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.
Last updated: April 30, 2026
16
hikers
3.31km
00:59
0m
280m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
1
hikers
4.34km
01:13
100m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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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.
13
hikers
6.77km
01:47
60m
60m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
19.9km
06:02
670m
670m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
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Popular around Chimney Hill
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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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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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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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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