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:
September 4-6, 2026
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
Schedule of Events
Friday, September 4
- 7:00 PM – Pirates’ “Pub Crawl” in Downtown Orillia – Public welcome to dress up and participate (Self Guided).
- 8:00 PM – Music at Port: Mudmen
- 9:00PM – Movies in the Park - Pirates of the Caribbean: The Curse of the Black Pearl
Saturday, September 5
Ongoing All Day
- Animation of Pirate Village: pirates, duels, games, blacksmithing, rope making, and more
Special Events
- 10:00 AM – 5:00 PM – Downtown Orillia Pirate Party
- 12:00 PM – 6:00 PM – Vendor Market
- 11:00 AM – Attack on Lord Leacock’s Manor
- 11:00AM - Wild Animal Kingdom Show
- 12:00 PM & 3:00 PM – Pirate Queen’s Challenges – Kids Cannon Demo
- 1:00 PM – Attack on the Port of Orillia
- 2:00 PM – Land Battle: Pirates vs. Lord Mayor’s Garrison (Couchiching Beach Park)
- 4:00 PM – Walk the Plank
- 6:00 PM – Boat Judging & Awards: Best Dressed Crew, Best Decorated Ship
- 8:00 PM – Music at Port: Fat Tony Band
Sunday, September 6
Ongoing All Day
- Animation of Pirate Village: pirates, duels, games, blacksmithing, rope making, and more
Special Events
- 10:00 AM – 5:00 PM – Vendor Market
- 11:00 AM – 3:00PM – No Great Mischief Band
- 11:00 AM – Attack on Champlain Sailing Club
- 11:00AM - Wild Animal Kingdom Show
- 12:00 PM & 3:00 PM – Pirate Queen’s Challenges – Kids Cannon Demo
- 1:00 PM – Land Battle: Pirates vs. Lord Mayor’s Garrison (Couchiching Beach Park)
- 4:00 PM – Battle at Sea
- 5:00 PM - Captain Corbin The Magical Pirate – Magic Show
- 8:00 PM – Music at Port: Orangeman
