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Monthly Message: Downtown Orangeville gears up for back-to-back holiday celebrations

November 3, 2025   ·   0 Comments

Downtown Orangeville is set to sparkle brighter than ever this year with the return — and expansion — of the Joy + Lights Festival, a two-weekend celebration that brings the magic of the holiday season to life with twinkling lights, live entertainment, artisan shopping, family fun, and the unmistakable warmth of community spirit.

Whether you’re a longtime local or visiting for the first time, the Joy + Lights Festival offers the perfect opportunity to step into a storybook setting filled with the sights, sounds, and flavours of the holidays.

The first weekend is Merry & Bright and creates a scene straight out of a Hallmark movie at The Very Merry Holiday Market on Second Street, Nov. 21 to 23 and Nov. 28 to 30. This open-air, European-style Christmas market transforms Second Street into a sparkling winter wonderland lined with wooden vendor stalls, glowing garlands, and a magnificent holiday tree.

Browse a curated selection of handcrafted, one-of-a-kind gifts and decorations from talented local artisans, sample mouthwatering seasonal treats, and enjoy live entertainment that fills the streets with festive cheer.

Warm up at the Fireside Sips Lounge, where you can enjoy mulled wine and craft beer, or simply stroll through the glowing market with a hot cocoa in hand as the lights twinkle overhead. You may even be lucky enough to catch a gentle sprinkle of snow — the perfect finishing touch to a truly magical experience.

And don’t forget to explore the downtown shops and cozy cafés that make Orangeville such a special destination. During the festival, you’ll earn DOUBLE Joy Book stamps on your purchases at downtown shops — an extra reason to shop, savour, and soak up the spirit of the season.

Kick off the holiday season in true Orangeville style on Friday, Nov. 21, with the Annual Tree Lighting and Starlight Shopping night — a cherished local tradition that glows brighter every year.

The evening begins with live music and strolling light shows, followed by David Nairn’s beloved reading of ’Twas the Night Before Christmas — a heartwarming moment that perfectly captures the nostalgia of the holidays. As the clock ticks closer to the main event, gather around with friends and family for the Tree Lighting Ceremony, featuring Santa and special guests.

After the tree is lit, Santa will stay to greet visitors on Mill Street while you wander through downtown’s beautifully decorated streets. Enjoy festive caroling, peek into elaborately dressed shop windows, and make a dent in your holiday shopping list. Participating stores will be open late — and offering DOUBLE Joy Book stamps to make the evening even more rewarding.

Santa Claus is coming to town — and he’s taking over Broadway!  On Saturday, November 22nd, the Town of Orangeville’s annual Santa Claus Parade, one of the most anticipated events of the season, will light up Broadway with dazzling floats, joyful characters, and of course, the jolly man in red himself.

Arrive early to catch pre-parade entertainment on Broadway, explore the shops, and grab your favourite festive treat before the parade begins. Whether you’re young or just young at heart, this magical parade is a must-see highlight of the Joy + Lights Festival.

The festival’s second weekend turns up the sparkle with Firelight & Frost — a dazzling blend of warmth and wonder.

Enjoy free skating all weekend on Mill Street’s all-season synthetic rink surrounded by glowing lights, festive music, and cozy fireside seating. Watch a mesmerizing fire show, marvel at ice-sculpture carvings, and enjoy family-friendly activities that will keep your spirits high.

Of course, Santa will make a few more appearances — along with the return of the Very Merry Holiday Market on Second Street. With festive flavours, local shopping, and cozy eateries just steps away, Firelight & Frost is the perfect way to wrap yourself in the magic of the season.

This November, Downtown Orangeville invites you to gather your loved ones, bundle up, and experience two weekends of holiday cheer, local charm, and unforgettable memories.

Don’t miss a moment of the magic — visit DowntownOrangeville.ca for full event details and schedules because when it comes to celebrating the season, Downtown Orangeville truly shines brightest at Joy + Lights.

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