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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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October 2025

The Oscar Peterson Centennial Quartet

October 18, 2025 @ 7:30 pm - 9:30 pm
Orillia Opera House – G.L. Auditorium, 1 West Street North
Orillia, Ontario L3V 5B8 Canada
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The Oscar Peterson Centennial Quartet celebrates Oscar Peterson's life and music in a unique live concert presentation featuring music from Peterson's seven-decade career, with multimedia presentations and conversation. The core band features acclaimed Canadian musicians, JUNO Award winners Robi Botos (piano), Mike Downes (bass), Jim Doxas (drums) and world-renowned musician and ten-year veteran of the Oscar Peterson Quartet, Ulf Wakenius, (guitar). Peterson's daughter, Celine Peterson, will join the band to offer the audience an intimate, anecdote-filled look into her father's exceptional…

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Ronnie, Angie, Bonnie, and Roger: Music in the Round

October 24, 2025 @ 6:00 pm - 10:00 pm
Creative Nomad Studios, 23 Mississaga St W.
Orillia, Ontario L3V 3A5 Canada
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Friday October 24, 2025 Music in the Round with Ronnie Douglas, Angie Nussey, Bonnie Milne, and Roger Harvey proudly presented by Dapper Depot Menswear and Harvey's Orillia Join us for a special evening of songs, discussions on music and songwriting, song inspirations, and collaboration. We are so excited for this special night. This is a NIGHT YOU DO NOT WANT TO MISS! Doors: 6:30pm Music shortly after 7pm TICKETS $19 All Ages and the Event is Licensed 

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Karaoke Night at The Clubhouse

October 24, 2025 @ 7:00 pm - October 25, 2025 @ 12:00 am
The Clubhouse Bar & Golf Sim, 865 West Ridge Blvd
Orillia, ON L3V8B3 Canada
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Karaoke Night @ The Clubhouse Bar & Golf Sim! The biggest and best karaoke in Orillia — don’t miss it! October 24th | 7PM - 12AM 865 Westridge Blvd, Orillia, Ontario$0 Entry Fee Featuring DJ Karaoke Services Call to reserve a table 1-249-202-3462 or 705-879-9995 Bring your friends, grab a drink, and hit the stage!

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Gerry Dee

October 24, 2025 @ 9:00 pm - 11:00 pm
Casino Rama Resort, 5899 Rama Road
Rama, Ontario L3V 6H6 Canada
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Comedian, actor and author Gerry Dee, is back on stage on his new Funny You Should Say That Tour. Dee is currently the host of Family Feud Canada and plays the role of “Templeton Dudge” in the sitcom Animal Control on FOX Television. He was the star and co-creator of the hit CBC comedy Mr.D for 8 seasons and released his first book, “Teaching: It’s Harder Than It Looks,” in 2012 which became a National best seller. Tickets can be purchased at the Box Office or at…

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Roger Harvey w/ Alex Kaye Black

October 25, 2025 @ 7:00 pm - 10:00 pm
Paper Planes Play Cafe, 178 Mississaga Street East
Orillia, Ontario L3V 1V8 Canada
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Saturday October 25, 2025 Roger Harvey with special guest Alex Kaye Black proudly presented by Dapper Depot Menswear and Harvey's Orillia Join us as we welcome Roger Harvey with special guest Alex Kaye Black. Roger Harvey resides in Nashville Tennessee . He is a folk singer from Pennsylvania. Raised in Erie County, Roger Harvey's songs reflect where he came from, where he's been & the better world he's determined to find. Joining Roger is Alex Kaye Black. Alex is a…

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Newfoundland Songbook

October 25, 2025 @ 7:30 pm - 9:30 pm
Orillia Opera House – G.L. Auditorium, 1 West Street North
Orillia, Ontario L3V 5B8 Canada
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The colourful history of Newfoundland's fishers and loggers, sealers and whalers is told with story, song and incredible visuals in this engaging musical review by Shipyard Kitchen Party, creators of Tom Thomson's Wake and 100 Years from Now. From the remote outports to the vibrant city of St. John's, from the fishing stages to the kitchens and front parlours, you'll hear the timeless sea-shanties, triumphant ballads and the hilarious foot-stomping sing-a-longs that make Canada's 10th province its most legendary. You may not be…

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Lightfoot Days Festival

October 30, 2025 - November 2, 2025
Downtown Orillia, 33 Mississaga Street West,
Orillia, Ontario L3V 3A5 Canada
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Lightfoot Days Festival

Please join us, once again, to celebrate the music and legacy of Canada's most-gifted and prolific songwriter, in his hometown of Orillia. This year's Lightfoot Days Festival expands to four days, from Thursday October 30 through Sunday November 2, with live music, storytelling, tours, and special tributes occurring each day. Keep up to date with festival events and features on the Lightfoot Days Festival's Facebook page.

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November 2025

Sarah McLachlan

November 7, 2025 @ 9:00 pm - 11:00 pm
Casino Rama Resort, 5899 Rama Road
Rama, Ontario L3V 6H6 Canada
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Sarah McLachlan is one of the most celebrated singer/songwriters in entertainment with over 40 million albums sold worldwide. She has received three Grammy Awards and twelve Juno Awards over her career and has been inducted into the Canadian Music Hall of Fame. The Fumbling Towards Ecstasy 30th Anniversary Tour celebrates McLachlan’s highly acclaimed third studio album, which first released October 22, 1993. The album quickly topped the charts in Canada and went certified platinum within a few weeks, selling over 3…

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No Great Mischief Live Music at the Hog and Penny

November 8, 2025 @ 9:00 pm - 11:00 pm
Hog & Penny, 9 Matchedash St N
Orillia, Ontario L3V 4T4 Canada
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Our House Band, No Great Mischief, returns for #traditionalsaturday ! Live at The Hog and Penny, this Saturday from 9pm.

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Jet Lips w/ special guests Guilhem & The Bamboo Bones and Brat Stepson

November 13, 2025 @ 6:30 pm - 10:30 pm
Creative Nomad Studios, 23 Mississaga St W.
Orillia, Ontario L3V 3A5 Canada
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Event Details Mandatory Meeting and the Orillia Youth Centre present: November 13, 2025 Creative Nomad Studios located in Downtown Orillia Jet Lips Guilhem & The Bamboo Bones (from Montreal) Brat Stepson sponsored by Dapper Depot Menswear and Harvey's Orillia This is a NIGHT YOU DO NOT WANT TO MISS! Doors: 6:30pm Music shortly after 7pm TICKETS $14 All Ages and the Event is Licensed ***All Proceeds Going Directly to Support Youth Programming at the Orillia Youth Centre***    

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