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Routes
Hiking trails & Routes
United States
Vermont
Windham County

Pinnacle at Windmill Hill Loop

Easy

4.9

(4809)

12,182

hikers

Pinnacle at Windmill Hill Loop

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

A

Start point

Parking

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1

2.21 km

Windmill Mountain

Highlight • Summit

B

5.63 km

End point

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Way Types & Surfaces

Way Types

5.63 km

Surfaces

5.59 km

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Elevation

Elevation

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Weather

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Today

Friday 8 May

14°C

-1°C

23 %

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Max wind speed: 20.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How long does it typically take to hike the Pinnacle at Windmill Hill Loop?

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.

Where is the trailhead for this loop, and is there parking available?

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.

Is the Pinnacle at Windmill Hill Loop suitable for beginners?

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.

What is the terrain like on this trail?

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.

What can I see along the route?

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.

Does this trail connect with other paths?

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.

Is the Pinnacle at Windmill Hill Loop dog-friendly?

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.

What is the best time of year to hike this trail?

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.

Are there any permits or entrance fees required for this trail?

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.

How well-marked is the trail?

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.

What should I bring for a hike on this loop?

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.

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