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What’s on Where: Barrie, Orillia and Surrounding Area

On Labour Day Weekend, Pirates Invade the Port of Orillia!

March 27, 2025
| Family Events, Special Events, What's on Where: Barrie, Orillia and Surrounding Area
Pirate Party

August 29 – 31, 2025
Port of Orillia

Yo-ho! It’s time to batten down ye hatches because the “Pirates of the Orillia Sea” have their sights set on the City’s Downtown Waterfront. They are expected to make landfall just in time for the Labour Day weekend, and are bringing with them a weekend of fun and entertainment for all ages!

The Orillia Pirate Party features:

  • Life-sized “pirate” ships crewed by historical re-enactors
  • Fencing, tactical, and artillery demonstrations
  • Pirate encampment…

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Experience Canada’s Premier Country Music Event at Boots and Hearts 2025

March 27, 2025
| Festivals/Fairs, What's on Where: Barrie, Orillia and Surrounding Area
Boots and Hearts Music Festival: Canada's Largest Camping & Music Festival

August 7-10, 2025
Burl’s Creek, Line 7 and Line 9 South off of HWY 11

Get ready for an unforgettable weekend at Boots and Hearts Music Festival, Canada’s Largest Camping & Music Festival, taking place from August 7-10, 2025, at Burl’s Creek, Ontario. Known for its stellar lineup of country music’s biggest stars and rising talents, the festival promises four days of non-stop entertainment, community, and celebration. Attendees can enjoy world-class performances, interactive experiences, and a true outdoor…

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Orillia Waterfront Festival: A Weekend of Boats, Markets & Family Fun!

March 19, 2025
| What's on Where: Barrie, Orillia and Surrounding Area
Orillia Waterfront Festival

August 8 – 10, 2025
Port of Orillia

The Orillia Waterfront Festival is set to make a grand return from August 8 to 10, 2025, at the picturesque Port of Orillia. This annual celebration has become a cornerstone of the community, offering a diverse array of activities and attractions that cater to all ages.

Event Highlights

  • In-Water Boat Show: Boating enthusiasts can look forward to an impressive display of new and pre-owned vessels. Local dealers such as Pride Marine,…

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47th Orillia Scottish Festival 2025: Celebrating Scottish Heritage in Ontario

March 3, 2025
| What's on Where: Barrie, Orillia and Surrounding Area
Orillia Scottish Festival

July 18 – 20, 2025
Tudhope Park, Orillia

The Orillia Scottish Festival, a cherished annual event since 1978, is set to celebrate its 47th edition from July 18 to 20, 2025. This festival, the longest-running in Orillia, Ontario, offers a vibrant showcase of Scottish heritage and culture, drawing visitors from near and far to the picturesque Couchiching Beach Park and the Royal Canadian Legion Branch 34.

Festival Highlights:

  • Friday, July 18: The festivities commence with a lively Ceilidh at…

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