4.9
(4809)
12,182
hikers
01:38
5.63km
160m
Hiking
Discover the natural beauty of the Pinnacle at Windmill Hill Loop, an easy hiking trail that offers a diverse landscape. This route covers 3.5 miles (5.6 km) with an elevation gain of 529 feet (161 metres), typically taking about 1 hour and 37 minutes to complete. As you hike, you…
Last updated: April 23, 2026
Waypoints
Way Types & Surfaces
Way Types
5.63 km
Surfaces
5.59 km
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Friday 8 May
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23 %
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This route was planned by komoot.
The loop is approximately 5.6 kilometers (3.5 miles) long and generally takes about 1 hour and 40 minutes to complete. This duration can vary based on your pace and how often you stop to enjoy the scenery.
The trail is part of the Windmill Hill Ridgeline Trail System in Westminster, Vermont. A distinctive starting point for some routes is the Pinnacle Trailhead, which is marked by an old, ornate metal gate. Parking is typically available at designated trailheads within the system.
The loop is rated as 'easy' overall, but sections can be moderately challenging. The climb along the Holden Trail is gentle, while parts of the Headwaters Trail involve a moderate ascent. You might encounter occasionally rugged terrain with short, steep sections and easy-to-navigate rock ledge scrambles. It's a good option for those with some hiking experience or beginners looking for a bit of a challenge.
The trail offers varied terrain, including wide and narrow paths. You'll traverse exposed bedrock outcrops, wind through woodlands, and cross a small stream on stones. The route passes through stands of large oak and ash trees, 'savannah-like woodland,' attractive fern glades, and rugged rock outcrop ledges.
As you hike, you'll encounter diverse natural features like fern glades, rugged rock outcrop ledges, and old stone walls. The summit of The Pinnacle provides open ledges with scenic views. You'll also pass by Windmill Mountain.
Yes, the route described as a 'lollipop route' to The Pinnacle combines sections of several primary trails within the Windmill Hill Ridgeline Trail System. These include the red-disc-blazed Holden Trail, the blue-disc-blazed Headwaters Trail, and the white-blazed main Ridgeline Trail.
Yes, dogs are allowed on the trails within the Windmill Hill Ridgeline Trail System. Please ensure they are kept under control, and always clean up after your pet.
The trail system is open year-round, offering different experiences with each season. Spring brings lush greenery, summer offers warm hiking, fall showcases vibrant foliage, and winter provides a serene, snowy landscape. Choose the season that best suits your preferences.
The Windmill Hill Ridgeline Trail System, including this loop, is managed by the Windmill Hill Pinnacle Association. There are no specific permits or entrance fees required to access the trails for public hiking.
The trails within the system are generally well-marked and easy to follow. However, some parts, particularly on the Pinnacle Ridge Trail, can occasionally be harder to discern, so paying attention to trail markers is always recommended.
Given the varied terrain, including potentially rugged sections and stream crossings, sturdy hiking shoes are recommended. Bring water, especially on warmer days, and consider insect repellent. Layered clothing is also advisable due to changing conditions.