Your new favourite holiday tradition is just 45 minutes from the GTA

Aerial view of a historic downtown in the fall

Looking to swap the city’s hustle for something a little more storybook-worthy this holiday season?

Just under an hour from the GTA, Orangeville is transforming into a twinkling holiday haven, where Victorian storefronts glow under string lights and the scent of hot chocolate fills the air. Think vintage charm, Euro-style markets, and all the festive touches that make small-town Christmas feel like a well-kept secret...until now.

From late November through December, Orangeville offers a full calendar of events that feel both intimate and indulgent. Whether you're on the hunt for handcrafted gifts or simply want to bask in the nostalgia of an old-fashioned holiday, this town is pulling out all the stops.

Two weekends of wonder

Mark your calendar: Orangeville is officially setting the seasonal tone with a dazzling start to the holiday season. From al fresco markets to tree lightings and twinkling streetscapes, it’s a charming kickoff you’ll want to return to year after year.

Holiday gift market (November 21 to 23 and 28 to 30)

Orangeville’s holiday gift market brings together local artisans, hand-crafted gifts, and the unmistakable ambiance of a European Christmas market. Roam through snow-dusted booths, sip something warm, and find thoughtful treasures that actually feel… well, thoughtful.

Joy and lights tree lighting (November 21)

If there were ever a night to lean into the magic, this is it. Watch as Santa himself lights up the town tree, then follow the glow down Broadway, where window displays glisten, carolers sing, and holiday charm hangs thick in the air.

Santa Claus parade (November 22)

A classic with a twist of Orangeville charm. Expect whimsical floats, beloved characters, and that contagious joy that only comes when the big guy in red rolls through town. Come early for hot cocoa and a stroll. Every window feels like a snow globe brought to life.

Skate on Mill Street (November 28 to 30)

Lace up your skates as historic Mill Street becomes a picture-perfect pop-up rink with rentals, lights, and classic holiday music. Whether you're gliding gracefully or clutching the boards with glee, it’s pure holiday romance.

Rapunzel: A Braid New World

November 27 to December 21

A hilarious, high-energy panto live at the historic Orangeville Opera House! Packed with music, dancing, laughs and 100% Canadian hair products! Get your tickets now... it's ‘hair’ today, gone tomorrow!

Christmas in the Park

Nightly in December

Every evening, Kay Cee Gardens transforms into a mesmerizing holiday wonderland. Millions of lights. Whimsical scenes. A gentle soundtrack of seasonal classics. It’s both a family tradition and a serene escape. It's a place to walk slowly, breathe deeply, and feel the meaning of the season.

Whether you're seeking an enchanting day trip or the perfect winter weekend, Orangeville is proving that sometimes the best seasonal escapes aren’t far from home. They’re just up the road, wrapped in twinkling lights and tied with a velvet bow.

Insider Tip: Stay for the weekend and explore local cafés, bakeries, and boutiques, all decked in their holiday best. It’s the kind of town that makes you want to linger a little longer.

Visit LoveOrangeville.ca to plan your visit.

0 Likes