October 1st, 2025 | Community

A Celebration of Fall in Uxbridge, Ontario

Share This Post:
A Celebration of Fall in Uxbridge, Ontario

Four seasons of beauty are one of many reasons we love Uxbridge, Ontario so much. Glorious warm summers, lively springs, and pristine winters are all part of the package. Nevertheless, there is something particularly magical about fall.

The autumn months are synonymous with pumpkin spice lattes, leaves changing colour, long walks through crisp forests, and the beautiful fall scenery Canada is so famous for. In Uxbridge, the season is accompanied by a never-ending series of fun events, many of which we look forward to each and every year. In this post, we will highlight a few events you can mark on your calendar for years to come.

What’s the latest in Uxbridge real estate? You can stay ahead of the curve and even get access to our newest listings by subscribing to our newsletter.

Uxbridge Fall Fair

The Uxbridge Fall Fair returns every September, with a non-stop series of fun activities and events. Scavenger hunts, baked goods, contests, gardening shows, live music, talent shows, and more all combine to create a beloved tradition now and forever. This is also your opportunity to pick up a completely unique gift or home décor piece that is handmade with love.

Does Uxbridge sound like a great place to start searching for your next home? You just might find your perfect dream house here in our featured listings.

Leaskdale Loop

Pop quiz of the day: what do you love most — fall festivals, visiting pumpkin patches, art, scenery, visiting historical sites, farmers markets, or enjoying the finest foods from artisans? Fortunately, the answer is you don’t have to decide, thanks to the Leaskdale Loop.

You can enjoy it all in a relaxing self-guided driving tour just minutes from Uxbridge. The loop begins on the second Saturday of the month in June and continues until the middle of November, when the long-awaited Christmas market rolls into town.


Does all this talk about Uxbridge events have you curious to learn more? Discover even more to love in the posts below:


Pumpkin Festival

Grab your coat, bring your appetite, and perhaps put on your favourite costume — it is time for the event of the season at the Pumpkin Festival at Uxbridge Farmers’ Market, sponsored by our very own Cindy Wood!

It’s not just about the food or the decoratively creative pumpkins and gourds — there’s also face painting, fun games, the petting zoo, where you can admire adorable animals, and a delightfully spooky Halloween scavenger hunt. This is a fantastic way to kick off the cooler season.

BIA Ladies Night

Girls’ Night! The Business Improvement Area of Uxbridge comes alive with glitter, shopping, raffles, cowboy boots (and other fashion) and, of course, plenty of great food and refreshing drinks.

It’s a great time to bond with your inner circle, and perhaps meet a new bestie. And did we mention the discounts? Several of Uxbridge’s favourite retailers will offer superb specials throughout this event.

BIA Spooky Saturday

Trick-or-treat comes early in downtown Uxbridge! The little ones are ecstatic to not have to wait until October 31 to get their goodies. Many of Uxbridge’s local shops will be handing out sweets, chips, and other delights to children of all ages, dressed up in costumes. Think of it like a dress rehearsal for the main event.

Fright Night at the Uxbridge Historical Centre

For a small admission fee, you can have the socks scared right off your feet at the Uxbridge Historical Centre’s Fright Night. This evening does not disappoint as it is filled with spooks, ghouls, ghosts, and most importantly of all, tasty treats. That’s why we simply cannot wait to attend year after year.

Jazz in Leaskdale

As October draws to a close, we head on back to Leaskdale for some toe-tapping jazz music. Admission is free, but donations are appreciated. Light refreshments are also available to restore your energy as you clap along to the beat.

Sunday Farmers’ Market in Uxbridge

Who can resist a farmers’ market? Certainly not us, and the Sunday market in Uxbridge takes the celebration of local to a new level. Though it begins in May, it goes all the way to the end of October, making it one of our favourite autumn traditions.

This is your chance to shop fresh produce, sample some tasty artisanal foods, and pick up a stunning piece of handcrafted art. With more than 50 local vendors featured each week, and live music and kids’ activities, there is something for everyone.

If ever there was a reason to get up early on a Sunday morning, this is it. Note: the market is also dog friendly, so your leashed pal is welcome to join you as you sample the local goodies.

Fall Book Drunkard Festival

At the Cindy Wood Team, we are all addicts: to books, of course! We simply cannot get enough of great reads, which is why the Fall Book Drunkard Festival is one for the calendar.

Here is your chance to get a signed copy of your favourite book, and perhaps even meet the author. You can even get a voucher to use long after this event is over.


Are you planning a move? The posts below can help you strategize when buying a home:


Santa Claus Parade

Cool days of autumn turn into winter and usher in what may be the most exciting event of all. Uxbridge’s Santa Claus Parade is not to be missed.

Traditionally, it takes place on the third Sunday of November every year, and this just might be the best 1 ½ hours of your life! The parade begins at the arena on Brock St. West, and then continues through downtown and heads all the way to Uxbridge Secondary School.

This parade has been one of Uxbridge’s most beloved traditions since 1961. So grab a hot chocolate and take in the sounds of the big band as you await the arrival of the man in red himself.

Other Outstanding Uxbridge Events

Many of our favourite events aren’t necessarily limited to fall, and yet, you couldn’t ask for a better time to enjoy them. It could be a stroll through downtown Uxbridge as you pop in and out of all of the little independent shops and restaurants. Or, you may indulge in Uxbridge’s walking trails, which are among the most beautiful in the GTA. Would you expect anything less from the official “Trail Capital of Canada?”

If you’re thinking about googling “the best places to see fall colours near Toronto,” you can wonder no more. Uxbridge is the best place around to see fall foliage. For skating enthusiasts, check out the Uxbridge Arena public skating, and lace up because the rink is now open.

As always, Uxbridge is a fantastic place to live and visit all year long, and fall really is a season to celebrate. We hope to see you soon at one of these long-awaited and much-enjoyed events.

Are you in the market for a new home and want to explore your options in more detail? Our Uxbridge real estate agents are happy to help with anything you need. Contact us today at Cindy@Cindywood.ca or call 905.852.6143 to get started.

Book a Consultation

Whether you are buying or selling, our team is here to help make the most of your next move.

Get in Touch

Get Market Updates

Join our newsletter to know when the newest listings hit the market, and get expert real estate advice to inform your next move.