Winter

Wander-Land

Downtown Stratford's Annual Winter Wander-Land is Back!

November 29 & 30, 2025 | 11AM - 5PM

We’re ready for a full weekend of festive fun as we kick off the holiday season with your all-time favourite traditions and some exciting new additions!

Prepare for the enchanting Polar Express Train around City Hall, Festive Photo Backdrop for magical holiday pics, Yuletide Cabins and Food Trucks at our charming Winter Food Market, crackling Fire Pits for roasting Rice Krispie Treats, Santa Claus “coming to town,” DJ Ethan Maac and Roaming Carollers to fill the air with festive tunes, Horse and Wagon Rides from Memorial Gardens, Christmas Tree Market by B&C Custom Landscaping for the perfect tree to take home, and Live Music from Retro Resonance on York St Saturday evening!  If it’s frosty outside, check out the Cultural Crafts for kids in Stratford Tourism or participate in a fun Scavenger Hunt at the Library!

Come get into the festive spirit with family fun in Market Square and York Street. ✨🎅✨

* Artwork by George Burkholder

Highlights of the season.

Winter Wanderland Passport

All Weekend

Polar Express Train Rides

11am - 5pm

Cozy Fires & Treats

11am - 5pm

CHRISTMAS TREE Market

11am - 5pm

Cultural Crafts for Kids

11am - 5pm

Winter Scavenger Hunt

11am - 5pm

Strolling Holiday CAROLLERS

12pm - 4pm

Selfie With an Elfie!

12pm - 4pm

Here Comes Santa Claus

12pm - 4pm

Horse & Wagon Rides

12pm - 4pm

Yuletide Cabins & Food Trucks

11am - 5pm

Live Music! Retro Resonance

Sat. 5pm - 8pm

Winter Food Market

Yuletide Cabins &
Festive Food Trucks

We are so delighted to bring you even more reasons to hang out at the square all weekend.

Our Yuletide Cabins and Festive Food Trucks will be sprinkled throughout the square offering delicious fare, warm drinks, and even some “adult” drinks through the al fresco program.

Yuletide Market Huts

Festive Food Trucks

  • Ken’s Fries 
  • Features serving their fall-apart smoky turkey legs, brisket burnt ends, candy-apple pork belly, loaded brisket poutine, smoked shotgun shells⁠

Shop, Dine & WIN with our Winter Wander-Land Passport!

WIN BIG: $250, $150, or $100 in Downtown Dollars!

One of the MOST EXCITING FEATURES of the year is our Winter Wander-land Passport – which starts November 22nd and runs until December 23rd. This features a whopping number of downtown businesses that offer a validation sticker when you shop, dine or use services. Collect 8 stickers and enter to win one of 3 Downtown Dollar prizes! WOW!!!! You must purchase something from each location however there there is no minimum cost.

Pick up your Passport at 47 Downie Street or at participating local businesses. Bring completed Passports back to 47 Downie Street by Monday, December 23rd at 5pm.

Draw will occur on December 23rd at 6pm. Winners will contacted directly.

We thank our Sponsors – GOOD VIBRATIONS ROCK SHOP and RHEO THOMPSON CANDIES!