Three days of pirate adventures, live entertainment and family fun September 4-6, 2026
Ahoy, mateys! The Pirates of the Orillian Sea are once again preparing to storm Orillia’s downtown waterfront for a weekend of swashbuckling fun. From Friday, September 4 to Sunday, September 6, 2026, the Port of Orillia and Couchiching Beach Park will come alive with pirate battles, live music, entertainment, vendors, games, and activities for visitors of all ages.
The Port of Orillia Pirate Party, presented by the Orillia & District Chamber of Commerce, began in 2018 and has grown into a beloved local tradition and one of Orillia’s favourite summer events. Each year, the event brings the community and visitors together for a unique celebration that combines Orillia’s waterfront, local businesses, live entertainment, and a little pirate mayhem.
“The Pirate Party is just one of the many ways our member businesses give back to the community and help make Orillia such a great place to live, work and visit,” says Allan Lafontaine, Executive Director of the Orillia & District Chamber of Commerce. “With more than 500 members across our region, there are so many businesses working every day to support our community, create local experiences, and contribute to a vibrant local economy. We’re proud to bring our members together through events like the Pirate Party and invite everyone to come out and experience all that our local business community has to offer. You can discover our 500-plus member directory at www.orillia.com.”
The pirate action begins Friday evening with the Pirates’ “Pub Crawl” in Downtown Orillia. Members of the public are encouraged to put on their best pirate attire and take part in a self-guided adventure through downtown. The evening continues at the Port of Orillia with a musical performance by Mudmen at 8:00 p.m., followed by Movies in the Park at the Rotary Aqua Theatre in Couchiching Beach Park at 9:00 p.m., featuring Pirates of the Caribbean: The Curse of the Black Pearl.
Saturday will be packed with pirate activity from morning until night. The Pirate Village, featuring costumed re-enactors and historical demonstrations, will be in full swing throughout the day, while Downtown Orillia hosts its Pirate Party activities from 10:00 a.m. to 5:00 p.m. The Vendor Market at the Port of Orillia runs from 12:00 p.m. to 6:00 p.m., offering visitors a chance to browse a variety of local goods and offerings.
The day’s pirate encounters include battles “at sea” and on land. The Rotary Club of Orillia will be hosting a “Walk the Plank” challenge, raising funds for the community, at 4:00 p.m. Anyone interested in participating can learn more and sign up at https://portal.clubrunner.ca/215/calendaritem/details?calendaritemid=fd9c6eae-6f05-42a4-81ae-f50c0ccacf29&start=2026-09-05&end=2026-09-05. Later, the fun continues with Fat Tony Band performing at Port of Orillia at 8:00 p.m.
The adventure continues Sunday with another full day of activity in the Pirate Village and the Vendor Market from 10:00 a.m. to 5:00 p.m. No Great Mischief Band will provide live music from 11:00 a.m. to 3:00 p.m., and more pirate battles will take place throughout the day, and a special performance from Captain Corbin the Magical Pirate at 5:00 p.m. The weekend will come to a close with Orangeman taking the stage for at Port of Orillia at 8:00 p.m.
A full schedule of events for the Pirate Party, including performance times and additional details, is available at www.orillia.com/pirate-party/.
