Our Downtown Stratford Annual WINTER WANDER-LAND is BACK! 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!
Join us Saturday, November 29th and Sunday, November 30th, from 11am-5pm.
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! Come get into the festive spirit with family fun in Market Square and York Street. ✨🎅✨
Event Highlights!
Ride the magical POLAR EXPRESS
Sponsored by ON STAGE DANCE (our main sponsor of the event)
ALL ABOARD!!! We are thrilled to be offering again the Polar Express train into Market Square. This elegant train is battery operated (good for the environment) and trackless, with a locomotive and 4 cars which can seat up to 18 children! We are pleased that this year the train is also accessible to children with special physical needs.
This show stopper provides the best authentic steam train engine experience ever.
A huge thank you to On Stage Dance for being the Train Sponsor of our event for the second year in a row!
Delicious Treats at the FIRE PITS
FIRE PIT #1: Sponsored by Alley Cat Cat Cafe (York Street)
FIRE PIT #2: Sponsored by Shawn Malvern at WK FINANCIAL (Market Street)
Our two cracklin’ fire pit areas are back. Get cozy around them and roast delicious rice krispie treats. Supervised by adult volunteers, come warm up your fingers and toes while the kids walk away with the tastiest of treats to fuel their train riding. (Pick up your treats at the Info Huts at both Market Square and York St.)
Strolling Holiday CAROLLERS
Sponsored by KDB Law
We’re delighted to welcome the Victorian Christmas Carollers. Bringing their musical magic to the streets of downtown… gracing us with their enchanting melodies on our Winter Wander-land Weekend. Prepare to listen or sing along to some of the most cherished holiday classics as they weave through the streets of downtown.
CHRISTMAS TREE Market
THE PERFECT weekend to grab your Christmas Tree and Holiday Greenery! Trees are available at both Market Square and on York Street, whichever is more convenient for you. Bring the sweet fragrance of Christmas into your home with fresh Balsam or Fraser Fir trees.
SANTA is coming (back) to town
Sponsored by SUTTON GROUP
Here comes Santa Clause… 🎵 Here comes Santa Claus 🎵… right down Santa Claus lane… 🎵
Santa is setting up shop on his red reindeer sleigh both Saturday and Sunday from Noon to 4pm in Market Square to welcome all the kiddos thoughout the Winter Wander-land weekend . Get your cameras ready as your children (or pets) let Santa know if they’ve been naughty or nice – and what they’re wishing for this year!
Bring your Letters to Santa addressed to: Santa Claus, North Pole, H0H 0H0, Canada and his elves will make sure they get delivered to the North Pole for Santa to read when he gets home.
Thank you to Sutton Group for sponsoring Santa again this year!
Guided Horse & Wagon Rides from Memorial Gardens (next to Pazzo Pizzeria on Ontario St)
We are excited to offer horse-drawn wagon rides this year! Join Dwight, his beautiful horses, and Laurie who will be your tour guide for the ride that winds its way through the historic streets of Downtown Stratford. Starting from Memorial Gardens, located next to 70 Ontario St, rides will take about 20 minutes and will run every half hour on the half hour. You’ll stay nice and warm under the heat lamp while you wait your turn!
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.
The following are confirmed Yuletide Market Huts:
- Curry Zone with their delicious Indian curries, samosas, masala tea
- Alley Cat Cafe with hot chocolate, maybe some kitties?
- B&C Custom Landscaping with Fresh Christmas Trees, wreaths and garlands
- Got It Made with an eclectic mix of handmade and vintage gifts from artisans in the area
- Chocolate Barr’s Candies with a yummy assortment of festive treats and gifts
- Little Green Grocery offering edible goodies and unique gift ideas
And our Festive Food Trucks are:
- Bru Garden with smash burgers and fries, sausage on a bun, hot dogs, poutine, pulled pork
- Features serving their fall-apart smoky turkey legs, brisket burnt ends, candy-apple pork belly, loaded brisket poutine, smoked shotgun shells
Al Fresco Program
A delightful addition to our Winter Food Market includes the chance to drink take-out alcohol beverages (including wines, craft beers and drinks) along with your delicious Yuletide Cabin grub inside the Market Square area.
The Stratford Al Fresco outdoor dining experience has expanded again, so you can dine outdoors with delicious takeout and accompanying drinks from participating Stratford restaurants (see map for locations and window cling to look for below while in the city).
Winter Wander-land is NOT just for families. All ages can enjoy a break here as they head out on their holiday shopping adventure.
Shop, Dine & WIN with our Winter Wander-land PASSPORT
We thank our Sponsors – GOOD VIBRATIONS ROCK SHOP and RHEO THOMPSON CANDIES!
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.
Drop passports off to 47 Downie Street by Monday, December 23rd at 5pm. Draw will occur on December 23rd at 6pm. Winners will contacted directly.
We are truly grateful to the sponsors of Winter Wander-land 2025!
