On Labour Day Weekend, Pirates Invade the Port of Orillia!
Prepare to batten down the hatches — the Pirates of the Orillian Sea are setting their course for Orillia’s Downtown Waterfront! Word on the wind is they’ll make landfall just in time for Labour Day weekend, bringing a treasure chest full of swashbuckling fun, live entertainment, and high-seas adventure for the whole family.
Event Date:
August 29 - September 1, 2025
Location:
Port of Orillia - 50 Lightfoot Dr, Orillia, ON
The Orillia Pirate Party features:
• Life-sized "pirate" ships crewed by historical re-enactors
• Fencing, tactical, and artillery demonstrations
• Pirate encampment village featuring a blacksmith demonstration, costumed re-enactors, and historical props
• Live musical entertainment
• Food and vendors
• Downtown scavenger hunt
Event Schedule
Live Pirate Entertainment- Friday through Sunday at Scheduled TimesÂ
Watch as costumed re-enactors portray pirate battles, featuring historical artillery demonstrations, life-sized replica ships, and plenty of excitement! See performance schedule below:
Friday August 29
- 5:00 PM – "Pirate Crews Attack the Orillia Opera House" - pirates march up Mississaga Street to the historic Opera House at 1 West Street North.
Saturday August 30
- 10:30 AM – "Attack on Lord Leacock’s Manor" - pirates sail from Port of Orillia to the Steven Leacock Museum to carry out an "attack from sea" - spectators can view the ships leaving Port at 10:00 a.m. and the battle at the Leacock Historical Site at 50 Museum Drive at 10:30 a.m.
- 11:00 AM – "Attack on Champlain Sailing Club" - following their attack at the Leacock property, the ships carry out another seige from sea at 145 Cedar Island Rd.
- 2:00 PM – "Attack on the Port of Orillia" - sea battle at the Port of Orillia
- 3:00 PM – "Pirates vs. Lord Mayor’s Garrison" - land battle performance at Couchiching Beach Park in the field next to the beach
- 4:00 PM - "Walk the Plank" - a pirate spin on a dunk tank; watch as the Pirate King forces victims to walk the plank and splash into the waters of Lake Couchiching; raising funds for the Rotary Aqua Theatre
Sunday August 31
- 10:00 AM - "Pirates Sail to Skull Island to Bury Treasures"Â -Â watch as the ships set sail from Port of Orillia
- 2:00 PM -Pirate ships return to Port of Orillia
- 2:30 PM - "Pirates vs. Lord Mayor’s Garrison" - land battle at Couchiching Beach Park in field next to the beach
- 3:30 PM - Battle at Sea at the Port of Orillia
- 4:00 PM -  Champlain Sailing Club arrives at Port of Orillia to battle pirates
Live Music
Enjoy free live musical performances all weekend at scheduled times. All performances take place at the Port of Orillia (stage will be in the small gazebo next to the Port). Bring a lawnchair!
Friday, August 29 - Connor Brothers - starting at 9 p.m. / Saturday, August 30 - Fat Tony Band - starting at 9 p.m.
Sunday, August 31 -Â Orangeman- starting at 9 p.m.
Monday, Sept. 1 - Run with Kittens Featuring Opening Performance by Orillia's Got Talent Winner Evie Johnstone - starts at 1 p.m.
"Treasure Hunt" Downtown Scavenger Hunt- All Day Friday through Sunday
Download the Explore Orillia & Lake Country App and take part in an epic hunt for pirates in Orillia's historic downtown. Instructions are in the app. All who complete the hunt will be entered in a draw to win a prize basket!
Pirate Life Boat Cruises (Additional Fees Apply) - Friday though Monday
Departs each day at 9:30 AM, 10:45 AM, 12:00 PM, 1:15 PM, 2:30 PM, 3:45 PM from Port of Orillia. Cost $35/ $10 for kids under 3. Go to https://piratelife.ca/book-now for more information & to book.
Pirate Village & Pirate Games - All Day Saturday and SundayÂ
- Visit a historical village with costumed re-enactors portraying pirates - featuring duels, cooking demos, blacksmithing, rope making, and more - in Centennial Park adjacent to Port of Orillia
- Pirate Games: Plank Run, Shark Attack, Pirate Art, Face Painting, Tug of War, Pirate Wrestling, Photo Booth (additional fees may apply for some activities)Â located in Centennial Park adjacent to Port of Orillia
Vendor Market - Saturday and Sunday
Located in Centennial/ Couchiching Beach Park
Hours of Operation: Saturday noon to 6 p.m. / Sunday 10 a.m. to 5 p.m.
"Walk the Plank" Rotary Fundraising Event - Saturday, August 30 at 4:00 p.m.
Watch as participants walk the plank and splash into the Port of Orillia waters to raise funds for Rotary Aqua Theatre refurbishments. Minimum $20 pledge to participate- pledge forms available by contacting office@orillia.com and all participants must be over 18 years of age.
Boat Judging & Awards: Best Dressed Crew, Best Decorated Ship- Saturday, August 30 at 5:00 PM at Port of Orillia Docks
Downtown Orillia Pirate Party- SATURDAY ONLY
From 10:00 a.m. to 5:00 p.m., enjoy pirate-themed family entertainment, sidewalk sales, and music along Mississaga Street in Downtown Orillia. Visit the Downtown Orillia Pirate Party Facebook page for more information and updates.
