Orono Fall Fair Painter

FALL for These Festive Events

As the fall season arrives, so do the events in York Durham Headwaters! Enjoy returning favorites and exciting new additions. Plan a road trip to experience these events and make the most of the season by connecting with family and friends.

York Region

Little Kids at Halloween

Family Fall and Spooky Halloween Events at Black Creek Pioneer Village

September – November

Standing in The Doorway at Markham Museum

Coming September 2023

Schomberg Street Gallery

September 17th

Halloween Haunt at Canada’s Wonderland

September 22nd – October 29th

Camp Spooky at Canada’s Wonderland

Saturdays and Sundays from September 23rd – October 29th 

Markham Fair

September 29th – October 1st

Farm to Fork East Gwillimbury

September 30

Colours of Fall Concert in Aurora

October 5th

Screamers in Vaughan

Thursday – Sunday in October

Richmond Hill Pumpkin Fest

October 7th – 9th

Haunted Halloween at Sharon Temple

October 27th


Girl with Apple

The MONSTER in Oshawa

September 8th – 9th

Drive Festival at Canadian Tire Motorpark

September 8th – 10th

Brooklin Harvest Festival

September 16th

Food Truck Festival in Oshawa

September 17th

Uxbridge Studio Tour

September 19th

Culture Days in Port Perry

September 22nd – 23rd

Winding Roads Music Festival – Featuring Washboard Union

September 23rd

Feargrounds Haunted Attraction in Uxbridge

October 5th – 29th

Pumpkinville in Ajax

October 14th

The Book Drunkard Festival

October 17th – November 12th

Fall Fling in Pickering

October 21st & October 28th



Beekeeping and/or Mead Tasting at Ontario Honey Creations

Weekends in September

Theatre Orangeville and Whiskey Jack presents Stories & Songs of Stompin’ Tom

September 15th – 17th

Wine Cheese and Jazz and Island Lake Conservation Area & Belfountain Conservation Area

September 16th & September 23rd

Sweet Peas Farm Pumpkinfest

September 17th – October 31st

International Plowing Match

September 19th – 23rd

Downey’s Pumpkinfest

September 23rd – October 31st

Dufferin Farm Tour

September 30th

Artesian Craft Market at Sprit Tree Cider

Oct 21st & Nov 18th

Orangeville Farmers Market Boo on Broadway

October 21st

Maple Grove Farm and Market Fall Festival

Throughout September and October

For more events in YDH, visit our events calendar!

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