Holiday in the Highlands 2026: A Festive Weekend Guide to Flesherton & Markdale, Ontario

A tree lighting, a free skate, a small-town Santa Claus parade, and a market full of local makers — South Grey's holiday kickoff, in one weekend.

Quick Answer

Holiday in the Highlands is the annual holiday festival in Grey Highlands, Ontario, held in late November. It includes a tree lighting and free skate in Flesherton, the Markdale Santa Claus Parade along Main Street, a Santa Workshop and holiday market, and a holiday concert in Markdale. Events are free or low-cost and family-friendly.

What Is Holiday in the Highlands?

Holiday in the Highlands is Grey Highlands' signature kickoff to the holiday season, a series of community events across Flesherton and Markdale. It brings together local businesses, volunteers, and families, and the Markdale Santa Claus Parade at its centre is organized by the South Grey Chamber of Commerce with the Municipality of Grey Highlands.

Flesherton: Tree Lighting and Free Frosty Skate(November 21st)

The festivities kick off in Flesherton, where Mrs. Claus lights the Grey Highlands holiday tree outside the library. Warm up with hot chocolate at the Kinplex, then lace up for a free skate on the arena ice, one of the most relaxed, genuinely community-minded evenings of the season.

Holiday tree lighting in Flesherton, Grey Highlands, Ontario

Markdale: The Santa Claus Parade(November 27th)

The Markdale Santa Claus Parade rolls down Main Street with festive floats from local businesses and community groups, music, and a grand finale with Santa himself. It's free, it's full of neighbours, and it draws families from across South Grey.

Local business float in the Markdale Santa Claus Parade

Santa's Workshop and Holiday Market(November 28th)

The next day brings Santa's Workshop and a holiday market, a good place to find locally made gifts while keeping dollars in the community. Bring cash for smaller vendors and arrive early for the best selection.

Make It a Full Weekend: Add a Winter Waterfall Walk

If you're staying through Sunday, Hoggs Falls near Flesherton stays accessible through the winter and is a beautiful, quiet walk when the falls start to ice up. Wear spikes or good traction, since the trail can be slick.

Hoggs Falls near Flesherton in winter

Planning Tips

  • Dress for standing outdoors: layers, hats, and warm boots for the parade.

  • Arrive early for parking; Main Street fills up on parade night.

  • Check exploresouthgrey.ca for 2026 updates before you travel.

  • Bring a small donation for local food drives if you can; South Grey's community food banks are busiest in winter.

  • Shop local: independent shops in Flesherton and Markdale are the heart of the holiday season here.

Frequently Asked Questions

  • Holiday in the Highlands is typically held in the second half of November. [CONFIRM 2026: expected tree lighting the Saturday before the parade, with the Markdale Santa Claus Parade on Friday, November 27.]

  • The tree lighting, free Frosty Skate, and Santa Claus Parade are free to attend. Check individual events, like concerts, for ticket details.

  • The parade travels along Main Street in downtown Markdale, in the Municipality of Grey Highlands, Ontario.

  • Yes. The parade is organized by the South Grey Chamber of Commerce, and local businesses and organizations are invited to register a float in advance through the Chamber's website. [CONFIRM link and deadline.]

  • Yes. The tree lighting, free skate, parade, and Santa's Workshop are designed for families, and the events are short enough for little ones. Dress warmly and bring a sled or wagon for toddlers.

  • Flesherton and Markdale both have local cafés and restaurants, and exploresouthgrey.ca lists nearby places to eat and stay. [Add direct links to your member directory.]