Community Calendar

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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Theatre Orangeville Summer Arts Fest

Friday, August 8, 2025 - 6:00 pm to 10:00 pm

87 Broadway, Orangeville, ON

In 2025 Summer Arts Fest returns ‘home’ to Orangeville. Come for all of your favourite events; North(519) Best of Toronto Fringe, Music Bingo, KidsFEST and so much more. Stay tuned for ticket on-sale information and more.

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The Iron Mask- North(519) Best of Toronto Fringe

Friday, August 8, 2025 - 7:30 pm to 8:30 pm

87 Broadway, Orangeville, ON

In the smoke-choked backrooms of 1920s Toronto, where jazz and bootleg liquor flow like an untamed river, ’The Man in the Iron Mask is reborn as a Prohibition-era musical. Twins—one, a ruthless crime lord draped in silk and sin; the other, a prisoner lost in the underbelly of King St —are bound by fate and a secret buried i ...

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Me and You and the Highland Coo- North(519) Best of Toronto Fringe

Friday, August 8, 2025 - 9:15 pm to 10:15 pm

87 Broadway, Orangeville, ON

Buckle up because Jackie and Charlie have a plan: road trip across Scotland, find the perfect Highland coo, and definitely not think about their problems back home in Canada. With carpool karaoke, trivia, and too many snacks, what could go wrong? All that’s missing, is you! Starring an award-winning Montreal cast, “Me and ...

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Orangeville Farmers' Market

Saturday, August 9, 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 9, 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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Theatre Orangeville Summer Arts Fest

Saturday, August 9, 2025 - 6:00 pm to 10:00 pm

87 Broadway, Orangeville, ON

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Orangeville ComiCon

Sunday, August 10, 2025 - 10:00 am to 3:00 pm

Orangeville Curling Club, 76 Fifth Avenue, Orangeville, ON

Enjoy a day of fan culture at the Orangeville ComiCon, hosted by POP Culture Canada. The event will offer the opportunity to meet with artists and authors, and shop from a wide range of vendors selling comic books, new and vintage toys, jewelry, DVD's, anime, manga, prints, and more! Attendees are encouraged to join in the ...

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Apothecay- North(519) Best of Toronto Fringe

Sunday, August 10, 2025 - 2:00 pm to 3:00 pm

87 Broadway, Orangeville, ON

In a world built for men, women create community.Within the magical walls of a living sanctuary, situated in neither time nor place, Lady and Tilly work tirelessly and secretly to support all women in need as they appear at their door. Imperfect themselves, our protagonists discover what it means to do good in a world of co ...

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Theatre Orangeville Summer Arts Fest

Sunday, August 10, 2025 - 6:00 pm to 10:00 pm

87 Broadway, Orangeville, ON

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Cruisin’ on First Classic and Custom Car Show

Wednesday, August 13, 2025 - 6:00 pm to 8:30 pm

99 First Street, Orangeville, ON

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Dufferin Film Festival

Friday, August 15, 2025 - 5:00 pm

Opera House, 87 Broadway, Orangeville, ON

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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Dufferin Film Festival

Saturday, August 16, 2025 - 8:00 am

Opera House, 87 Broadway, Orangeville, ON

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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

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Summer Sounds - Live on Broadway

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

87 Broadway, Orangeville, ON

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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

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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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Shop the Sidewalk

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

87 Broadway, Orangeville, ON

Downtown Orangeville’s shopping event of the season is back! Explore downtown’s Shop the Sidewalk event for deals, promotions, one-of-a-kind items, fall previews & more at these locally owned businesses.

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