Winter

Wander-Land

planning for Downtown Stratford's Annual Winter Wander-Land is underway!

November 28 & 29, 2026 | 11AM - 4PM

We’re getting ready for a full weekend of festive fun to kick off the holiday season with your all-time favourite traditions!

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,”  Roaming Carollers to fill the air with festive song, Horse and Wagon Rides from Memorial Gardens, and Live Music from Amanda & James Country Duo FRIDAY evening and Retro Resonance on SATURDAY evening, both on York Street!  

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 - 4pm

Cozy Fires & Treats

11am - 4pm

CHRISTMAS TREE Market (TBC)

11am - 4pm

Cultural Crafts for Kids

11am - 4pm

Winter Scavenger Hunt (TBC)

11am - 4pm

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 - 4pm

Live Music ON YORK ST

Fri. and 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

  • Curry Zone with their delicious Indian curries, samosas, masala tea⁠
  • Alley Cat Cafe with hot chocolate, cat-themed gifts
  • Remaining Vendors to be confirmed

Festive Food Trucks

  • Chris’s BBQ – 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 21st and runs until December 23rd. Collect 8 stickers and enter to win one of 3 Downtown Dollar prizes! You must purchase something from each location however there there is no minimum cost.  (Participating Businesses List to be available closer to the date.)

Passport will be available for pick up at 47 Downie Street or at participating local businesses. Passports are to be returned to 47 Downie Street by Wednesday, December 23rd at 5pm.

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

We thank our Sponsors for sponsoring for the third year in a row! – GOOD VIBRATIONS ROCK SHOP and RHEO THOMPSON CANDIES!