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.

Loading Events
Find Events

Categories & Audience

Region

Past Events › Everyone

List View | Month View

Events List Navigation

October 2025

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
+ Google Map

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 

Find out more »

Downtown Orillia BIA presents: Monster March!

October 25, 2025 @ 11:00 am - 1:00 pm
Downtown Orillia, 33 Mississaga Street West,
Orillia, Ontario L3V 3A5 Canada
+ Google Map

Dress up in your spookiest costumes and come march with us down Mississaga Street! Meeting will take place by Municipal Lot 5 (beside Plum Loco), and will depart at 11am sharp! Stick around after the march for local Trick or Treating! A list of all participating business will be provided during the march! Hope to see you there!

Find out more »

Ghost Walks

October 25, 2025 @ 6:00 pm - 8:00 pm
|Recurring Events (See all)

One event on October 18, 2025 at 6:00pm

One event on October 24, 2025 at 6:00pm

One event on October 25, 2025 at 6:00pm

Leacock Museum, 50 Museum Dr
Orillia, Ontario L3V 6K5 Canada
+ Google Map

The Leacock Museum is back with our wildly popular Ghost Walks on the Leacock Museum Grounds! Join us for our biggest year yet with surprise guests, treats, and haunted happenings on historical Old Brewery Bay that will leave you with goosebumps, including a jaunt into the haunted basement! Ghost walks take place on the grounds of the Leacock Museum, so please dress appropriately for the weather. Original limestone pathways, stairs and muddy conditions may cause barriers to mobility. For more information,…

Find out more »

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
+ Google Map

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…

Find out more »

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
+ Google Map

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…

Find out more »

The Rock to Fake Pocket Show Skatepark Halloween Party

October 26, 2025 @ 4:00 pm - 6:00 pm

Come have some Halloween fun at the Orillia Skate Park! There will be pizza, candy, prizes, sk8 challenges & a costume contest. Costumes are mandatory! All skaters welcome!

Find out more »

Quayles Fall Fest

October 29, 2025 - October 31, 2025
Quayle’s Brewery, 4567 Line 12 N
Coldwater, Ontario L0K 1E0 Canada
+ Google Map

Quayle’s Brewery Fall Fest is the perfect way to celebrate the season! Nestled among rolling hills and golden fields, this annual event brings together crisp craft brews, live music, local food, and cozy autumn vibes. Stroll the scenic grounds, sip a seasonal pint, and enjoy a day filled with great company and festive fun. Whether you’re here for the beer, the music, or the fall atmosphere, Quayle’s Fall Fest is a can’t-miss celebration of harvest season in the heart of…

Find out more »

Chappell Farms Fall Festival

October 29, 2025 - October 31, 2025
Chappell Farms, 617 Penetanguishene Rd.,
Oro-Medonte, Ontario L4M 4Y8 Canada
+ Google Map

From late September all the way until Halloween, Chappell Farms offers our Fall Festival! It’s an amazing place for kids and adults alike! Come visit our animals, run up to our amazing lookout, explore the sunflower maze, ride on the tricycle track and pick your perfect pumpkin. There is plenty of room to just run and play in the fresh air! Open 10 am- 6 pm daily September 20th till October 31st Admission includes one pick-your-own pumpkin There is food…

Find out more »

Trivia Night

October 30, 2025 @ 7:00 pm - 9:00 pm
Brewery Bay Food Co., 117 Mississaga St. E.
Orillia, Ontario L3V 1V6 Canada
+ Google Map

Time & Location Time & Location Oct 30, 2025, 7:00 p.m. – 9:00 p.m. Higher Ground (Brewery Bay 2nd Floor), 162 Mississaga St E, Orillia, ON L3V 1V9, Canada About the event BOOK YOUR TABLE HERE   Adam of Big Dumb Face Trivia graces the halls of our fine establishment with a night of fun team trivia!   Hosted on Higher Ground (our second-floor event space), Adam will lead you and your clever crew through rounds of hilarious and various…

Find out more »

Trivia Thursday at Crazy Horse: Horseshoe Valley Resort

October 30, 2025 @ 7:30 pm
|Recurring Events (See all)

An event every week that begins at 7:30pm on Thursday, repeating until December 25, 2025

Horseshoe Resort Events

Trivia Thursday at Crazy Horse Restaurant Join us for trivia on Thursday night! Enjoy tasty eats at Crazy Horse with your friends or family and enjoy a night of quizzical fun! The game starts at 7:30pm – we recommend arriving 10-15 minutes prior to secure your table.Questions will cover a wide variety of general topics. All questions are reviewed by our team to ensure they are family-friendly.

Find out more »
+ Export Events

Stay up-to-date on events, packages and things to do, sign up to our newsletter!

No commitments, cancel anytime