Community Calendar

The Dufferin Film Festival celebrates Canadian independent cinema. The programme will feature a series of Canadian made short films in all genres while shining a spotlight on Canadian Indie Filmmakers in the process. The festival aims to inspire, educate and connect filmmakers as well as provide an opportunity for film enth ...

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Orangeville Farmers' Market

Saturday, August 16, 2025 - 8:00 am to 1:00 pm

Beside Town Hall - 87 Broadway, Orangeville, ON

The Orangeville Farmers' Market offers the best in fresh produce, fruits, locally raised meats, fish, flowers, home baked goods and unique artisan crafts. Located directly beside Town Hall on Second Street, the market features free weekly draws, live entertainment, special events, and activities for children.Visit downtowno ...

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Summer Sounds - Live on Broadway

Saturday, August 16, 2025 - 11:30 am to 3:00 pm

87 Broadway, Orangeville, ON

Summer Sounds - Live on Broadway will celebrate local musical talent every Saturday from July 19 to August 30 in three locations. Check Downtown Orangeville BIA website for artist schedule and locations.

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Dufferin Film Festival

Sunday, August 17, 2025 - 8:00 am

Opera House, 87 Broadway, Orangeville, ON

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Cruisin’ on First Classic and Custom Car Show

Wednesday, August 20, 2025 - 6:00 pm to 8:30 pm

99 First Street, Orangeville, ON

The family friendly cruise nights, features classic cars and trucks as well as custom rides on display at the Canadian Tire parking lot in Orangeville. The show takes place every Wednesday night until September 24, and there is no fee to attend. Weather permitting.

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The Great Benjamins Circus

Friday, August 22, 2025 - 11:00 am

Orangeville Fairgrounds, 247090 5th Sideroad, Mono, ON

The Great Benjamins Circus is a family-friendly event aimed at providing a memorable experience for the whole family! Audiences will be treated to: high-flying aerial acts head-spinning jugglers death-defying high-speed motorbikes in the cage of death stunning acrobatics, hilarious clowns, and more. Advance ticket purchase ...

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The Great Benjamins Circus

Friday, August 22, 2025 - 1:30 pm

Orangeville Fairgrounds, 247090 5th Sideroad, Mono, ON

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The Neverending Story

Friday, August 22, 2025 - 7:30 pm

87 Broadway, Orangeville, ON

The Neverending Story Novel written by Michael Ende Play dramatized by David S. Craig Directed by: Pat Rundell Theatre Orangeville -Young Company The story begins with Bastian, a lonely boy, who stumbles into a curious bookshop where he discovers a curious book—The Neverending Story. Bastian hides in the attic of his s ...

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Orangeville Farmers' Market

Saturday, August 23, 2025 - 8:00 am to 1:00 pm

Beside Town Hall - 87 Broadway, Orangeville, ON

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The Mullet Sale - Sidewalk sale up front. Massive markdowns out back.

Saturday, August 23, 2025 - 8:00 am to 2:00 pm

87 Broadway, Orangeville, ON

The Mullet Sale Sidewalk Sale up front. Massive Markdowns out back. It’s a classic sidewalk sale up front—sales tables and racks set up right outside your favourite shops—and out back, it’s all about bold markdowns in Downtown Orangeville’s laneways, private lots, and hidden corners. A little gritty, totally fun, and f ...

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The Mom Market

Saturday, August 23, 2025 - 11:00 am to 4:00 pm

Orangeville Curling Club, 76 Fifth Avenue, Orangeville, ON

Get ready to get your shop on! Bringing Dufferin County, family friendly pop-up markets featuring the best of local artisans, makers and creatives!

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The Great Benjamins Circus

Saturday, August 23, 2025 - 11:00 am

Orangeville Fairgrounds, 247090 5th Sideroad, Mono, ON

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Summer Sounds - Live on Broadway

Saturday, August 23, 2025 - 11:30 am to 3:00 pm

87 Broadway, Orangeville, ON

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The Great Benjamins Circus

Saturday, August 23, 2025 - 1:30 pm

Orangeville Fairgrounds, 247090 5th Sideroad, Mono, ON

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The Neverending Story

Saturday, August 23, 2025 - 2:00 pm

87 Broadway, Orangeville, ON

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The Fulcrum Book Launch with Author Michael Decter

Saturday, August 23, 2025 - 2:00 pm to 3:00 pm

Booklore, 121 First St Orangeville, Ontario L9W

Celebrate the release of this gripping eco-thriller by acclaimed author Michael Decter. Meet the author, enjoy a reading and discussion, and mingle over light, nonalcoholic refreshments. Decter, a Harvard graduate and Order of Canada recipient, brings decades of experience in public policy and research to this timely, high- ...

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Caledon Music Festival 2025: 'A journey into Cabaret and Broadway'

Saturday, August 23, 2025 - 7:30 pm to 9:00 pm

247 Broadway, Orangeville, ON L9W 2Z5

‘A journey into Cabaret and Broadway’ Sat, Aug 23rd, 7:30PM | Westminster United Church in Orangeville Experience the richness and depth of the piano trio genre featuring the exceptional talents of Violinist Luri Lee, Cellist Peter Eom, and Pianist Joonghun Cho. Audiences can anticipate an evening of profound artistry ...

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The Neverending Story

Saturday, August 23, 2025 - 7:30 pm

87 Broadway, Orangeville, ON

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The Great Benjamins Circus

Saturday, August 23, 2025 - 7:30 pm

Orangeville Fairgrounds, 247090 5th Sideroad, Mono, ON

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The Great Benjamins Circus

Sunday, August 24, 2025 - 11:00 am

Orangeville Fairgrounds, 247090 5th Sideroad, Mono, ON

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The Great Benjamins Circus

Sunday, August 24, 2025 - 1:30 pm

Orangeville Fairgrounds, 247090 5th Sideroad, Mono, ON

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The Neverending Story

Sunday, August 24, 2025 - 2:00 pm

87 Broadway, Orangeville, ON

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Cruisin’ on First Classic and Custom Car Show

Wednesday, August 27, 2025 - 6:00 pm to 8:30 pm

99 First Street, Orangeville, ON

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The Orangeville Fall Fair

Friday, August 29, 2025 - 4:00 pm to 11:00 pm

OAS Event Centre 247090 Side Road 5, Mono, ON L9W 6K5

The Orangeville Fair returns on Labour Day weekend. It's the perfect family outing and offers a wide variety of activities and events. A demolition derby, tractor pulls, live music, food trucks, local vendors, and so much more will round out your fair experience. Save the date for family fun and watch for more details comi ...

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