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Pirate Party pillaging its way back to Port of Orillia

Event featuring re-enactors, music, scavenger hunt, pirate village, kid-friendly entertainment and more taking place Labour Day weekend
2019-09-01 Port of Orillia Pirate Party 4
The Port of Orillia Pirate Party returns on Labour Day weekend. | Nathan Taylor/OrilliaMatters file photo

The Port of Orillia Pirate Party is one week away.

This Labour Day weekend, there will be plenty of family-friendly fun at the downtown waterfront as pirates descend on the port. Entertainment and activities include live music, a scavenger hunt, life-sized “pirate ships” crewed by historical re-enactors, a “pirate village,” and a beer garden.

This will be the third instalment of the annual event, which started in 2018 but had to be put on hold for two years due to the pandemic. This year’s event builds on the popularity of the earlier ones with the addition of a pirate village and kid-friendly entertainment.

As with previous years, “landlubbers” are invited to dress like pirates for the weekend and take part in the fun.

The event is free of charge and open to the general public.

Pirate ships, crewed by historical re-enactors, will begin arriving at the port as early as Thursday evening. The re-enactors will be assembling a pirate encampment in Centennial Park, which will feature historical displays and demonstrations including a blacksmith throughout Friday, Saturday and Sunday.

Starting Friday, scavenger hunt maps will be available at the Port of Orillia and Orillia Public Library. The scavenger hunt is a free activity that sends participants through the downtown to various businesses to collect stamps and learn a piece of pirate trivia at each location. When all the stamps have been collected, participants can return their map to the Port of Orillia to be entered in a draw.

On Friday night, there will be live music at the waterfront gazebo near the Port of Orillia building.

Saturday is the busiest day of the Pirate Party, featuring a vendor market, the Rotary Beer Garden, and pirate “attacks” on both the Leacock Museum and the Port of Orillia.

Peggy Hill Team has partnered with the Sharing Place to offer games for kids near the vendor area. The games are free, but donations to the Sharing Place are welcome.

The “Walk the Plank” event, where local politicians take a plunge off the port docks to benefit the Rotary club, happens Saturday at 2 p.m.

On Sunday, the action wraps up with the final day of the scavenger hunt and musical entertainment by headliner act The Orangmen.

A full schedule of events is available at