248379 Side Rd. 5, Orangeville
Posted on January 8, 2021 / 6225
Listing Type : Cross Country Ski / Snowshoe
Location : Central Ontario
Note : NEW Trail
X-Ski km : 14
Skate km : none
Snowshoe km : 8
Skill Level : Intermediate, Advanced
Terrain : large hills, narrow paths, steep sections, tight turns, open fields, flat sections
Facilities : parking, lodging near, food close by, trailhead map, good trail signage, trails maintained, track set
Trail Fee : Free

Length –  14 km

Cross Country track set   –  14 km
Skate Skiing  groomed  –  none
Snowshoe  trail  ~ 8 km 

Skill – best for Intermediate/ Advanced users

Terrain –  flat open field and orchards, woodlots, rolling hills, a few  tight turns, steep climbs and fast long descents

Hours –  Daylight hours

Fee – Free

Trail Map – Gate map board, adequate signage, yellow diamond markers

Facilities – A parking lot that‘s it, a rustic experience, pack what you need. Orangeville is the closest large town.

Highlights – Scenic, wilderness, quite, equally good for either sport

Phone – None

Website – Hockleycrest Ski Trails,  Caledon Hills  Club

 Current Conditions – frequent blog posts

Similar Trails –  Wasaga, Glenelg, Mono Nordic

Local Clubs – Mono Nordic, Halton Outdoor Club

Access – Limited parking at the south lot at 248379 Side Road 5, east of Airport Rd. Hwy 18

Street parking at the Bruce Trail north exit 933536 Airport Rd.


No Fatbikes Please

At the end of last season, I discovered Hockleycrest, a wonderful Nordic ski and Snowshoe trail network with great paths and marvellous scenery. 

This new location close to Toronto, which few of you know of, is just east of Orangeville. Unique in its existence and surroundings, and highly recommended.

Apparently, these 14 km loops (about 8 km for Snowshoeing) have only been available for about 5 years. Using existing Bruce Trail conservation lands and private lots this trail system is a joy to traverse.

Equally suitable for a day of some fine Classic Cross-country Skiing or to Snowshoe, my comments here apply to both sports. Unfortunately, leave your skate skis at home there is no space to glide.

Hockleycrest as a whole is best suited for seasoned Intermediate/ Advanced users. I would not suggest beginners start learning here. The paths are not always wide enough to maneuver or bail when you are about to fall. 

Though there is a fair amount of flat open terrain to cover, there are moments along the paths that can have tight turns with fast downhills into valleys and substantial climbs. More so the further in you go. 

Made up of many short loops, this gives you route options but also may have you reaching for a map every ten minutes. 

My wife trekked along the Snowshoe paths and was delighted at the variety of scenery she encountered as I was skiing with my son. Usually, trails wander through the forest, but here they also open up to orchards, farm fields, pasture land and big sky panoramas. 

You may spot on your journey a Taoist Tai Chi centre and a Christian retreat all in harmony with the serene, quiet beauty of your surroundings.

There are a sufficient amount of numbered signs to guide you. Little of the trails marked are shared so Snowshoeing takes you elsewhere.  The main entrance, with parking, is on the south end.

A big thanks to David a local resident. This has been his pet project along with others to make Hockleycrest available to the public, for free! He grooms and sets the ski tracks regularly plus posts daily snow reports on his blog.  Wow!

See fit to donate a few bucks to pay for his gas or support the Bruce Trail organization. It would be awesome if this location became a permanent choice for us to escape to.

I am so glad a fellow skier mentioned this place in an email. Just 30 minutes north of Brampton, it’s so close, just pray for snow and get out there soon, you’ll love it.

Opening Hours
  • Monday :Daylight Hours
  • Tuesday :Daylight Hours
  • Wednesday :Daylight Hours
  • Thursday :Daylight Hours
  • Friday :Daylight Hours
  • Saturday :Daylight Hours
  • Sunday :Daylight Hours
Hockleycrest ski trail map

Hockleycrest ski trail map


Hockleycrest Snowshoe trail map

Hockleycrest Snowshoe trail map

Total Score 6 REVIEWS
Fun Factor: Scenic: Trail Design: Technical: Workout:
Leave a review
Fun Factor: Scenic: Trail Design: Technical: Workout: