Holiday in the Highlands
2025 Schedule
November 17 - December 21
Elf on a Shelf Hunt
When you shop local this holiday season you’ll have an opportunity to spot our South Grey Chamber of Commerce Elf on Shelf. These elves are working in our local shops, and when you spot one working, we encourage you to take their photo, post it on your social media, tag @southgreychamberofcommerce for your chance to win a holiday prize pack. #ElfOnTheShelfHighlands
November 28 - December 19
Deck the Highlands
The Deck the Highlands Contest invites residents and businesses in Grey Highlands to showcase their holiday spirit by spectacularly decorating their properties. The event is a lighthearted competition that aims to boost community pride, encourage local engagement, and create a beautiful, festive atmosphere throughout the towns and villages. Registration for the contest closes November 20. #DeckTheHighlands
November 22
The Hanley Institute Christmas Market
9 am - 1pm @ The Hanley Institute
The Hanley Institute Christmas Market is an annual event in Flesherton that features handmade products and food created by talented local youth. The Hanley Institute, which is a non-profit organization focused on youth, hosts the market to provide a platform for young entrepreneurs to sell their wonderful goods. #ShopLocalHolidays
Holiday Tree Lighting
5pm - 6pm @ Flesherton Library
Special guest Mrs. Claus will be on hand to light up the Grey Highlands holiday tree. We’ll be serving hot cocoa to keep everyone warm, and music will be performed by Larry and Cowboy Up. Start your holiday countdown with our joyous tree lighting ceremony. #HolidayInTheHighlands
Free Frosty Skate
7pm - 830pm @ Flesherton Arena
Grab your family, friends, and your warmest winter gear, and join us for the Free Frosty Skate at the Flesherton Arena! This is your chance to glide and celebrate as part of the annual Holiday in the Highlands festivities. After the tree lighting and hot chocolate at the Kinplex, head over to the arena to lace up for a night of free festive fun on the ice! #FamilyHolidayFun
November 28
Chili
5:30 - Until Sold Out @ Scoop Me Up
Warm yourself up with chili and good friends at South Grey Chamber of Commerce 2025 new business of the year Scoop Me Up. Then head over to the Santa Claus parade. #MarkdaleOntario
Markdale Santa Claus Parade
6:30pm - 8:00pm @ Main Street Markdale
The Markdale Santa Claus Parade is a community event featuring festive floats from local businesses and organizations, which travels through downtown Markdale on Main Street. Register your float by Wednesday, November 25 to be included in this year’s parade. #SmallTownChristmas #MarkdaleSantaParade
November 29
Holiday Market
9:00am - 2:00pm @ Flesherton Kinplex
The Flesherton and District Farmers' Market Christmas Market is a special, indoor extension of the regular seasonal farmers' market, transitioning from its summer outdoor location to the cozy confines of the Flesherton Kinplex for the holidays. Shop local, shop Canadian, support your friends and neighbors. #ShopLocalHolidays
Santa's Workshop
1:00pm - 4:00pm @ Annesley Church Markdale
The Santa's Workshop at Annesley Church offers a dedicated space for children to engage in hands-on, festive activities that capture the magic of Christmas. A family-friendly activity center where children can get creative and immerse themselves in the spirit of the North Pole by decorating cookies supplied by Markdale Recreation Committee, crafting their own ornament, and having their photo taken with Santa and Mrs. Claus, sponsored by Sea and Ski Realty. Pre-registration for the Santa and Mrs Claus photos is required. #FamilyHolidayFun #SmallTownChristmas
Paige Warner
7:00pm - 9:00pm @ Annesley Church Markdale
Holiday in the Highlands concludes with a gorgeous holiday concert by alt-pop, soul, singer/songwriter Paige Warner. #HolidayInTheHighlands