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Opera House
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.

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September 2026

Paint by the Lake

September 11 @ 6:00 pm - 7:30 pm
|Recurring Events (See all)

One event on September 11, 2026 at 6:00pm

One event on October 4, 2026 at 6:00pm

One event on October 11, 2026 at 6:00pm

Leacock Museum, 50 Museum Dr
Orillia, Ontario L3V 6K5 Canada
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Leacock Museum Boathouse Paint by the lake

You are invited to join us for an outdoor (or indoor, in the case of inclement weather) painting experience at the Leacock Museum! Participants will be guided through basic colour theory for mixing colours. Our paint instructor, M Nowick, will start with teaching some techniques for composing a landscape. A focus will be on creative expression for completing the scene. Inspiration will be taken from autumnal nature surrounding the Leacock Museum. Space is very limited for these workshops.  

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Don’t Sweat the Fall Stuff

September 11 @ 8:00 pm - 10:00 pm
Orillia Opera House – Studio Theatre, 1 West Street North
Orillia, ON, L3V 5B8 Canada
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The Old Dance Hall Players have been delighting audiences in Orillia for 10 years with its special brand of improv comedy — zany, irreverent, captivating, and loads of fun! All seats: $30.00 | General admission seating Recommended for ages 14 and up Estimated run time: 90 minutes | There will be one 20-minute intermission

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Live Music at the Hog & Penny

September 11 @ 9:00 pm - 11:00 pm
|Recurring Events (See all)

One event on September 5, 2026 at 9:00pm

One event on September 11, 2026 at 9:00pm

One event on September 12, 2026 at 9:00pm

One event on September 18, 2026 at 9:00pm

One event on September 19, 2026 at 9:00pm

One event on September 26, 2026 at 9:00pm

Hog & Penny, 9 Matchedash St N
Orillia, Ontario L3V 4T4 Canada
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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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Hop Harvest Tours at Quayle’s

September 12 - September 13
Quayle’s Brewery, 4567 Line 12 N
Coldwater, Ontario L0K 1E0 Canada
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Experience hop harvest season at Quayle’s Brewery and discover the journey of our hops from field to glass! Join us for a one hour guided tour through our hop yard and learn about our unique terroir, how hops are grown and harvested, and the important role they play in creating our farm-fresh beer. You’ll get an up-close look at the hop harvest and learn what makes growing and brewing with hops right here on our farm so special. Tour +…

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We Walk the Line: A Tribute to Johnny Cash

September 12 @ 7:30 pm - 10:30 pm
Orillia Opera House – G.L. Auditorium, 1 West Street North
Orillia, Ontario L3V 5B8 Canada
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Guest Rental Event: We Walk the Line: A Tribute to Johnny Cash   Experience We Walk The Line: A Tribute to Johnny Cash! 🎸This hit-after-hit show celebrates the music and legacy of "The Man in Black" and his fun-loving wife, June Carter.   Featuring Ward Cornforth as 1960s-era Johnny Cash, the performance covers Cash's legendary career, from his Sun Records days to the American Recordings era. Hear iconic songs like Ring of Fire, I Walk the Line, Folsom Prison Blues,…

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The Tenors

September 12 @ 8:00 pm - 11:00 pm
Chippewas of Rama First Nation, 5884 Rama Rd
Rama, Ontario L3V 6H6 Canada
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Showtime: 8pm • Doors Open: 7pm Pre-Sale: Wednesday, June 10 at 10am | Public Ticketmaster On-Sale: Friday, June 12 at 10am Tickets can be purchased at the Box Office or at Ticketmaster.ca, the only official ticket retailer for Casino Rama Resort shows. Click Here to Buy Tickets My Club Rewards members can use available comp to purchase tickets to this show by calling 705-329-3325 or visit Guest Services. The Tenors are an award-winning, multi-platinum & world class vocal group made…

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Big Beautiful Queens

September 12 @ 8:00 pm - 11:00 pm
Brewery Bay Food Co., 117 Mississaga St. E.
Orillia, Ontario L3V 1V6 Canada
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Get ready to be dazzled by a cast of FIERCE local queens who are bringing all the glam and laughs in one unforgettable drag show! Get ready for an unforgettable night at Brewery Bay Food Co! Join us on September 12 for the BIG BEAUTIFUL QUEENS drag show. It’s going to be a fabulous evening filled with glam, talent, and good vibes. Don’t miss out on the fun and excitement happening right in Orillia! The cast includes: Audrina Venti, Queenie…

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Live Music at Crazy Horse

September 12 @ 8:00 pm - 11:00 pm
|Recurring Events (See all)

An event every week that begins at 8:00pm on Saturday, repeating until December 26, 2026

The Crazy Horse, 1101 Horseshoe Valley Rd W
Barrie, ON L4M 4Y8
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You can enjoy the entertainment inside our main Crazy Horse dining room as you enjoy drinks, appetizers and dinner from 8-11pm. SEPTEMBER September 5 - Zachary Erickson September 12 - George Antsey September 19 - Kasey Kohring September 26 - Camryn Durante OCTOBER October 3 - Stephan Bernard October 10  - Drew Brown October 17 - Kasey Kohring October 24 - Zack Wojtala October 31 - Jeff Wardell NOVEMBER November 7 - Shawn & Matteo November 14 - Andrew Walker…

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Live Music at the Hog & Penny

September 12 @ 9:00 pm - 11:00 pm
|Recurring Events (See all)

One event on September 5, 2026 at 9:00pm

One event on September 11, 2026 at 9:00pm

One event on September 12, 2026 at 9:00pm

One event on September 18, 2026 at 9:00pm

One event on September 19, 2026 at 9:00pm

One event on September 26, 2026 at 9:00pm

Hog & Penny, 9 Matchedash St N
Orillia, Ontario L3V 4T4 Canada
+ Google Map

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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Autumn Tea at the Leacock Museum

September 13
|Recurring Events (See all)

One event on September 20, 2026 at 12:00am

Leacock Museum, 50 Museum Dr
Orillia, Ontario L3V 6K5 Canada
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The Leacock Museum is hosting an warm and cozy autumn-themed high tea this September! Guests are invited to enjoy a three-tiered treat selection prepared by Krew Catering with unlimited tea while seated in the decorated and historic living room, dining room, and sunroom of the Leacock Museum. Tickets to the Autumn Tea also include a self-guided tour of the museum Seatings available September 13th & 20th  at 11am & 2pm. Sign up here.

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