The Pirates Are Coming to Downtown Orillia!
On Saturday September 5th from 10am – 4pm head Downtown Orillia for a day packed with pirate-themed fun! The Downtown Orillia Pirate Party is a free, family-friendly street festival where Mississaga Street will transform into a lively celebration of all things pirate.
Mississaga Street will be closed to traffic, creating an interactive playground where families can explore Downtown Orillia in a whole new way. It’s the perfect opportunity to slow down and explore the vibrant businesses that Downtown Orillia has to offer. Visitors can take part in a treasure hunt, browse local shops and vendors, enjoy food, meet roaming pirate performers and discover activities happening throughout the street. There will also be children’s activities, live entertainment, face painting, balloon art and more.
Costumes are encouraged and don’t forget to dress up your four-legged friends for the Pet Costume Contest! And make sure you snap a picture of your own pirate attire and post it on social media using #DowntownPirateParty2026 for your chance to win a $50 or $100 prize.
Downtown Pirate Party Schedule
10:00 am – Event opens
11:00 am – Pet Costume Contest
11:00 am –3:00 pm – Face Painting & Balloon Art
11:00 am –2:00 pm – Roaming Pirate Entertainment
11:30 am –1:30 pm – Interactive Animal Experience
Throughout the day – Treasure Hunt, Kids’ Activities, Shopping, Food Vendors, Live Entertainment & Community Activities
4:00 pm – Event closes
Schedule is subject to change.
The Party Continues Throughout Orillia!
The Downtown Pirate Party started as a complement to the Port of Orillia Pirate Party, a popular weekend long event that has been running for nearly a decade. From September 4th – 6th head to the Port to see life-sized ‘pirate’ ships, historical reenactments, fencing, tactical and artillery demonstrations, live music and more!
This year, swashbuckling good fun will also be taking place at The Leacock Museum! On Saturday from 10am – 3pm guests of all ages are invited to drop by the museum gift shop to pick up supplies for boat-building crafts and participate in a museum-wide treasure hunt available all day long. The main highlight comes between 10:30am and 11:00am, when the “Pirates of the Orillian Sea” launch a full-on attack on Old Brewery Bay. Be sure to head down to the waterfront or the boathouse dock for the absolute best view of the pirate ships and live cannon fire!
The Orillia Farmers Market is also getting in on the action. In addition to their regular market Saturday from 9am – 1pm at the Library, they will have vendors set up along Mississaga Street from 10am – 4pm selling locally made goods.
Keep the party going into the evening at Brewery Bay! From 6 – 9pm enjoy live music, cold drinks and great food at The Official Pirate Party After Party.
Why not make a weekend out of it? Check out the area accommodations here.
