What’s On in Oakville: October Family-Friendly Events Calendar
October in Oakville is nothing short of magical. Crisp autumn air, cozy sweaters, crunchy leaves, and the buzz of family-friendly fun fill the town. Whether you’re looking for pumpkin patches, harvest festivals, spooky but safe Halloween events, or cultural celebrations, Oakville has something for every age and stage of family life.
As a local real estate broker—and Oakville local—I know families love not just our homes and schools but the community vibe that comes alive every season. This October is packed with events that make it the perfect time to get outdoors, support local businesses, and make memories with your kids.
Here’s your complete family-friendly October events calendar for Oakville. Bookmark it, share it, and most importantly—use it to plan your weekends!
🎃 Pumpkin & Harvest Festivals
Springridge Farm Harvest Festival
When: Weekends in October
Where: Springridge Farm (just outside Oakville)
Details: A fall staple for Oakville families. Enjoy wagon rides, corn trails, pumpkin picking, and barnyard animals.
Bronte Creek Pumpkin Festival
When: Weekends in October
Where: Bronte Creek Provincial Park
Details: Family hikes with the fall colours, kids’ pumpkin activities, and food vendors with local treats.
Oakville Farmers’ Market – Fall Harvest Edition
When: Saturdays in October
Where: Downtown Oakville & Kerr Village
Details: Beyond fresh produce, kids can enjoy live music, face painting, and seasonal crafts.
👻 Halloween Events for Families
Downtown Oakville Trick-or-Treating Spree
When: Saturday, October 26
Where: Downtown Oakville
Details: Local shops open their doors to trick-or-treaters. A safe, walkable way for little ones to enjoy Halloween.
Oakville Museum Haunted Walks
When: Select evenings in October
Where: Erchless Estate
Details: Family-friendly “spooky, not scary” tours exploring Oakville’s historic stories.
Glen Abbey Community Centre Halloween Skate
When: Sunday, October 27
Where: Glen Abbey Rec Centre
Details: Dress up and skate under twinkly lights.
🍂 Cultural & Community Events
Oakville Children’s Festival: Autumn Edition
When: October 12–13
Where: Towne Square, Downtown Oakville
Details: Puppet shows, live music, storytime, and interactive art activities.
KerrFest Fall Celebration
When: October 19
Where: Kerr Village
Details: Family entertainment, local food trucks, and live performances.
Library Fall Reading Challenge
When: All of October
Where: All Oakville Public Library branches
Details: Kids can join autumn-themed reading activities, scavenger hunts, and book prizes.
🌳 Outdoor Adventures in October
Bronte Creek Provincial Park Fall Colour Walks
Sixteen Mile Creek Trail Autumn Hikes
Lions Valley Park family picnics
Encourage families to dress warm, bring thermoses of hot chocolate, and capture those Instagram-worthy fall photos.
🏡 Why Families Love Oakville in October
This season shows why Oakville is one of the most family-friendly communities in the GTA. From parks to rec centres to vibrant local businesses, Oakville combines small-town warmth with big-city amenities.
Thinking about moving to Oakville or upgrading within town? October is a perfect time to explore neighbourhoods while enjoying fall festivities.
At Q Real Estate Group, we live here too—and we’d love to help your family find a home in this amazing community. Reach out anytime to chat about your next move.
