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Trip Ideas

A band dressed as Santa Claus marches in a parade

Light Up Caledon

The days may be growing shorter, but there is plenty happening throughout the town to brighten up the dark, snowy evenings as we head into the holiday season. Gather with family, friends, and neighbours to celebrate and make memories at parades, tree lightings, and markets across Caledon.  


Downtown Bolton Christmas Market

Friday, December 2, 6:00 PM

Downtown Bolton  

Join us for our second annual ‘Ye Olde Tyme Christmas’ in downtown Bolton, featuring a giant snow globe, free photos with Santa, carolers, food trucks, and over 50 market vendors on Queen St in the downtown core.

Cheltenham ‘Light up the Night’ Parade

Friday, December 2, 7:00 PM

Cheltenham

Bolton Kin Santa Claus Parade

Saturday, December 3, 11:00 AM

Downtown Bolton

Caledon Village Parade & Tree Lighting

Saturday, December 3, 4:30 PM

Caledon Village (beginning at the public school)

Palgrave Rotary Tree Lighting Event

Saturday, December 3, 5:30 PM

Stationlands Park (across from Fire Station)

This annual Palgrave Rotary event features a number of activities throughout the evening, including tree lighting, singers, hot chocolate, a visit from Santa, and the announcement of the home decorating winner. Visit Just Sayin’ Caledon for more specific event times and more information.

Valleywood Tree Lighting

Saturday. December 3, 6:00 PM

Valleywood Fire Station 307


Jinglewood Tree Lighting

Sunday, December 4, 7:00 PM

Inglewood Stationlands

Caledon East Tree Lighting Event

Wednesday, December 14

Caledon Town Hall

Take photos with Santa and Mrs. Claus, warm up with hot chocolate, and enjoy some festive music at this tree-lighting event in Caledon East. Donations of non-perishable items are welcomed!

Terra Cotta Holiday Event

Sunday, December 18, 3:00 - 4:00 PM

Terra Cotta Community Centre

All are welcome to gather and enjoy hot chocolate and other goodies while celebrating the holiday season together.

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