Jockey Hill and Wintergreen Ridge Trail
Jockey Hill and Wintergreen Ridge Trail
3.1
(23)
88
hikers
Jockey Hill and Wintergreen Ridge Trail
01:41
6.14km
90m
Hiking
Embark on an easy hike along the Jockey Hill and Wintergreen Ridge Trail, a peaceful route spanning 3.8 miles (6.1 km). You will experience a gentle ascent, gaining 305 feet (93 metres) in elevation over approximately 1 hour and 40 minutes. The path winds through pleasant long-needle pine forests, offering…
Last updated: April 23, 2026
Tips
Your route passes through protected areas
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Waypoints
Start point
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13 m
Jockey Hill–Wintergreen Parking Area
Highlight • Parking
There are multiple mountain biking and hiking trails here, of varying levels of difficulty.
Tip by
6.14 km
End point
Way Types & Surfaces
Way Types
4.47 km
1.66 km
< 100 m
Surfaces
4.44 km
1.68 km
< 100 m
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Elevation
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Weather
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Today
Saturday 30 May
16°C
8°C
39 %
Additional weather tips
Max wind speed: 22.0 km/h
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This route was planned by komoot.
Frequently Asked Questions
Where can I park for the Jockey Hill and Wintergreen Ridge Trail?
Parking is available at the Jockey Hill–Wintergreen Parking Area. Keep in mind that this parking area is not plowed during the winter months.
Is the Jockey Hill and Wintergreen Ridge Trail suitable for beginners?
Yes, the trail is generally considered easy and is well-suited for beginners. While there's a slow but steady uphill climb for the initial third, the overall difficulty is rated as 'Easy'.
Is the trail a loop or an out-and-back route?
The Wintergreen Trail section of this route is a loop, offering a varied experience without retracing your steps.
What is the terrain like on the trail?
The terrain is diverse. You'll encounter a slow but steady uphill climb initially, followed by a downhill section. The path winds through pleasant long-needle pine forests with smooth sections, and the overall 1-3/4 miles ascending and traversing Jockey Hill present interesting and varied ground.
What natural features can I see along the route?
You can expect varied scenery, including pleasant long-needle pine forests. Notable natural elements include several waterfalls, with a larger one visible further down the trail, and small creeks that add to the natural beauty.
When is the best time of year to hike this trail?
The trail can be enjoyed in multiple seasons. However, it's important to note that the parking area is not plowed in winter, which might affect access. Spring, summer, and fall offer excellent conditions for hiking.
Is the Jockey Hill and Wintergreen Ridge Trail dog-friendly?
Yes, dogs are generally permitted on trails within the Bluestone Wild Forest. Please ensure your dog is kept on a leash and that you clean up after them to preserve the natural environment for everyone.
Do I need a permit or pay an entrance fee to access the Bluestone Wild Forest?
No, there are typically no permits or entrance fees required to access the Bluestone Wild Forest or its trails, including the Jockey Hill and Wintergreen Ridge Trail. It's a public wild forest area.
Does the trail connect to other paths in the area?
Yes, the Jockey Hill and Wintergreen Ridge Trail is part of the extensive Bluestone Wild Forest trail system. It connects to other trails like the Mushroom, Skull, Wood Road, Cap, and Old Mushroom Exit trails, allowing for longer and more varied excursions.
What activities are allowed on the trail besides hiking?
Beyond hiking, the trail is suitable for various other activities depending on the season. These include mountain biking, skiing, snowmobiling, and snowshoeing, making it a versatile outdoor destination.