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United States
Vermont
Windham County

Chimney Hill

Easy hikes and walks around Chimney Hill

5.0

(6)

68

hikers

9

hikes

Easy hiking trails around Chimney Hill are situated in Southern Vermont, within a region characterized by forested mountain slopes and mature hardwood, spruce, and fir woodlands. The area is part of the Green Mountains, with features like Haystack Mountain and Mount Olga offering varied terrain. Hikers can find paths leading through the Deerfield Valley and alongside the Harriman Reservoir.

Best easy hiking trails around Chimney Hill

  • The most popular easy hiking route is Haystack Mountain Trail, a 2.1 miles…

Last updated: July 13, 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)

26

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

5.0

(1)

11

hikers

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

Easy
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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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Frequently Asked Questions

How many easy hiking trails are available around Chimney Hill?

There are several easy hiking trails around Chimney Hill. This guide features 5 routes specifically categorized as easy, perfect for a relaxed outdoor experience.

What kind of scenery can I expect on easy hikes around Chimney Hill?

The easy hikes around Chimney Hill primarily take you through the beautiful forested mountain slopes of the Green Mountains, featuring mature hardwood, spruce, and fir woodlands. You'll find picturesque landscapes, including views over the Deerfield Valley and paths along reservoirs like the Harriman Reservoir.

Are there any easy circular walks in Chimney Hill?

Yes, for an easy circular walk, consider the Mount Olga loop from Molly Stark State Park. This route offers a pleasant, manageable loop perfect for a relaxed outing.

Are the easy hiking trails around Chimney Hill suitable for families with children?

Absolutely. Many of the easy trails are ideal for families. For example, the Mount Olga Trail is a relatively short path that leads to a historic fire tower, which can be an exciting destination for kids. The Hoot Toot & Whistle Trail also offers a gentle, scenic walk along the Harriman Reservoir.

Can I bring my dog on the easy hiking trails?

Generally, dogs are welcome on many trails in the Chimney Hill area, especially in national forests and state parks, but it's always best to check specific park regulations or trail signage beforehand. Always keep your dog on a leash and practice leave-no-trace principles.

What are some notable natural features or viewpoints I can find on easy hikes?

On easy hikes, you can enjoy several natural features. The Mount Olga summit, accessible via an easy path, offers panoramic views from its historic fire tower. You might also encounter scenic spots like the West Side of Adams Reservoir, which is particularly beautiful in the fall.

Are there any trails that follow old railway beds?

Yes, some routes in the Chimney Hill area follow old railway beds, offering relatively flat and easy walking surfaces. The Old Rail bed is a notable highlight that provides a glimpse into the region's history while offering a pleasant walk.

What is the best time of year to enjoy easy hikes around Chimney Hill?

The Chimney Hill area is beautiful year-round. Spring brings lush greenery, summer offers pleasant temperatures for shaded walks, and autumn is spectacular with vibrant fall foliage, especially around Adams Reservoir. Even winter can be enjoyable for snowshoeing or cross-country skiing on some trails, though conditions vary.

Where can I find parking for easy hikes in the area?

Parking availability varies by trailhead. For trails like the Mount Olga loop from Molly Stark State Park, designated parking areas are typically available within the state park. For other trails, look for small parking lots or roadside pull-offs near the trailheads. Always check local signage for parking regulations.

What do other hikers enjoy most about hiking in Chimney Hill?

The komoot community highly rates the hiking experience around Chimney Hill, with an average score of 5.0 stars. Reviewers often praise the quiet woodlands, the well-maintained paths, and the rewarding views from summits like Mount Olga, making it a favorite for peaceful and accessible outdoor adventures.

Are there any easy trails that offer lakeside views?

Yes, the Hoot Toot & Whistle Trail is an excellent option for lakeside views, as it follows the shore of the Harriman Reservoir. Another great choice is the Lake Raponda Trail, which offers scenic perspectives of Lake Raponda.

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