Community Calendar

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

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 ...

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

Fall Festival Juried Art Show and Sale

Saturday, October 3, 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

Fall Festival Juried Art Show and Sale

Sunday, October 4, 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

Bruce Trail Day - Music Walk @ Splitrock Narrows Nature Reserve

Sunday, October 4, 2026 - 10:00 am to 2:00 pm

Splitrock Narrows Nature Reserve, 755437 2nd Line EHS, Mono

Enjoy live musical performances from a variety of local artists as you wander through the forest. There are activities suitable for all family members, including a Treasure Hike, a Children's Music Circle, and a free BBQ No pre-registration is required, and admission is free! For more information visit the Bruce Trail ...

OCT

Authors on Stage Ben Macintyre

Sunday, October 4, 2026 - 7:00 pm

Theatre Orangeville, 87 Broadway, Orangeville, ON

One of the world’s most celebrated writers of espionage history is coming to Orangeville. Join Theatre Orangeville and BookLore for an unforgettable evening with bestselling British author and historian Ben Macintyre, whose remarkable ability to transform meticulously researched history into gripping, page-turning storyte ...

OCT

Monday Night at the Movies

Monday, October 5, 2026 - 4:30 pm

85 Fifth Avenue, Orangeville

Monday Night at the Movies is a non-profit organization running in partnership with the Film Circuit, a division of the Toronto International Film Festival Group. Founded in 1989, Film Circuit is TIFF’s successful film outreach programme, bringing the best of Canadian and international films and artists to communities acros ...

OCT

Monday Night at the Movies

Monday, October 5, 2026 - 7:00 pm

85 Fifth Avenue, Orangeville

OCT

Monday Night at the Movies

Monday, October 5, 2026 - 9:10 pm

85 Fifth Avenue, Orangeville

OCT

Orangeville Farmers' Market

Saturday, October 10, 2026 - 8:00 am to 1:00 pm

Beside Town Hall - 87 Broadway, Orangeville, ON

OCT

Orangeville and District Horticultural Monthly Meeting

Tuesday, October 13, 2026 - 6:30 pm to 8:30 pm

Orangeville Senior Centre, 26 Bythia St., Orangeville On, L9W 2S1

Please welcome our guest speaker tonight, Paul Judge, as he talks about "A Gardeners Winter." Discover the things you can do for your garden even in winter. Guests are welcome, free parking, sharing table, bring a mug for refreshments.

OCT

Love is For Poor People | Or You Can Do Nothing presented by Theatre Orangeville

Wednesday, October 14, 2026 - 7:30 pm

Theatre Orangeville, 87 Broadway, Orangeville, ON

This double bill of witty one-act plays delivers two sharply observed and delightfully offbeat stories. In Love is for Poor People a forthright and glamorous woman of the world presents a candid look back at the trajectory of her long and eventful life, despite the fact the she’s still quite young and has yet to ...

OCT

Love is For Poor People | Or You Can Do Nothing presented by Theatre Orangeville

Thursday, October 15, 2026 - 7:30 pm

Theatre Orangeville, 87 Broadway, Orangeville, ON

OCT

Quilts at the Park - DPQG Quilt Show

Friday, October 16, 2026 - 10:00 am to 6:00 pm

Monora Park - 500 Monora Park Dr, Mono ON L9W 1Z2

The Dufferin Piecemakers Quilting Guild is proud to once again present their member's work. The quilt show will include: Display of beautiful quilts and quilted items Raffle with three fabulous prizes Mini Draw with a variety of quilted hangings and mats Boutique with wide assortment of items made by members Vendors f ...

OCT

Quilts at the Park - DPQG Quilt Show

Friday, October 16, 2026 - 10:00 am to 6:00 pm

Monora Park - 500 Monora Park Dr, Mono ON L9W 1Z2

OCT

Love is For Poor People | Or You Can Do Nothing presented by Theatre Orangeville

Friday, October 16, 2026 - 7:30 pm

Theatre Orangeville, 87 Broadway, Orangeville, ON

OCT

Orangeville Farmers' Market

Saturday, October 17, 2026 - 8:00 am to 1:00 pm

Beside Town Hall - 87 Broadway, Orangeville, ON

OCT

Bruce Trail Club - Boyne Valley 25K Challenge Hike

Saturday, October 17, 2026 - 8:30 am to 5:00 pm

The hike begins at the Bruce Trail Mulmur Hills Parking Lot (1st Line East #716553, Mulmur, ON)

It's time for the annual Dufferin Hi-Land Bruce Trail Club (DHBTC) Boyne Valley 25 km Challenge Hike! Rally your friends and family and get ready to hike, laugh, sweat, and conquer 25 km through the picturesque and peaceful Boyne Valley. The goal? Complete the challenge. Earn the badge. Make some memories. Lace up. Brin ...

OCT

Boo on Broadway (and beyond)

Saturday, October 17, 2026 - 9:00 am to 1:00 pm

87 Broadway, ON

Join us for Boo! on Broadway and beyond, Downtown Orangeville’s most spooktacular day! Enjoy tiny tots trick or treating, petting zoo, pony rides, jack-o-lantern display and fun contests. Of course, we also have Spooky Sidewalks, Witchy Scavenger Walk, a Town-wide self-directed Halloween Haunt driving tour and an authentic ...

OCT