Community Calendar

Get ready to sparkle and celebrate at the Joy and Lights Festival – Merry & Bright Weekend, lighting up Downtown Orangeville from November 21-23, 2025! This magical weekend is the crown jewel of Orangeville’s two-week holiday celebration. It will be a dazzling mix of lights, laughter, and festive cheer. Wander through the ...

NOV

Joy and Lights Holiday Gift Market

Friday, November 21, 2025 - 12:00 pm to 8:00 pm

87 Broadway, Orangeville, ON

Step into a winter wonderland at Downtown Orangeville’s Joy & Lights Holiday Gift Market. Inspired by the charming European Christmas markets, this magical outdoor market features handcrafted holiday treasures by talented artisans, delectable holiday treats, festive music and live entertainment. Visits with Santa Stroll thr ...

NOV

Joy and Lights Holiday Gift Market

Friday, November 21, 2025 - 12:00 pm to 8:30 pm

87 Broadway, Orangeville, ON

NOV

Joy and Lights Tree Lighting and Starlight Shopping

Friday, November 21, 2025 - 5:30 pm to 8:30 pm

87 Broadway, Orangeville, ON

Join us for an enchanting evening filled with hometown holiday spirit! Watch the magic unfold as Santa himself lights the town’s beautiful holiday tree, followed by visits with Santa on Second Street! Take in the festive Holiday Market, twinkling window displays, festive caroling, and the delightful hometown charm of beauti ...

NOV

Orangeville HollyFest

Saturday, November 22, 2025 - 9:00 am to 4:00 pm

Orangeville Fairgrounds, 247090 5th Sideroad, Mono

We’re decking the halls and inviting YOU to be part of a magical holiday shopping experience.

NOV

Winter Farmers' Market

Saturday, November 22, 2025 - 9:00 am to 1:00 pm

87 Broadway, Orangeville, ON

The Orangeville Farmers' Market offers local goods all year round. Throughout the winter, the market will run weekly inside Town Hall and feature a rotating selection of local vendors. Visit downtownorangeville.ca for a list of participating vendors each week.

NOV

Joy and Lights Holiday Gift Market

Saturday, November 22, 2025 - 11:00 am to 7:00 pm

87 Broadway, Orangeville, ON

NOV

Joy and Lights Merry and Bright Weekend

Saturday, November 22, 2025 - 12:00 pm to 8:00 pm

87 Broadway, Orangeville, ON

NOV

Santa Claus Parade

Saturday, November 22, 2025 - 5:00 pm to 6:00 pm

87 Broadway, Orangeville, ON

Gather family and friends to see the jolly old elf and make some merry memories at the Orangeville Santa Claus Parade! Come early to shop, marvel at the Yuletide window displays, grab a hot chocolate or bite to eat, and enjoy pre-parade.

NOV

Orangeville HollyFest

Sunday, November 23, 2025 - 10:00 am to 3:00 pm

Orangeville Fairgrounds, 247090 5th Sideroad, Mono

We’re decking the halls and inviting YOU to be part of a magical holiday shopping experience.

NOV

Joy and Lights Holiday Gift Market

Sunday, November 23, 2025 - 11:00 am to 4:00 pm

87 Broadway, Orangeville, ON

NOV

Joy and Lights Merry and Bright Weekend

Sunday, November 23, 2025 - 12:00 pm to 8:00 pm

87 Broadway, Orangeville, ON

NOV

Authors on Stage - Alan Doyle

Sunday, November 23, 2025 - 7:00 pm

87 Broadway, Orangeville, ON

Don’t miss the latest in the Authors on Stage series, an evening with Alan Doyle. In discussion with moderator Bernadette Hardaker, we discuss his book, The Smiling Land. Presented by Theatre Orangeville and Booklore.

NOV

Rapunzel: A Braid New World

Thursday, November 27, 2025 - 2:00 pm

Theatre Orangeville, 87 Broadway, Orangeville, ON

RAPUNZEL: A Braid New World! Yes, that’s right, in keeping with tradition, the panto returns! Fun! Music! Comedy! Fun! Booing! Cheering! Fun! Dancing! Intrigue! Even more fun! And... hair products! Treat yourself, your family and friends to this delightful (and fractured!) romp through one of your most beloved classic ...

NOV

Rapunzel: A Braid New World

Thursday, November 27, 2025 - 7:30 pm

Theatre Orangeville, 87 Broadway, Orangeville, ON

NOV

Joy and Lights Holiday Gift Market

Friday, November 28, 2025 - 12:00 pm to 8:00 pm

87 Broadway, Orangeville, ON

NOV

Joy and Lights Firelight and Frost Weekend

Friday, November 28, 2025 - 12:00 pm to 8:00 pm

87 Broadway, Orangeville, ON

Get ready to experience the magic of the Joy and Lights Festival – Firelight & Frost Weekend in Downtown Orangeville, lighting up the town from November 28–30, 2025! This sparkling celebration is the grand finale of Orangeville’s two-week holiday extravaganza, and it’s bursting with festive cheer. Stroll through the encha ...

NOV

Rapunzel: A Braid New World

Friday, November 28, 2025 - 7:30 pm

Theatre Orangeville, 87 Broadway, Orangeville, ON

NOV

Winter Farmers' Market

Saturday, November 29, 2025 - 9:00 am to 1:00 pm

87 Broadway, Orangeville, ON

NOV

Joy and Lights Firelight and Frost Weekend

Saturday, November 29, 2025 - 11:00 am to 7:00 pm

87 Broadway, Orangeville, ON

NOV

Joy and Lights Holiday Gift Market

Saturday, November 29, 2025 - 11:00 am to 7:00 pm

87 Broadway, Orangeville, ON

NOV

Orangeville Show Chorus Hallmark(ish) Christmas Show

Saturday, November 29, 2025 - 1:00 pm

Westminster United Church, 247 Broadway, Orangeville

Orangeville Show Chorus engages women in the joyful pursuit of musical excellence in four-part harmony a cappella singing to inspire, educate and entertain.

NOV

Orangeville Show Chorus Hallmark(ish) Christmas Show

Saturday, November 29, 2025 - 4:00 pm

Westminster United Church, 247 Broadway, Orangeville

Orangeville Show Chorus engages women in the joyful pursuit of musical excellence in four-part harmony a cappella singing to inspire, educate and entertain.

NOV