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Routes
Hiking trails & Routes
United States
Vermont
Addison County
Middlebury

Chipman Hill Loop

Easy

2.8

(25)

52

hikers

Chipman Hill Loop

00:45

2.51km

80m

Hiking

Hike the easy 1.6-mile Chipman Hill Loop in Middlebury, Vermont, offering views of the town, Adirondacks, and Green Mountains.

Last updated: February 26, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Chipman Hill Natural Area

Waypoints

A

Start point

Parking

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Chipman Hill Top Trail

Highlight (Segment) • Trail

Chipman Hill was once the ski hill for Middlebury College, but today is a popular spot for hikers and mountain bikers. The Chipman Hill Top Trail is a strenuous, but enjoyable, trail that takes you around the summit of the hill at its steepest part. Be aware of mountain bikers, who can travel both up and down the Top Trail, as you hike up this popular route.

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B

2.51 km

End point

Parking

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Way Types & Surfaces

Way Types

1.06 km

737 m

562 m

131 m

Surfaces

1.05 km

828 m

490 m

126 m

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Elevation

Elevation

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Highest point (240 m)

Lowest point (160 m)

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Weather

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Sunday 24 May

13°C

8°C

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This route was planned by komoot.

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Frequently Asked Questions

Where can I park to access the Chipman Hill Loop?

The Chipman Hill Loop is conveniently located close to downtown Middlebury, Vermont. While specific parking lots aren't detailed, its proximity to the town center suggests various public parking options would be available nearby, allowing for easy access to the trail network.

Is the Chipman Hill Loop suitable for beginners?

Yes, the Chipman Hill Loop is generally considered suitable for beginners, with many paths being easily accessible. However, some sections, particularly the ascent to the summit and parts of the Chipman Hill Top Trail, can be quite steep and strenuous. Beginners should be prepared for varying terrain and consider their fitness level for these more challenging parts.

What kind of terrain can I expect on the Chipman Hill Loop?

The trail network at Chipman Hill offers a diverse range of surfaces. You'll encounter packed earth, dirt, gravel, crushed stone, and natural paths. There are also some sections with asphalt remnants from old roads. Be aware that some parts can be technical with roots, especially on steeper ascents.

What scenic views or landmarks can I see along the Chipman Hill Loop?

Hikers on the Chipman Hill Loop are treated to wonderful views of the Middlebury town center. From various points, you can enjoy expansive vistas towards the Adirondack Mountains and the Green Mountains. The trail also passes through a dense, regenerated forest. The Chipman Hill Top Trail offers some of the best views. You might even spot remnants of old ski jump hills from its past as a ski area.

Does the Chipman Hill Loop connect with other trails?

Yes, the Chipman Hill Loop is part of a larger network. It connects with the extensive Trail Around Middlebury (TAM) network, offering options for longer hikes. The route also passes through sections of the MTB TAM, North Country National Scenic Trail (VT), Chipman Hill Top Trail, and other local paths like Rehab and Sidewinder.

Is the Chipman Hill Loop dog-friendly?

Chipman Hill is a beloved destination for walkers and hikers, and it is generally considered dog-friendly. However, specific leash regulations are not detailed, so it's always best to keep your dog under control and follow local signage regarding pets.

Are there any fees or permits required to hike in the Chipman Hill Natural Area?

No, there are no specific fees or permits required to access and hike the trails within the Chipman Hill Natural Area. It is a publicly accessible natural space for recreation.

What is the best time of year to hike the Chipman Hill Loop?

The Chipman Hill Loop can be enjoyed year-round. Spring offers lush greenery, summer provides shade from the dense forest, and fall showcases vibrant foliage. Winter hiking is also possible, but be prepared for snow and ice, as conditions can vary. Each season offers a unique experience.

How long does it typically take to complete the Chipman Hill Loop?

The Chipman Hill Loop, as described, typically takes around 45 minutes to complete. This duration can vary based on your pace, how often you stop for views, and which specific paths you choose within the network.

Are there any specific sections of the trail that are particularly challenging or rewarding?

The ascent to the summit, particularly via the Chipman Hill Top Trail, is known for being the steepest and most challenging part, sometimes featuring roots. However, reaching the top offers rewarding panoramic views of Middlebury and the surrounding mountains. Exploring the old ski jump hills can also be a unique experience.

Are there cafes or amenities near the Chipman Hill Loop trailhead?

Yes, Chipman Hill's close proximity to downtown Middlebury means you'll find various cafes, restaurants, and other amenities just a short walk away from the trail access points. It's easy to grab a coffee or a meal before or after your hike.

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