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 30, and there is no fee to attend. Weather permitting.

SEP

Fall Festival Juried Art Show and Sale

Thursday, September 24, 2026 - 10:00 am to 5:00 pm

Alton Mill Arts Centre, 1402 Queen Street West, Alton, Ontario

Fall Festival Art Show and Sale –Sept. 16 – Oct. 4, Wednesday through Sunday, 10 am – 5 pm.

SEP

Fall Festival Juried Art Show and Sale

Friday, September 25, 2026 - 10:00 am to 5:00 pm

Alton Mill Arts Centre, 1402 Queen Street West, Alton, Ontario

Fall Festival Art Show and Sale –Sept. 16 – Oct. 4, Wednesday through Sunday, 10 am – 5 pm.

SEP

Fall Classic Hockey Tournament

Friday, September 25, 2026 - 11:00 am

275 Alder Street, Orangeville, ON

Orangeville Minor Hockey is hosting the 2026 Fall Classic AA & A! Games will be played over a three day tournament at the Alder Recreation Centre and Tony Rose Memorial Sports Centre in Orangeville. Divisions include: U10 AA, U10 A, U11 AA, U11 A, U12 AA, U12 A, U13 AA, U13 A, U14 AA, U14 A, U14 BB, U15 AA, U15 A, U16 AA, ...

SEP

How We Got To Jersey: A Tale of Two Frankies presented by Theatre Orangeville

Friday, September 25, 2026 - 7:30 pm

Theatre Orangeville, 87 Broadway, Orangeville, ON

How We Got To Jersey: A Tale Of Two Frankies is a once-in-a-lifetime opportunity to hear not one, but TWO Frankie Vallis in a showstopping concert revue that takes you behind the scenes of the blockbuster Broadway smash hit, Jersey Boys. Find out how two small-town Canadian kids grew up to BOTH play a bonafide Roc ...

SEP

Orangeville Farmers' Market

Saturday, September 26, 2026 - 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 ...

SEP

Fall Festival Juried Art Show and Sale

Saturday, September 26, 2026 - 10:00 am to 5:00 pm

Alton Mill Arts Centre, 1402 Queen Street West, Alton, Ontario

Fall Festival Art Show and Sale –Sept. 16 – Oct. 4, Wednesday through Sunday, 10 am – 5 pm.

SEP

Fall Classic Hockey Tournament

Saturday, September 26, 2026 - 11:00 am

275 Alder Street, Orangeville, ON

SEP

How We Got To Jersey: A Tale of Two Frankies presented by Theatre Orangeville

Saturday, September 26, 2026 - 7:30 pm

Theatre Orangeville, 87 Broadway, Orangeville, ON

SEP

Fall Festival Juried Art Show and Sale

Sunday, September 27, 2026 - 10:00 am to 5:00 pm

Alton Mill Arts Centre, 1402 Queen Street West, Alton, Ontario

Fall Festival Art Show and Sale –Sept. 16 – Oct. 4, Wednesday through Sunday, 10 am – 5 pm.

SEP

Fall Classic Hockey Tournament

Sunday, September 27, 2026 - 11:00 am

275 Alder Street, Orangeville, ON

SEP

How We Got To Jersey: A Tale of Two Frankies presented by Theatre Orangeville

Sunday, September 27, 2026 - 2:00 pm

Theatre Orangeville, 87 Broadway, Orangeville, ON

SEP

Fall Festival Juried Art Show and Sale

Wednesday, September 30, 2026 - 10:00 am to 5:00 pm

Alton Mill Arts Centre, 1402 Queen Street West, Alton, Ontario

Fall Festival Art Show and Sale –Sept. 16 – Oct. 4, Wednesday through Sunday, 10 am – 5 pm.

SEP

Cruisin’ on First Classic and Custom Car Show

Wednesday, September 30, 2026 - 6:00 pm to 8:30 pm

99 First Street, Orangeville, ON

OCT

Fall Festival Juried Art Show and Sale

Thursday, October 1, 2026 - 10:00 am to 5:00 pm

Alton Mill Arts Centre, 1402 Queen Street West, Alton, Ontario

Fall Festival Art Show and Sale –Sept. 16 – Oct. 4, Wednesday through Sunday, 10 am – 5 pm.

OCT

Orangeville & Area Job Fair

Thursday, October 1, 2026 - 3:00 pm to 7:00 pm

Best Western Plus Orangeville Inn & Suites (7 Buena Vista Drive, Orangeville, Ontario L9W 0A2)

Employer registration is now open for the Orangeville and Area Job Fair Date: Thursday, October 1, 2026 Time: 3 to 7 p.m. Location: Best Western Plus Orangeville Inn & Suites (7 Buena Vista Drive, Orangeville, Ontario L9W 0A2) Details for participating employers The Town of Orangeville’s Economic De ...

OCT

Fall Festival Juried Art Show and Sale

Friday, October 2, 2026 - 10:00 am to 5:00 pm

Alton Mill Arts Centre, 1402 Queen Street West, Alton, Ontario

Fall Festival Art Show and Sale –Sept. 16 – Oct. 4, Wednesday through Sunday, 10 am – 5 pm.

OCT

Orangeville Farmers' Market

Saturday, October 3, 2026 - 8:00 am to 1:00 pm

Beside Town Hall - 87 Broadway, Orangeville, ON

OCT

Dufferin Farm Tour

Saturday, October 3, 2026 - 9:00 am to 4:00 pm

Dufferin County, ON

Take a self-guided tour to gain a glimpse of the diversity of agriculture in the area as host farms share their farming knowledge and the day to day operations and challenges of farming. Dufferin County farms will be showcased, Admision is a non-perishable food donation or cash for the Local Food Bank. This is a rain or shi ...

OCT

Orangeville Antique and Vintage Show

Saturday, October 3, 2026 - 9:00 am to 4:00 pm

OAS Event Centre (Hall A) 247090 Side Road 5, Mono, ON L9W 6K5

For one day, Orangeville becomes the epicentre of the antiques, collectibles and vintage world. Sixty dealers set up indoors at the Fairgrounds. Genuine antiques and vintage, hundreds of categories, in all price ranges. Dealers from all parts of Ontario, plus a few top dealers from Quebec, selliing everything from vintag ...

OCT