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 weekend at the Erin Fall Fair! Enjoy midway rides, agricultural exhibits, farm animals, local vendors and family-friendly entertainment. Visit https://erinfair.com/ for event details and admission information.

Downey's Farm Pumpkinfest | September 19–October 31 - Celebrate fall with Pumpkinfest at Downey's Farm! Enjoy seasonal activities, pumpkins and plenty of family-friendly autumn fun. Tickets are available online only at https://www.downeysfarm.com/

Sweet Peas Farm - Enjoy a fall farm outing with pumpkins, seasonal displays and photo opportunities. A great way to spend time outdoors and enjoy the autumn season!

Orangeville Farmers' Market | Saturday, October 10 - 8 a.m.–1 p.m. | 2nd Street beside Town Hall

Shop fresh local produce, seasonal favourites, baked goods and more while supporting local farmers and vendors.

LIVE MUSIC & ENTERTAINMENT

Thursday, October 8

• GoodLot: Movie Trivia Night, 7–9 p.m.

• The Hatter: Ryan Hancock, 6:30 p.m.

• Broadway Beat: Jam Night, 6:30 p.m. sign-up

• Tap House: Music Bingo Night, 7–9 p.m.

• Bar on Broadway: Karaoke, 7 p.m.

• Lightcaster: Brett Lawler, live acoustic music, 7–10 p.m.

Friday, October 9

• GoodLot: John Cheesman, 5–7 p.m.

• Tap House: 1990 A.D., 8–11 p.m.

• Broadway Beat: Mid-Life Crisis, 8 p.m.

• Lightcaster: Madchester, 8 p.m.–midnight. No cover!

Saturday, October 10

• GoodLot: Mark Thackway, 4–7 p.m.

• Tap House: DJ T1, 9 p.m.–1 a.m.

• Broadway Beat: Guitars Cadillacs, 8 p.m.

• Lightcaster: 2000s Throwback Party, 8 p.m.–late.

Sunday, October 11

• Mono Centre Brewing: Drew Moore, live music, 2–5 p.m.

• GoodLot: Nick Vescio, 2–5 p.m.

• Broadway Beat: Industry Night Karaoke, 7–11 p.m.

• Lightcaster: Open Mic, 4:30–8:30 p.m.

Monday, October 12 – Thanksgiving

Enjoy the holiday with family and friends! The Erin Fall Fair and Downey's Farm Pumpkinfest offer more ways to enjoy the long weekend.

Wishing everyone a wonderful Thanksgiving long weekend!