Windsor Pumpkin Regatta

Origins and history

The Windsor Pumpkin Regatta was founded in 1999 by Danny Dill, continuing a local legacy tied to giant pumpkin cultivation pioneered by his father, Howard Dill. The event was conceived as a whimsical way to demonstrate the buoyancy and size of the Atlantic Giant pumpkin, a variety developed in the region. While not the first instance of pumpkin paddling, with Wayne Hackney of New Hampshire credited with the first voyage in 1996, the Windsor event quickly became a signature autumn tradition. The regatta ran annually from its inception until 2019, building a dedicated following and establishing itself as a key part of community life in Windsor and West Hants.

The event faced significant challenges starting in 2020 when it was cancelled due to public health restrictions during the COVID-19 pandemic. A more permanent obstacle arose in 2022 when a ministerial order from Fisheries and Oceans Canada altered the operation of tidal gates at the Avon River causeway. This change in water management led to the draining of the manmade Lake Pisiquid, leaving insufficient depth to safely host the races, and the event was cancelled indefinitely. With the event on hold, the nearby community of Shelburne County began its own pumpkin regatta in 2022 to fill the void for enthusiasts.

The Windsor Pumpkin Regatta tradition was revived in 2025 due to the efforts of local residents like Roland Newcomb and Theresa Weatherbee. An impromptu race with four competitors was held over the Thanksgiving weekend that year. Theresa Weatherbee won this race, which demonstrated the event's viability. This success led to the formation of the Windsor Pumpkin Regatta and Build Your Own Boat Race Society to plan a 2026 festival. The event's return was aided by a 2023 provincial order that refilled Lake Pisiquid for wildfire control.

Event format and competition

The regatta features a half-mile (800-metre) course on Lake Pisiquid, with competitors using giant pumpkins as their sole means of flotation. The pumpkins, typically weighing between 500 and 700 pounds, are hollowed out and often brightly decorated before being launched. Over the years, the event has included several competition classes to accommodate different styles of propulsion and creativity. The three main historical classes are the paddling class, the motor class, and the experimental class, though not all classes attract entries every year.

The paddling class, where participants use hand paddles to propel their gourds, is the best known and has traditionally attracted the most competitors. The motor class allows for small outboard motors, while the experimental class has been a space for more inventive, hybrid watercraft. For the 2026 revival, organizers have introduced a new creative entry division to encourage broader participation, welcoming entries that incorporate pumpkins for decoration or flotation but are not required to be made entirely from a single gourd. The competition has seen notable dominance by certain paddlers, most famously Leo Swinimer of New Ross, Nova Scotia, who won six of the first ten regattas, including a victory at the age of 73.

The 2008 Windsor Pumpkin Regatta was a high point, attracting about 10,000 spectators and 60 entries. The event's founder was Danny Dill, son of Atlantic Giant pumpkin breeder Howard Dill. The race features three classes which are motor, experimental, and paddling. The 2026 event is scheduled for the day after the Great Howard Dill Pumpkin Classic Weigh-off.

• 1999: First Windsor Pumpkin Regatta is held, founded by Danny Dill.
• 2005: Martha Stewart plans to participate, generating significant publicity.
• 2008: Event peaks with about 10,000 spectators and 60 entries.
• 2019: Last annual event before a multi-year hiatus.
• 2022: Shelburne County launches its own pumpkin regatta.
• 2025: Impromptu revival race held with four competitors.
• 2026: Full festival scheduled for October 4 with new creative entry division.

Notable participants and public profile

The Windsor Pumpkin Regatta has attracted attention beyond its local community through the participation of several well-known figures. In 2005, American media personality Martha Stewart planned to compete, generating significant publicity for the event, though she was unable to attend due to delayed entry permission and weather. More consistently, the event has enjoyed support from local political figure Scott Brison, the former Member of Parliament for Kings, Hants, who has participated in multiple races. The regatta's unique concept has inspired similar events elsewhere in North America, including one at the University of Wisconsin-Madison starting in 2005 and another on Lake Champlain in Vermont.

Public interest in the event remains strong, as evidenced by the community-led effort to revive it in 2025 after the lake was refilled. The organizing society reported overwhelmingly positive feedback when announcing the 2026 return, promoting it as a full day of fall festivities with a morning parade open to various community groups. This broader festival atmosphere helps cement its status as a must-see regional attraction, drawing visitors and supporting local businesses. Other notable individuals and groups associated with the regatta include:

• Howard Dill: The Atlantic Giant pumpkin breeder whose work made the event possible.
• Leo Swinimer: The most successful paddler, with six wins in the first ten years.
• Roland (Rollie) Newcomb: The local senior whose wish inspired the 2025 revival.
• Shannon Murphy: Chairperson of the organizing society for the 2026 event.
• The Shelburne County Festival: A separate Nova Scotia regatta begun in 2022.
• 2025 Competitors: Included Leah and Stacey Robinson-Stocco and Jacques Gosselin.

The 2025 revival and 2026 plans

The impromptu 2025 race fulfilled local resident Roland Newcomb's wish to see the tradition revived. Participants included Leah Robinson-Stocco and Stacey Robinson-Stocco in a Blue Jays themed pumpkin. Jacques Gosselin from Montreal raced in a modified watercraft, and Theresa Weatherbee won the race. This event proved the lake could host the regatta again and built community support. It led to the formation of the Windsor Pumpkin Regatta and Build Your Own Boat Race Society, chaired by Shannon Murphy.

