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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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September 2026

Couchiching Fest

September 19 - September 20
Port of Orillia, 50 Centennial Dr
Orillia, ON L3V 4M8 Canada
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Couchiching Fest is a vibrant artisan and vendor marketplace celebrating creativity, community, and local small business. Discover handcrafted goods, unique artisan products, delicious treats, and one-of-a-kind finds from talented makers across the region. It’s the perfect way to shop local and experience the spirit of Couchiching! Event Date: September 19-20, 2026 Location: Port of Orillia - 50 Lightfoot Dr, Orillia, ON

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Chappell Farms Fall Festival

September 19 @ 10:00 am - October 31 @ 6:00 pm
Chappell Farms, 617 Penetanguishene Rd.,
Oro-Medonte, Ontario L4M 4Y8 Canada
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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 19th till October 31st Admission includes one pick-your-own pumpkin There is food…

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Autumn Tea at the Leacock Museum

September 20
|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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Summer Music Showcase at Brewery Bay

September 26 @ 12:30 pm - 5:00 pm
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One event on September 19, 2026 at 12:30pm

One event on September 26, 2026 at 12:30pm

Live music on the patio? Sign us up! We have two incredible artists coming in, each performing a two-hour set nearly every Saturday afternoon all summer long! Saturday September 12 12:30pm - 2:30pm - David Owen 3:00pm - 5:00pm - Amy & Kyle Saturday September 19 12:30pm - 2:30pm - Jeremiah Hill 3:00pm - 5:00pm - Vince Therrin Saturday September 26  12:30pm - 2:30pm - Christopher O'connor 3:00pm - 5:00pm - James Higgins No cover; No reservations.

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Oma’s Ride 2026

September 27 @ 8:00 am - 12:00 pm
Quayle’s Brewery, 4567 Line 12 N
Coldwater, Ontario L0K 1E0 Canada
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$50.00 flat fee

The Alzheimer Society of Simcoe County is pleased to announce Oma's Ride will be returning on Sunday, September 27th, 2026 at Quayle's Brewery. Oma’s Ride is a community cycling event bringing together riders, families, friends, sponsors, and supporters for a day of cycling, connection, and community impact. Quayle's Brewery will serve as the heart of Oma's Ride, where participants, volunteers, sponsors, and supporters will come together to register, enjoy refreshments, share in the excitement of the day and celebrate the…

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October 2026

Orillia Fall Fair

October 2 @ 12:00 am - October 4 @ 12:00 am
ODAS Park, 4500 Fairgrounds Rd
Orillia, Ontario L3V 6H2 Canada

Orillia Fall Fair is a beloved annual celebration of community, agriculture and fall fun. Enjoy midway rides, live entertainment, agricultural exhibits, local vendors, competitions, food and activities for the whole family. It’s a great way to soak up the sights, sounds and traditions of the season in Orillia.

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‘If You Could Read My Mind’ Poetry & Music Lawn Night

October 3 @ 5:00 pm - 7:00 pm
Leacock Museum, 50 Museum Dr
Orillia, Ontario L3V 6K5 Canada
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If You Could Read My Mind… Poetry & Music Lawn Night The Orillia Museum of Art & History (OMAH) and the Leacock Museum invite you to an evening of poetry, music, storytelling, and community connection. Inspired by the cultural and literary traditions that continue to shape our region, this collaborative outdoor event celebrates local voices and artistic expression in a relaxed lakeside setting. Bring your own lawn chair and settle in for an evening of live performances surrounded by the…

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Paint by the Lake

October 4 @ 12:00 pm - 2:00 pm
|Recurring Events (See all)

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

One event on October 4, 2026 at 12:00pm

One event on October 11, 2026 at 12:00pm

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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The Haunted Mill

October 9 @ 6:00 pm - 9:00 pm
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An event every week that begins at 6:00pm on Friday and Saturday, repeating until October 31, 2026

An event every week that begins at 6:00pm on Friday and Saturday, repeating until October 31, 2026

The Coldwater Mill, 1 Mill St,
Coldwater, Ontario L0K 1E0 Canada
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$10

Held upstairs at the Coldwater Mill This thriller jump scare walk through is presented by The Scream Shack 6pm to 9pm Fridays and Saturday in October starting October 9, 2026 Tickets are $10 each sold at the door

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The Haunted Mill

October 10 @ 6:00 pm - 9:00 pm
|Recurring Events (See all)

An event every week that begins at 6:00pm on Friday and Saturday, repeating until October 31, 2026

An event every week that begins at 6:00pm on Friday and Saturday, repeating until October 31, 2026

The Coldwater Mill, 1 Mill St,
Coldwater, Ontario L0K 1E0 Canada
+ Google Map
$10

Held upstairs at the Coldwater Mill This thriller jump scare walk through is presented by The Scream Shack 6pm to 9pm Fridays and Saturday in October starting October 9, 2026 Tickets are $10 each sold at the door

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