Fall Fun Preview: Your Guide to an Epic Autumn
Who says summer has to end just because the calendar says so?
We love to squeeze every last drop out of summer, and with our region’s extended stretch of warm, sunny days, fall is the perfect excuse to keep the fun going. Think crisp mornings, golden vineyards, apple-picking adventures, patio-worthy afternoons and plenty of reasons to get out and explore.
Whether you’re craving a taste of the season, cheering from the stands, getting your scare on or settling in for a great film, there’s no shortage of ways to make this fall one to remember.
Hereβs your Fall Fun Preview packed with events and experiences youβll want on your calendar!
Pick Your Own Fall Adventure
Fall just isn’t fall without getting out on the farm! Grab the family, round up your friends and head out for a day of apple picking, pumpkins, seasonal produce and plenty of fresh-air fun.
Our Pick Your Own Guide makes it easy to find local farms where you can embrace the season and fill your basket with the best of the harvest. Whether you’re planning a family outing or looking for the perfect autumn photo op, there’s plenty to discover.
Explore the Pick Your Own Guide
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Find Your Next Fall Favourite
From festivals and food to live entertainment, family activities and everything in between, there’s always something happening in Windsor Essex.
Our Fall Event Guide is your go-to source for planning your seasonal adventures. Browse upcoming events, make a few plans and start filling that calendar because the hardest part will be deciding what to do first!
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Get a Slice of the Action at Windsor Pizza Festival
Calling all pizza lovers: this one is for you.
The Windsor Pizza Festival is bringing together one of the city’s most beloved culinary traditions with plenty of delicious reasons to dig in. Come hungry, explore participating spots and celebrate the pizza that has helped put Windsor on the foodie map.
Because honestly, is there a better way to spend a fall day than with a hot slice in hand?
Discover the Windsor Pizza Festival
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Raise a Glass at J.P. Wiserβs Whisky Weekend
Fall and whisky? Now that’s a pairing.
Get ready for J.P. Wiserβs Whisky Weekend, a celebration of local whisky, craftsmanship and all the things that make a great autumn experience. It’s a chance to sip, savour and discover more about one of Windsor’s iconic whisky stories.
Gather your whisky-loving crew and make a weekend of it!
Learn More About J.P. Wiserβs Whisky Weekend
Turn Up the Heat at November Meltdown
Who says November has to be chilly? Turn up the heat with November Meltdown!
SAVE THE DATE for a deliciously fall adventure from EPIC Wineries celebrating local wine, food and the flavours of the season. With participating wineries serving up a wine sample paired with a delicious grilled cheese, itβs the perfect excuse to explore the region, discover a new favourite bottle and embrace the cozy side of fall. Tickets on sale October 1st.
Round up your wine-loving friends, bundle up and make a day of it β because fall in Windsor Essex is always tastes better when you’re on an EPIC adventure.
Get Ready for World-Class Hockey
The excitement hits the ice this fall with the 2026 IIHF Womenβs World Championship PreTournament.
Catch top-level women’s hockey as teams take to the ice in Windsor ahead of the championship. Whether you’re a lifelong hockey fan or simply love the energy of a big sporting event, it’s a great reason to get out, cheer loud and experience the action right here in Windsor Essex.
Get the Details on the IIHF Womenβs World Championship PreTournament
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Get Your Scare On at Scarehouse
Want to add a little adrenaline to your autumn adventures?
Scarehouse brings haunted experiences to Windsor for those who like their fall fun with a side of fright. Gather your bravest friends, prepare to scream and see if you can make it through!
And if you’re looking for even more Halloween happenings, be sure to check out our Halloween Event Guide for more seasonal events, activities and ways to celebrate.
Browse the Halloween Event Guide
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Settle In for WIFF
As the leaves change and the days get a little shorter, it’s the perfect time to grab some popcorn and settle in for WIFF β the Windsor International Film Festival.
Celebrating incredible films from around the world, WIFF is one of those fall traditions that gives movie lovers plenty to look forward to. Discover new stories, catch a highly anticipated film and experience the buzz that takes over downtown Windsor during festival season.
Visit the Windsor International Film Festival
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Make This Fall One to Remember, grab your favourite sweater, round up your people and start making plans. Pick apples. Sip whisky. Cheer on hockey. Eat pizza. Catch a film. Get your scare on. Most importantly, get out and explore all that Windsor Essex has to offer this fall.