Planning for the 2026 Windsor Pumpkin Regatta is now underway, with the society announcing the event will be held on October 4, 2026. The day will start with a parade at 10 a.m. open to more than just pumpkin paddlers, followed by the regatta races at approximately 11 a.m. or noon. Organizers have secured commitments for a dozen giant pumpkins from local growers, though they acknowledge the challenge of pumpkin scarcity and reliance on favourable growing conditions. They actively encourage creative entries for the new build-your-own-boat division to ensure a strong field of competitors and welcome new committee members to help organize.

The event's return was possible because a 2023 provincial emergency order refilled Lake Pisiquid for wildfire control. The 2026 regatta is planned as a community celebration with Roland Newcomb as a special dignitary. The event will have different divisions including people powered and motorized pumpkins. Organizers have secured 12 giant pumpkins for the race, with an ideal weight between 500 and 700 pounds.

• Date: October 4, 2026.
• Parade Start: 10 a.m., open to community floats.
• Race Start: Scheduled for 11 a.m. or noon.
• Pumpkins Secured: 12 giant pumpkins committed for the race.
• New Division: Creative build-your-own-boat entry.
• Ideal Pumpkin Weight: Between 500 and 700 pounds.
• Registration: All vegetable watercraft must be reserved in advance.

Logistics and community role

Organizing the Windsor Pumpkin Regatta involves considerable logistical planning, from securing giant pumpkins to managing race day activities on the waterfront. The giant Atlantic pumpkins required for the race are the product of months of careful cultivation by dedicated growers, making their availability subject to weather and growing conditions. For the 2026 event, organizers are accepting advance reservations for all vegetable watercraft to ensure proper planning and coordination with local authorities for safety, traffic management, and the use of public spaces along the Lake Pisiquid shoreline. The regatta has historically played a significant economic and social role for the town of Windsor and West Hants, drawing visitors from across the province and beyond.

At its peak, the event attracted upwards of 15,000 people to the waterfront, providing a boost to local businesses and highlighting the community's innovative spirit. The festival atmosphere, combining the race with a parade and other festivities, makes it a key family-friendly attraction during the Nova Scotia autumn and a point of local pride. The organizing society actively seeks new members and ideas to help ensure the event's long-term sustainability and success, emphasizing community ownership and creativity. This grassroots model was fundamental to the 2025 revival and continues to shape the planning for 2026, aiming to re establish the Windsor Pumpkin Regatta as a permanent and cherished annual tradition.

Questions about Windsor Pumpkin Regatta

When and where is the Windsor Pumpkin Regatta held?

The Windsor Pumpkin Regatta is held on Lake Pisiquid in Windsor, Nova Scotia. The revived event is scheduled for October 4, 2026. Historically, the races have always taken place in October, aligning with the pumpkin harvest and other autumn festivals in the region. The course stretches for a half mile, or 800 metres, across the lake.

What kind of pumpkins are used in the race?

Competitors race in giant Atlantic pumpkins, the same variety bred by Windsor's own Howard Dill. The ideal pumpkin for the regatta weighs between 500 and 700 pounds. These massive gourds are hollowed out to create a buoyant vessel capable of supporting a person. The pumpkins are often brightly painted and decorated by their pilots before the race.

Why was the regatta cancelled after 2019?

The event was cancelled in 2020 and 2021 due to the COVID-19 pandemic. In 2022, it was cancelled indefinitely after a federal ministerial order changed how tidal gates at the Avon River causeway were operated. This change drained Lake Pisiquid, leaving insufficient water depth to safely hold the races. The lake was later refilled in 2023 under a provincial order for wildfire control.

Can anyone participate in the pumpkin race?

Yes, the regatta encourages community participation. Organizers secure giant pumpkins for competitors and also welcome creative entries in a new build-your-own-boat division, where vessels can be decorated with or floated by pumpkins. All vegetable watercraft must be reserved in advance with the organizing society. The event includes different divisions for paddling, motorized pumpkins, and creative entries.

Who founded the Windsor Pumpkin Regatta?

The Windsor Pumpkin Regatta was founded in 1999 by Danny Dill. He is the son of Howard Dill, the renowned breeder of the Atlantic Giant pumpkin variety. The event was established as an annual pumpkin regatta held on Lake Pesaquid in Windsor, Nova Scotia. It features races where participants use hollowed out giant pumpkins as their sole means of flotation. The regatta quickly grew in popularity, attracting thousands of spectators and numerous competitors over the years.

How was the Windsor Pumpkin Regatta revived?

The Windsor Pumpkin Regatta was revived due to the efforts of local residents, led by senior citizen Roland Newcomb and Theresa Weatherbee. In 2025, they organized an impromptu race over the Thanksgiving weekend on Lake Pisiquid, which featured four competitors. This successful demonstration spurred the formation of the Windsor Pumpkin Regatta and Build Your Own Boat Race Society to plan a full festival for 2026. The revival was made possible because a provincial emergency order to refill the lake for wildfire concerns restored the necessary water levels, which had previously been too low for the event after 2019.

Sources and further reading

• Windsor Pumpkin Regatta (Wikipedia)
• A Windsor tradition returns: Popular pumpkin regatta being ... (saltwire.com)

Checked by the Garbutt Disposal desk. Last updated 2026-10-24.