Holiday in the Highlands 2025:
A Guide to Festive Fun in Grey Highlands
The holiday season in Grey Highlands is full of excitement, community spirit, and festive celebrations. From mid-November through December, towns and villages come alive with special events that bring families, friends, and neighbours together. Here’s a guide to everything happening during Holiday in the Highlands 2025.
Elf on a Shelf Hunt | November 17 – December 21
Discover the magic of the season while shopping local with the Elf on a Shelf Hunt. Hidden throughout participating businesses, these mischievous elves are spreading holiday cheer and looking for curious eyes to spot them. Snap a photo when you find one and share it on social media with the South Grey Chamber of Commerce or Explore South Grey tagged for a chance to win a festive prize pack. It’s a fun way to explore local shops and get into the holiday spirit.
Deck the Highlands Contest | November 28 – December 19
Residents and businesses throughout Grey Highlands are invited to showcase their holiday creativity in the Deck the Highlands contest. This friendly competition encourages everyone to decorate their homes and storefronts, transforming the community into a sparkling winter wonderland. Registration closes on November 20, giving everyone plenty of time to plan their festive displays.
The Hanley Institute Christmas Market | November 22, 9:00 AM – 1:00 PM
Flesherton’s Hanley Institute Christmas Market is a celebration of local talent and youth entrepreneurship. Visitors can browse handmade products, delicious treats, and unique gifts crafted by young creators in the community. The market provides a wonderful opportunity to support local youth while finding special gifts for the holidays.
Holiday Tree Lighting | November 22, 5:00 PM – 6:00 PM
Kick off the season with the annual Grey Highlands holiday tree lighting at the Markdale Library. Special guest Mrs. Claus will help illuminate the town’s Christmas tree as festive music is performed by Larry and Cowboy Up. Hot cocoa will be served, creating a warm and cheerful atmosphere for families and friends to gather and celebrate together.
Free Frosty Skate | November 22, 7:00 PM – 8:30 PM
Continue the festive fun at the Flesherton Arena with the Free Frosty Skate. Bundle up and enjoy gliding across the ice with loved ones in this family-friendly celebration. It’s the perfect way to keep the holiday spirit alive after the tree lighting ceremony and a cozy cup of hot chocolate.
Chili at Scoop Me Up | November 28, 5:30 PM – Until Sold Out
Warm up before the Markdale Santa Claus Parade with a hearty bowl of chili at Scoop Me Up, recently recognized as South Grey Chamber of Commerce’s 2025 New Business of the Year. Enjoy delicious food and community camaraderie before heading out to the parade.
Markdale Santa Claus Parade | November 28, 6:30 PM – 8:00 PM
The Markdale Santa Claus Parade is a festive highlight of the season, featuring vibrant floats from local businesses and organizations. The parade travels through downtown Markdale along Main Street, bringing the community together to celebrate the holidays in true small-town style. Float registration closes on Wednesday, November 25 for those wishing to participate.
Holiday Market at Flesherton Kinplex | November 29, 9:00 AM – 2:00 PM
The Flesherton and District Farmers' Market transforms for the holidays with a special indoor market at the Kinplex. Local vendors offer a wide variety of gifts, crafts, and treats, making it a perfect destination to shop local and support your community during the holiday season.
Santa's Workshop | November 29, 1:00 PM – 4:00 PM
Families can enjoy a hands-on holiday experience at Santa's Workshop at Annesley Church in Markdale. Children can decorate cookies, make their own ornaments, and get their photos taken with Santa and Mrs. Claus. Pre-registration is required for photos, and the workshop offers a festive, interactive way for kids to immerse themselves in the magic of the North Pole.
Paige Warner Holiday Concert | November 29, 7:00 PM – 9:00 PM
The celebration concludes with an intimate holiday concert featuring alt-pop and soul singer-songwriter Paige Warner. Enjoy a night of music that captures the warmth and spirit of the season, providing a perfect ending to a weekend full of festive events.
Celebrate the season in Grey Highlands and experience the joy, community, and magic of the holidays. For more details and to view the full Holiday in the Highlands schedule, visit the official event page: Holiday in the Highlands 2025