortunately cancelled in 2020 and 2021, due to provincial gathering guidelines put in place for the Covid-19 pandemic. Despite this, there was hope that the regatta would return to Windsor once restrictions were lifted. These hopes were crushed in May of 2021, when an abattoir was ordered to be opened by the Department of Fisheries, causing Lake Pesaquid to be drained in order for fish to pass through. The draining caused controversy in the community, with many farmers deprived of a vital water source for their crops. Others supported the government’s decision, as a way to protect the fish populations. One thing was clear however: no water meant no regatta. Danny Dill himself told CBC in 2022, “You need three ingredients. You need water, a giant pumpkin and some crazy person to paddle it.”

In 2022, Dill supplied pumpkins for a new regatta, this time in Shelburne, a community on the South shore of Nova Scotia, almost 200km away from Windsor. While some were glad the tradition of the regatta was continuing, many were upset about the loss of the event from the Windsor community. In 2023, Lake Pesaquid was refilled to act as a water source to battle the ongoing wildfires in the province. Many were hopeful that this would also signal the return of the regatta to Windsor, but this has not been the case. 

In 2023, coordinators of the event cited the lack of preparation time as the reason the event was not returning. However, in 2024, the event again took place in Shelburne on October 14, with no assurance from event coordinators or town officials if there are plans for the event to return to its roots in Windsor. Community members have attempted to get new events off the ground, such as a pumpkin-mobile derby: a dryer, on-land version of the classic race. While social media pages for the derby have gained traction, the event has unfortunately failed to get the go-ahead from the town in the past two years. With Nova Scotia Premier Tim Houston promising that he will “not allow that lake to drain” anytime soon, there remains hope that someday those ginormous gourds will once again return to Windsor.