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Windham County

Windham County

Easy hikes and walks in Windham County

4.8

(43)

574

hikers

hikes

Exploring Windham County on foot is a delightful way to connect with nature. To help you make the most of your adventures, we’ve compiled the top easy hikes and walks in Windham County. Perfect for short hikes, kid-friendly excursions, and family-friendly outings, these routes offer something for everyone.

Last updated: October 22, 2025

4.6

(8)

hikers

1. Lowell Lake loop — Lowell Lake State Park

5.16km

01:20

30m

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

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5.0

(2)

hikers

2. Mount Olga loop — Molly Stark State Park

2.85km

00:56

130m

140m

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

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5.0

(1)

hikers

3. Grout Pond Loop — Green Mountain National Forest

4.34km

01:11

60m

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

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5.0

(1)

hikers

4. Black Mountain loop — Black Mountain Natural Area

5.22km

01:46

260m

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

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5. Hoot Toot & Whistle Trail to Molly Stark statue — Wilmington, Vermont

6.77km

01:47

60m

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

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5.0

(1)

hikers

6. Windmill Mountain loop from Brookline

6.17km

01:47

160m

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

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7. Adam Pond loop from Jamaica

3.84km

01:08

100m

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

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8. Mount Olga loop from Wilmington

2.36km

00:41

60m

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

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Easy

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9. West River loop from Chesterfield

5.95km

01:32

30m

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

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10. The Putney Mountain loop from Newfane

2.12km

00:35

30m

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

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Didn’t find what you were looking for?

Check out more Hikes throughout Windham County below and find the perfect route in your destination.

Fort Dummer State Park West Brattleboro West Dummerston Algiers Brattleboro

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Lamoille County Green Mountain And Finger Lakes National Forests Chittenden County Windsor County Orange County Addison County Washington County Bennington County Lake Champlain Rutland County Franklin County Grand Isle County Orleans County Caledonia County Essex County

Easy hikes and walks in Windham County

1. Lowell Lake loop — Lowell Lake State Park

2. Mount Olga loop — Molly Stark State Park

3. Grout Pond Loop — Green Mountain National Forest

4. Black Mountain loop — Black Mountain Natural Area

5. Hoot Toot & Whistle Trail to Molly Stark statue — Wilmington, Vermont

6. Windmill Mountain loop from Brookline

7. Adam Pond loop from Jamaica

8. Mount Olga loop from Wilmington

9. West River loop from Chesterfield

10. The Putney Mountain loop from Newfane

Other adventures in Windham County

Most popular routes in Windham County

Most popular attractions in Windham County

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