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Windham County

Routes
Hikes

Windham County

The best family-friendly hikes and walks in Windham County

4.8

(56)

857

hikers

11

hikes

Family friendly hiking trails in Windham County, Vermont, offer diverse landscapes for outdoor enthusiasts. The region is characterized by its forested mountain slopes, tranquil lakes, and a variety of parks. An extensive network of trails winds through lush forests, providing options for various skill levels. These paths often feature minimal elevation changes, making them suitable for families.

Best family friendly hiking trails in Windham County

  • The most popular family friendly hiking route is Lowell Lake loop, a 3.2 miles…

Last updated: May 27, 2026

4.6

(8)

46

hikers

#1.

Lowell Lake loop

5.16km

01:20

30m

30m

Hike the easy 3.2-mile Lowell Lake loop in Vermont, offering scenic views of Lowell Lake and its forested surroundings.

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Easy

5.0

(1)

19

hikers

4.34km

01:11

60m

60m

Hike the easy 2.7-mile Grout Pond Loop Trail in Vermont's Green Mountain National Forest for picturesque pond views and vibrant fall foliage

Easy
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13

hikers

Hike the easy 4.2-mile Hoot Toot & Whistle Trail near Wilmington, Vermont, featuring river views and historical railroad beds.

Easy

7

hikers

11.8km

03:15

190m

190m

Hike the moderate 7.4-mile Stratton Pond Trail in Green Mountain National Forest, gaining 624 feet to a scenic glacial pond.

Moderate

2

hikers

12.1km

03:15

140m

140m

Hike the moderate 7.5-mile West River Trail in Brattleboro, Vermont, gaining 470 feet with continuous river views and historic railroad remn

Moderate
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Popular around Windham County

Family-friendly hikes in Fort Dummer State Park

Roundabout Brattleboro — a charming challenge in the New England countryside

Other adventures in Windham County

Roundabout Brattleboro — a charming challenge in the New England countryside

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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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Zachary
September 22, 2023, West River

The West River flows south along the path to Brattleboro, where it merges with the Connecticut River at the Vermont - New Hampshire border. The trail here is a nice scenic bike path with views of the river and Black Mountain to the north.

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Here you can hike up the trail to Black Mountain, which is a beautiful forested trail with a number of water features. Hiking along the West River Trail for the mile south of here you get nice views of the mountain.

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You park near the marina at the southern end of Spring Tree Road in a large gravel lot by the river. From here you follow the river north on the road to where it quickly becomes a bike path.

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Lisa
September 22, 2023, Grout Pond Loop Trail

This family-friendly hike takes you all the way around the tranquil waters of Grout Pond, with a few jaunts through the forest too. There's just one problem: Mud. Bog bridges are in place to help you get through the worst of it, but waterproof footwear can be a big help on this sort of terrain.

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Lisa
September 21, 2023, Stratton Pond

Although Stratton Pond isn't directly on the Appalachian/Long Trail, it's close enough that this is a popular camping spot for thru hikers. It's also a great day hiking destination, and you may want to pack a bathing suit to go for a dip in the pond.

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Vincent Reboul
December 22, 2022, Lowell Lake

A lot of activities are possible in this little state park near Londonderry. It includes hiking, non-motorized boating, fishing, picnicking, wildlife watching, as well as winter sports.

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Frequently Asked Questions

How many family-friendly hiking trails are available in Windham County?

Windham County offers a variety of family-friendly hiking options. Our guide features 11 curated routes, ranging from easy strolls to more moderate adventures, ensuring there's something for every family.

Are there any easy loop trails suitable for families with young children?

Yes, Windham County has several easy loop trails perfect for families. The Lowell Lake loop is a popular choice, offering a gentle 3.2-mile path around the lake with minimal elevation change. Another great option is the Grout Pond Loop Trail, which is just over 4 km and also features a relatively flat terrain.

What kind of natural attractions can we see along the family-friendly trails?

Windham County's trails offer diverse natural beauty. You can enjoy serene lake views at Lowell Lake, or discover the impressive Hamilton Falls. Many trails also lead through lush forests, offering opportunities for wildlife spotting and enjoying the peaceful Vermont landscape.

Are there any trails with scenic viewpoints or fire towers?

Absolutely! For panoramic views, consider trails that lead to Mount Olga in Molly Stark State Park, which has a fire lookout tower. Stratton Mountain also offers 360-degree views from its summit fire tower, accessible via longer routes.

What is the best time of year to go hiking with family in Windham County?

Each season offers a unique experience. Spring brings blooming wildflowers, summer provides lush greenery and pleasant temperatures, and fall showcases spectacular foliage. For families, late spring through early fall generally offers the most comfortable weather conditions for hiking.

Are dogs allowed on the family-friendly hiking trails in Windham County?

Many trails in Windham County are dog-friendly, including the popular Pinnacle at Windmill Hill Loop. However, regulations can vary by park or specific trail, especially within state parks and the Green Mountain National Forest. It's always best to check specific park rules beforehand, and always keep your dog on a leash and clean up after them.

Are there any trails that follow a river or have water access?

Yes, the West River Trail in Jamaica State Park is an excellent option. It features packed gravel paths that run along the West River, offering scenic views and easy access to the water in some sections. Lowell Lake also provides beautiful lakeside walking.

What do other hikers enjoy most about the family-friendly trails in Windham County?

The hiking community highly rates the trails in Windham County, with an average score of 4.86 stars. Reviewers often praise the well-maintained paths, the stunning natural beauty, and the variety of options suitable for all ages and skill levels, making it a perfect destination for family outings.

Are there any trails that are particularly good for spotting wildlife?

Areas like Lowell Lake State Park and Grout Pond are known for their tranquil environments, making them ideal for wildlife observation. Keep an eye out for birds, deer, and other small animals, especially during quieter times of the day.

Are there any fees or permits required for hiking in Windham County's parks?

Some state parks, like Molly Stark State Park, Jamaica State Park, and Lowell Lake State Park, may have day-use fees for parking or entry, especially during peak season. Hiking in the Green Mountain National Forest generally does not require permits for day hikes, but it's always good to check for any specific area regulations or parking fees.

Can we find any historical points of interest on these trails?

While the focus is on natural beauty, Windham County has historical significance. For example, Stratton Mountain is where the idea for Vermont's Long Trail was conceived. Many trails pass through areas with a rich logging or agricultural history, offering glimpses into the region's past.

Are there any trails that are relatively flat and suitable for strollers?

For very easy, flat walks, sections of the West River Trail with its packed gravel surface can be suitable for sturdy strollers. The Hoot Toot & Whistle Trail is another easy option with minimal elevation gain, though surface conditions can vary.

Most popular routes in Windham County

Hiking in Windham County

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Fort Dummer State Park

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