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Routes
Hikes
United States
Vermont
Windham County

Chimney Hill

The best walks and hikes around Chimney Hill

5.0

(6)

65

hikers

8

hikes

Hikes around Chimney Hill are located in the Green Mountains of Southern Vermont. The terrain is characterized by forested mountain slopes, including mature hardwood, spruce, and fir woodlands, with trails leading to summits and scenic ponds. The area's routes follow old railway beds, cross wooden bridges, and pass through fields, with some connecting to the larger trail network in the Hogback Mountain Conservation Area.

Best hiking trails around Chimney Hill

  • The most popular hiking route is the Haystack Mountain loop from Chimney Hill, a 4.0 mile (6.4 km) trail that takes about 2 hours 2 minutes to complete. This moderate hike ascends Haystack Mountain, offering views over the Deerfield Valley.
  • Another top favourite among local hiking enthusiasts is the Mount Olga loop — Molly Stark State Park, an easy 1.8 mile (2.8 km) path. The trail leads to a historic fire tower at the summit of Mount Olga.
  • Local hiking enthusiasts also love the Hoot Toot & Whistle Trail to Molly Stark statue — Wilmington, Vermont, a 4.2 mile (6.8 km) trail along the shore of the Harriman Reservoir, often completed in about 1 hour 47 minutes.
  • Hiking around Chimney Hill is defined by forested mountain trails, lakeside paths, and routes through the Deerfield Valley. The network of trails provides options suitable for different ability levels, from easy walks to more difficult mountain ascents.
  • The routes in Chimney Hill are highly rated by the komoot community with an average score of 5.0 stars from more than 10 reviews. More than 130 hikers have used komoot to explore Chimney Hill's varied terrain.

Last updated: April 30, 2026

16

hikers

#1.

Haystack Mountain Trail

3.31km

00:59

0m

280m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

1

hikers

4.34km

01:13

100m

50m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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5.0

(5)

24

hikers

2.85km

00:56

130m

140m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

13

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

Hard
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Popular around Chimney Hill

Road Cycling Routes around Chimney Hill

Cycling around Chimney Hill

Running Trails around Chimney Hill

Tips from the Community

Lisa
October 12, 2023, Hoot Toot & Whistle Trail

The Hoot Toot & Whistle Trail follows an old railbed, once owned by a railroad of the same name. You can follow it from the boat launch alongside the Deerfield River all the way into town, or vice versa.

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Lisa
October 12, 2023, Molly Stark statue

This statue honors Elizabeth Page "Molly" Stark, the wife of General John Stark, who won the Battle of Bennington during the American Revolutionary War. Molly herself is said to have been a staunch, fierce, and devoted woman during the difficult times of war.

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Lisa
October 12, 2023, Mount Olga

Mount Olga stands just 2,415 feet (737 m) tall, but still offers grand views over the surrounding landscape — especially if you climb the fire lookout tower at the summit.

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From the top of this mountain you are close to the ski resort "L'Ermitage". You also have exceptional views, especially on the Harriman Reservoir.

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Vincent Reboul
December 22, 2022, Valley Trail

This valley trail takes you straight to the town of Willmington. It starts not far away from the Deerfield Valley Regional Airport.

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Frequently Asked Questions

Are there any dog-friendly hiking trails around Chimney Hill?

Yes, many trails in the Chimney Hill area are welcoming to dogs, provided they are kept on a leash. The region's forested paths and wide-open spaces are great for exploring with your canine companion. Always remember to bring water for your dog and to clean up after them to keep the trails beautiful for everyone.

What are some good hikes for beginners in the Chimney Hill area?

For those new to hiking, the area offers several accessible options. The Hoot Toot & Whistle Trail is an excellent choice. It follows an old, relatively flat railway bed along the shore of the Harriman Reservoir, making for a gentle and scenic walk.

Are there any family-friendly trails suitable for children?

Absolutely. The trails in Molly Stark State Park are great for families. The Mount Olga loop is a short, manageable hike of under 2 miles that leads to a historic fire tower at the summit, which kids often find exciting.

What is the best time of year to hike around Chimney Hill?

Hiking is popular from late spring through fall. Summer offers lush green forests, while autumn provides spectacular fall foliage, a quintessential Vermont experience. Winter is also an option for experienced hikers prepared with snowshoes or microspikes, as many trails are covered in snow.

Can I go snowshoeing on the trails in winter?

Yes, many of the hiking trails around Chimney Hill and in nearby Molly Stark State Park and Hogback Mountain Conservation Area are suitable for snowshoeing in the winter. The trails offer a quiet, serene experience through the snow-covered woodlands. Always check conditions before you go.

Are there any challenging hikes for experienced hikers?

For a more demanding adventure, consider the Hike Haystack Mountain via Valley Trail. This difficult route is nearly 12.4 miles (20 km) long and involves significant elevation gain, rewarding seasoned hikers with a true Green Mountains challenge and expansive views.

Where can I find the best scenic viewpoints on the trails?

For breathtaking views, the summit of Haystack Mountain is a must-see, offering a 180-degree vista of the Deerfield Valley. Another fantastic viewpoint is from the historic fire tower at the top of Mount Olga, which provides 360-degree panoramic views of the surrounding Green Mountains.

What is the terrain like on the trails around Chimney Hill?

The terrain is quite varied. You'll find everything from gentle paths on old railway beds to classic mountain trails with rocky sections and significant elevation changes. Most routes travel through mature hardwood and fir forests, with some crossing streams, passing old stone walls, and opening up into fields.

How do komoot users rate the hiking in Chimney Hill?

The hiking routes around Chimney Hill are very highly regarded by the komoot community, which has given the area an average rating of 5.0 stars. Hikers often praise the well-maintained trails, beautiful forest scenery, and the variety of routes available for all skill levels.

Are there any longer, moderate hikes available?

Yes, if you're looking for a longer day out without extreme difficulty, the Valley Trail to Mirror Lake is a great moderate option. It's a substantial hike of about 10.2 miles (16.5 km) that explores the wider valley and leads to the scenic Mirror Lake.

What should I pack for a day hike in this area?

For a day hike, you should bring plenty of water, snacks, and a map of the area. Weather in the Green Mountains can change quickly, so it's wise to pack layers of clothing, including a waterproof jacket. Sturdy hiking shoes are essential due to the varied terrain. For safety, a first-aid kit and a fully charged phone are also recommended.

Is there parking available at the trailheads?

Yes, parking is available for most major trails. The Haystack Mountain trailhead has parking on Upper Dam Road within the Chimney Hill development. Molly Stark State Park and the Hogback Mountain Conservation Area also have designated parking areas. It's always a good idea to arrive early on weekends, especially during peak season, as lots can fill up.

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