This Friday marks the return of the Port of Orillia Pirate Party, bringing three days of free entertainment, live music, pirate battles and family fun to the waterfront. What began in 2018 as an idea to extend Orillia’s summer tourism season has grown into one of the Port’s signature weekends for boaters, residents, visitors and Chamber members.
“When we started this in 2018, our goal was really quite simple—we wanted to extend summer,” said Allan Lafontaine, Executive Director of the Orillia & District Chamber of Commerce. “At the time, we were averaging only about 30% occupancy at the Port over Labour Day weekend. I was new at the Chamber and fortunate to sit down with Bob Brown from Thor Motors, John Ward from Country Produce and John Tselikis from Theo’s. I told them about this crazy idea to bring pirates to the Port, and they immediately stepped up to help get the fundraising started.”
Lafontaine credits the community for turning the idea into reality. Then-Chamber President Peggy Foley and the Chamber Executive gave the project the green light, while Bill Ecklund of Home Hardware agreed to build the plank for the inaugural Walk the Plank fundraiser. Businesses and community organizations quickly joined the effort as sponsors and supporters.
“This is one of the things that makes Orillia special,” said Lafontaine. “The community simply came together.”
From an Idea to a Labour Day Tradition
Another critical piece of the event came when Lafontaine met Tom Hurlbut of the Simcoe Squadron at a pirate event in Penetanguishene.
“Meeting Tom was really the spark that made the magic happen,” said Lafontaine. “Without Tom Hurlbut, this event simply wouldn’t have been as special. He helped turn an event into an experience.” Hurlbut an Orillia resident, has been doing naval re-enactments for years and this has been an opportunity to bring so many from across Canada to participate in the weekend event. Even though the Pirates we portray are a made up Johnny Depp version, there are many parts of the late 1600’s golden age of the Caribbean Pirates that ring true to the uniforms, boats and cannons used in the weekend fun.
The first Pirate Party in 2018 helped increase Port occupancy to approximately 65%, with boaters and visitors beginning to embrace the pirate theme. Being a municipal election year, the Walk the Plank quickly became a centrepiece of the weekend, with politicians and community personalities taking the plunge while raising money for the Rotary Aqua Theatre through the Rotary Club of Orillia.
In 2019, MD Marine became a major sponsor of the Chamber’s summer events, providing additional resources to expand the Pirate Party. That year, the Port sold out its slips for the weekend and Couchiching Beach Park filled with boaters, residents and visitors dressed as pirates—with even four-legged pirates joining the fun.
“We knew then that we had something,” Lafontaine said. “By 2021, we had waiting lists for slips and Pirate Party had become one of those weekends boaters planned their summer around, much like Christmas in June.”
Three Days of Free Entertainment
The 2026 celebration kicks off Friday evening with The Mudmen performing at 8 p.m. at the Port of Orillia, followed by Pirates of the Caribbean at 9 p.m. at the Rotary Aqua Theatre.
Saturday features pirate entertainment throughout the day, including epic land and sea battles. At 4 p.m., 14 registered participants will Walk the Plank at the Rotary Aqua Theatre in support of Rotary’s continued involvement with the historic facility.
The Rotary Club of Orillia built the Aqua Theatre in 1958 and subsequently turned it over to the City of Orillia. The Club has remained passionate about its future, including funding accessibility planning and supporting musical programming at the facility.
Saturday evening continues with The Fat Tony Band at 8 p.m.
Pirate activity continues throughout Sunday, including the final land battle in Couchiching Beach Park and another battle on the water, before The Orangeman takes the stage at 8 p.m. to close out the weekend.
A Community Effort
MD Marine continues to play a major role in supporting the event, while Peacock Tariff Consulting is providing music support this year.
The Chamber is also grateful for the support of the Ministry of Tourism, Culture and Gaming through the Experience Ontario Program, as well as the City of Orillia through its Special Events Grant. This support helps make it possible to deliver the Pirate Party and continue bringing free entertainment and activities to the community each Labour Day weekend.
The Chamber also recognizes that the Pirate Party would not be possible without the ongoing support of its entire membership.
“Every Chamber member plays a role in making our festivals and events possible,” said Lafontaine. “Through their membership, sponsorships and participation, our businesses invest in activities that bring people into our community. We encourage everyone attending Pirate Party to visit orillia.com, discover a Chamber member and support the businesses that support our community.”
Downtown Orillia is also participating in the celebration, with the downtown street closure returning for a second year and DOMB taking over the downtown treasure hunt for free family fun all day Saturday.
All scheduled music and entertainment at Pirate Party is free to the public. This year, Pirate Party buttons will also be available by donation, with proceeds helping the event continue to grow.
The Chamber looks at Labour Day weekend as an opportunity for our businesses and organizations to give something back to the people who work, live and visit here,” said Lafontaine. “It’s our opportunity to say thank you to the community for being the sunshine in the Sunshine City. It also gives hotels, shops and restaurants one more weekend to earn income before the fall and winter sets in. ”
The weekend includes considerably more music, pirate entertainment, battles and activities than can be listed here.
For the complete 2026 Port of Orillia Pirate Party schedule, visit:
orillia.com/pirate-party/
