What's Happening?

Stay in the know with our weekly roundup of events, activities, and local highlights happening in and around Orangeville every weekend. Whether you're looking for a fun outing, a new local restaurant to try, or a way to support small businesses, this is your go-to guide for making the most of your weekend — right here in our community. 

Latest Blog Posts

WHAT’S HAPPENING AROUND ORANGEVILLE: OCTOBER 8–12, 2026

Looking for something to do this Thanksgiving long weekend? From fall fairs and pumpkin festivals to live music, karaoke, local markets and family-friendly activities, there's plenty happening in and around Orangeville! EVENTS & THANKSGIVING WEEKEND FUN Erin Fall Fair | October 9–12 - Celebrate Thanksgiving ...

Posted by The Ginny Anderson Real Estate Team on Oct 08, 2026

What’s Happening This Weekend October 01 - October 04

What’s Happening Around Orangeville: October 01–October 04 Events Downey’s Farm Pumpkinfest | September 19–October 31 Celebrate fall with Pumpkinfest at Downey’s Farm. Tickets are available online only at DowneysFarm.com. Orangeville Farmers’ Market | Saturday, October 3, 8 a.m.–1 p.m. Shop local vendors ...

Posted by The Ginny Anderson Real Estate Team on Oct 01, 2026

What’s Happening in Orangeville: September 17–20

EVENTS Orangeville Farmers’ Market Saturday, September 19 | 8 a.m.–1 p.m. Shop fresh local produce, baked goods and artisan products while supporting local farmers and vendors. Orangeville Oktoberfest Saturday, September 19 | Noon–1 a.m. Mill Street, Downtown Orangeville | Free admission Enjoy a taste ...

Posted by The Ginny Anderson Real Estate Team on Sep 17, 2026

What’s Happening In & Around Orangeville | September 10–13

There’s lots happening in and around Orangeville this weekend! From the Farmers’ Market and live music to trivia, karaoke and more, here’s your weekend lineup. LOCAL EVENTS SATURDAY, SEPTEMBER 12 Orangeville Farmers’ Market – 8AM – Downtown Orangeville, beside Town Hall Maple Syrup Farm Experience – ...

Posted by The Ginny Anderson Real Estate Team on Sep 10, 2026
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