Upcoming Events

The Headwaters Arts Fall Festival is a celebration of art, culture and community. This year is especially exciting, marking the 30th anniversary! The event includes the Juried Art Show and Sale, Opening Soiree, Jurors Walk,  and other artful events. It showcases and celebrates the vast array of artistic talent that Ontario has to offer.

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Come on down to the Brampton Fall Fair, located in Caledon for a day of nostalgic fun! Attractions include rides, the demolition derby, mini chuckwagon races, agricultural competitions, arts & crafts and so much more! 

Join Caledon Hills Brewing Co for their annual Oktoberfest celebration! Get in on the fun with German food and beer, live music and stein-holding competitions! Don't miss the biggest party of the year this September 18th-20th!

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Fall is calling! Mark your calendars for the return of Pumpkinfest at Downey's Farm. From September 19 to October 31, wander through thousands of pumpkins, play in the Pumpkinfest Play Area, enjoy live music, wagon rides, seasonal treats and more! Tickets must be purchased in advance online.

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First Tee – Ontario invites you to celebrate their inaugural Backyard Bash presented by Himilayas Golf. Located at the Talon Links Golf Canada Putting Park, this event is fun for the whole family! Enjoy the Talon Links putting course, food stations, lawn games, giveaways, challenges and more! The event runs from 3-7pm.

New for 2026, Caledon Under the Stars will kick off the Caledon Creative Arts Festival weekend on Friday, September 25, with an evening of live music, a theatre performance, refreshments and arts-focused activities under the stars.

Celebrate the first weekend of fall with the annual Bolton Fall Fair in Caledon! Experience the nostalgia of delicious food, thrilling rides, fun games and engaging agricultural exhibits! Catch the chili cook off, SuperDogs Show, petting zoo...and don't miss out on the infamous DEMO DERBY! See you at the fair.

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The Caledon Creative Arts Festival is back for its FIFTH year! Join artists from Caledon and its neighbouring communities as they gather to bring you an artisan market, live music, authors, workshops and visual art showcase in a beautiful outdoor venue located near the Caledon Trailway and downtown Caledon East. This FREE event is family and pet-friendly, celebrating Ontario Culture Days and Caledon's creative talent. Immerse yourself in a day of art outdoors!

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Join Davis Family Farm for two days of fun this fall! The Creep & Crop Fall Fest is a cozy (and a little spooky) fall celebration. The farm will have a vendor market full of local artists, makers, and seasonal goodies. It's also the perfect day to pick your pumpkin (and squash)!

Explore the stunning fall forest at Terra Cotta Conservation Area by wagon ride! On this interactive guided tour, participants will experience the beauty of autumn and learn about the intriguing transformations that occur in nature. Wagon rides are available to book on fall weekends and holidays. Groups can reserve up to 20 people per reservation.

The Caledon Studio Tour is BACK on October 3rd and 4th. With multiple stops across the Town of Caledon and countless artists to see, this self-guided weekend-long tour gets you up close and personal with the artist process. Experience behind-the-scenes looks at tools, tricks and processes and take the opportunity to purchase one-of-a-kind works directly from the artist. Hit the road with your favourite art lovers and spend the weekend in Caledon.

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Experience the world at Caledon's third annual multicultural festival! Sample international cuisine, enjoy dynamic performances, and participate in crafts and activities with IDEA Caledon's celebration of global cultures. Experience Culture Fest this fall, and get to know Caledon's diverse cultural heritage.

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Farmer's Nightmare is back! Join Rusty Jade Ranch this October for another haunted forest walk at Trinity's Well. Starting at 6:30PM, the scary level will get increasingly spooky each half hour. By the end of the night, it will be terrifying. If you have little ones, we advise you to choose the earlier time slots. Each walk is a duration of 30 minutes. Come on out to the farm to conquer the farmer's nightmare. Do you have what it takes?

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Join Cambium Farms for a magical, mysterious and witchy two days at their Renaissance Faire. Fun on the farm will include vendors and fantasy merchants, sword fighting demos, live magic performances, axe throwing and archery, character encounters, Celtic music, and much more. Stop by the food trucks for a bite, or drinks at the bar! Costume contests and immersive experiences will be waiting for you throughout the event. Saturday from 9-11pm will have a DJ dance (ages 19+ for this portion). See below for more info.

The Town of Caledon is excited to celebrate the Festival of Lights at the Brampton Fairgrounds. On Saturday, November 7, from 6-9pm, our award-winning Diwali Drone Show will return, featuring over 200 drones illuminating the night sky with dazzling displays of symbols that reflect the spirit and traditions of Diwali. This event is weather dependent. The rain date is Sunday, November 8.

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