EVENTS
Orillia & Lake Country is your four season destination, located 90 minutes north of Toronto. Boasting some of the best resorts, venues and attractions in Ontario such as Horseshoe Valley Resort, Casino Rama Resort, Burl’s Creek Events Grounds, Mount St. Louis Moonstone or Hardwood Ski & Bike to mention a few! The area offers many different options for accommodations such as several B&B’s, Hotels and accommodation resorts making it perfect for your over night stay! With many events happening in the area we are your go to destination for young and old located in Orillia, Oro-Medonte, Rama, Ramara, Severn and area's four season playground in Simcoe County.
Events for September 5, 2026
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All Day
Orillia Pirate Party
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 […]
Find out more »10:00 am
Pirate Day at the Leacock Museum
Arrrr! The Port of Orillia's Pirate Party is upon us and this year, Old Brewery Bay is under threat of attack! The "Pirates of the Orillian Sea" have set their eyes on the Leacock Museum and are headed our way! We are asking for the help of the community to work on boat-building crafts and […]
Find out more »Shades of Autumn Market
COME JOIN US! Shades of Autumn Market on Saturday September 5th at ODAS Park in Orillia. Shop with our incredible vendors showcasing a variety of products and services you won't be able to pass up! This is an INDOOR event and we are located in the event building once you enter the first set of […]
Find out more »Downtown Orillia Pirate Party
Set sail for family-friendly adventure at the Orillia Pirate Party in Downtown Orillia! Dress in your best buccaneer attire and join the community for a full day of high-seas excitement across the downtown core. The Ship Stage features non-stop entertainment, including children's entertainment with Dr. Bonkers, a Pet Costume Contest l, clown performances and juggling […]
Find out more »12:30 pm
Summer Music Showcase Brewery Bay
Time & Location Sep 05, 2026, 12:30 p.m. – 5:00 p.m. Higher Ground (Brewery Bay 2nd Floor), 162 Mississaga St E, Orillia, ON L3V 1V9, Canada Abby Dias - 12:30 - 2:30pm Todd & Robyn - 3:00 - 5:00pm About the event Live music on the patio? Sign us up! We have two incredible artists […]
Find out more »5:00 pm
Live Music on the Patio at Quayle’s Brewery
Listen live, local music on the patio, all weekend long! Pairs perfectly with craft beer and great food. Fun for the whole family! Thursday, September 3, 5-8pm - Sydney Riley Friday, September 4, 5-8pm - Jojo Saturday, September 5, 5-8pm - Andrew Walker Sunday, September 6, 4-7pm - Jackie Wright
Find out more »6:00 pm
Live Entertainment – Rawley Resort
Friday, Saturday & Sunday 6:00 PM – 9:00 PM Rawley Resort, Spa & Marina, 2900 Kellys Rd, Severn, ON L0K 1S0, Canada
Find out more »The Final Port of Call: Pirate After Party
After a day of treasure hunts, costume contests, live entertainment, and family fun in Downtown Orillia, head over to Brewery Bay for the Official Downtown Pirate Party After-Parrrrty. Time & Location Sep 05, 2026, 6:00 p.m. – 9:00 p.m. Higher Ground (Brewery Bay 2nd Floor), 162 Mississaga St E, Orillia, ON L3V 1V9, Canada About […]
Find out more »8:00 pm
Live Music at The Crazy Horse
June 6 – Matthew Reichenbacher June 13 – Stephan Bernard – Duo June 20 – Shawn Steinhart June 27 – Genevieve Cyr – Duo July 4 – Drew Brown July 11 – Shawn Steinhart – Duo July 18 – Andrew Walker July 25 – Karla Crawford – Duo August 1 – George Antsey August 8 […]
Find out more »9:00 pm
Live Music at the Hog & Penny
Enjoy live music at Orillia's finest pub Fridays and Saturdays from 9-11 pm. September 4 - Scott Olgard September 5 - James Gray September 11 - Dav Dickenson September 12 - No Great Mischief September 18 - Jakob Pearce & Dave Hewitt September 19 - The Kempencelts September 26 - No Great Mischief
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