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Trip Ideas

Hiking on Caledon trails in winter

Rediscover Winter

Let the rolling hills of Caledon transport you to a gorgeous winter playground in the countryside. Caledon is one of the GTA's best kept secrets; a rural escape that's so close to the city but a world away. Come and discover Caledon's cross-country trails for skiing, snowshoeing and more, plus great local restaurants and charming accommodation for the perfect winter staycation.    


When the white stuff falls, it's time to get out and play. And trust us – we get a lot of snow up here in the hills! There are so many ways to get outside and enjoy winter in Caledon. Imagine saddling up in the crisp morning air for a horseback trail ride at Teen Ranch, or strapping on snowshoes to take a walk through an untouched canopy of snow capped evergreens. 

You could ski for hours in the Albion Hills Conservation Area, with 26km of paths through pristine forests. Terra Cotta Conservation Area also has wide groomed trails suitable for skiers of all ages and abilities. And if you want to go the distance, Caledon boasts two rail trails – the Caledon Trailway and the Elora Cataract Trailway – which follow the lines of abandoned train tracks that once connected these small towns. 

Mountain bike cycling on trails

Ever heard of biking in the winter? Fat Tire Bikes, as the name implies, have huge tires for riding over snow and are a really unique winter sport. Kick sledding is an amazing workout, whether you're by yourself or if you've got a tiny passenger sitting up front enjoying the ride. You can rent all the gear you need, like kicksleds, snowshoes and fat tire bikes, at Caledon's conservation areas, so all you have to do is show up and have fun. 

Click here to view the Caledon Trails page


After enjoying the trails and working up a sweat, it's definitely time for some well deserved Après-SkiCaledon has lots of unique local restaurants, full of authentic small town charm and fantastic food. 

You'll quickly notice that a lot of Caledon eateries are housed in historic buildings that have lovingly preserved their original architecture. The Cheltenham General Store's Cafe is a true blast from the past, dating back to 1887 and full of old time memorabilia.  

The locals are very loyal to Rays 3rd Generation Bakery in Alton, which has excellent gourmet offerings and local Caledon brews on tap. 

You'll need to book ahead if you want a table at the gorgeous Spirit Tree Estate Cidery, where you can try their homemade cider while enjoying wood-fired pizza, appetizers and mouth watering mains. 

Or perhaps you've already seen the pictures of Headwaters Restaurant which overlooks a stunning rushing waterfall. It is indeed as beautiful as it looks, but if you want to sit in the iconic glass room that overlooks the water, be sure to call and reserve ahead of time. 

Click here to view some of Caledon's dining experiences. 


Caledon is the perfect place for a quick weekend trip or a mini staycation, especially if you're coming to enjoy winter activities. Charming inns and quaint B&Bs nestled in the lush countryside are a wonderful escape, with a slower pace of life, beautiful scenery, and friendly locals. 

For something truly adventurous, you must try glamping at Alabaster Acres – yes, even in the winter! You'll sleep in luxurious heated tents in the woods and wake up surrounded by pure nature.  

Small inns like the Forks of the Credit Inn or Inn on the Moraine are the perfect place to unwind and truly enjoy the peace and quiet of Caledon's countryside. 

If you're looking to splurge, pamper yourself at the historic Millcroft Inn and Spa, which has gorgeous grounds along a rushing river. Be sure to also check out the Alton Mill Arts Centre around the corner. 

Click here to view some of Caledon's places to stay.

Forget the long drives. Escape the crowds. Skip the long lines. Come out and play this winter in Caledon, and discover the charms that await you in the GTA's backyard. 

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