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Routes
Hikes
United States
Vermont
Bennington County

South Shaftsbury

The best walks and hikes around South Shaftsbury

4.6

(9)

72

hikers

19

hikes

Hiking around South Shaftsbury, Vermont, offers diverse trails set amidst rolling hills and the Green Mountains. The region is characterized by picturesque landscapes, including the Walloomsac River and Lake Shaftsbury. The geology of the Taconic Mountains, with its limestone and dolostone, contributes to nutrient-rich soils supporting robust northern hardwoods. This natural environment provides varied terrain for outdoor activities.

Best hiking trails around South Shaftsbury

  • The most popular hiking route is Harmon Hill and Scrub Hill, a moderate 8.5 miles…

Last updated: July 12, 2026

8

hikers

#1.

Harmon Hill and Scrub Hill

13.6km

04:17

620m

260m

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Moderate

3

hikers

2.56km

00:41

30m

30m

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

Easy
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5.0

(1)

2

hikers

2.56km

00:39

10m

10m

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

Easy

4.0

(1)

1

hikers

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

Easy

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Popular around South Shaftsbury

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Tips from the Community

Jamie S.
April 7, 2023, Wooden Footbridge

Right next to VT-9 on the Long/ Appalachian Trail is a small stream with wooden foot bridge. This is a nice place to fill water bottles and snap a few photos before continuing onward on the Long/ Appalachian Trail toward the Melville-Nauheim Shelter and Glastenbury Mountain or crossing the road toward the scenic Harmon Hill.

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Jamie S.
April 7, 2023, Harmon Hill

The top of Harmon Hill is covered by huge green ferns and dotted with trees, which stands in stark contrast to the rest of the area which is densely forested. This is because the summit of Harmon Hill is kept clear by controlled burns that allow for fantastic views of the town of Bennington and the surrounding area. This lush meadow is a perfect place to rest, admire the views, and sip some water before continuing on your hike.

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Frequently Asked Questions

How many hiking trails are available in South Shaftsbury?

South Shaftsbury offers a diverse network of over 15 hiking trails. These routes cater to various skill levels, from easy strolls to more challenging ascents, allowing you to explore the region's rolling hills, dense woodlands, and scenic river valleys.

Are there easy hiking trails suitable for beginners or families in South Shaftsbury?

Yes, South Shaftsbury has several easy trails perfect for beginners and families. For instance, The Mile-Around Woods is an easy 1.6-mile path following a carriage road through a pastoral setting, especially beautiful in autumn. Another great option is the Healing Springs Trail in Lake Shaftsbury State Park, which is also 1.6 miles and traverses streams, forests, and wetlands with a boardwalk section for wildlife viewing.

What is the best time of year to go hiking in South Shaftsbury?

While hiking is enjoyable year-round, the autumn months are particularly spectacular in South Shaftsbury due to the vibrant fall foliage. The region's northern hardwoods, including sugar maples, white ash, and red oak, display brilliant hues of orange, yellow, and red. Spring and summer offer lush greenery and pleasant temperatures, while winter provides opportunities for snowshoeing or cross-country skiing on some trails.

Are there any dog-friendly hiking trails in the South Shaftsbury area?

Many trails in and around South Shaftsbury are dog-friendly, but it's always recommended to keep your dog on a leash and follow local regulations. Trails like The Mile-Around Woods and those within the Green Mountain National Forest are generally welcoming to leashed pets.

What kind of natural features or landmarks can I expect to see on hikes in South Shaftsbury?

Hiking in South Shaftsbury offers a variety of natural beauty and interesting landmarks. You can explore the serene 26-acre Lake Shaftsbury within Lake Shaftsbury State Park, or enjoy views of Mount Greylock and the Green Mountains from the Robert Frost Trail. The summit of Harmon Hill provides fantastic panoramic views of Bennington. You might also encounter unique geological features from the Taconic Mountains, which contribute to the area's rich biodiversity.

Are there any circular or loop trails in South Shaftsbury?

Yes, South Shaftsbury offers several loop trails for hikers. An example is the Battle Loop and Valley View Trail, an easy 3-mile route that provides a pleasant circular hiking experience. These loops are great for enjoying varied scenery without retracing your steps.

What do other hikers enjoy most about the trails in South Shaftsbury?

The hiking trails in South Shaftsbury are highly rated by the komoot community, with an average score of 4.6 stars. Hikers often praise the diverse terrain, from peaceful woodlands to scenic overlooks, and the well-maintained paths. The vibrant fall foliage and the opportunity to spot local wildlife are also frequently highlighted as favorite aspects.

Are there any trails that offer historical significance in the area?

Yes, the Robert Frost Trail, connecting Lake Paran to Route 7A, passes through the former farm of renowned poet Robert Frost. This trail offers a glimpse into the landscape that inspired some of his most famous works, including 'Stopping by Woods on a Snowy Evening.' You can also find historical markers and sites related to the region's past, such as the Bennington Battle Monument nearby.

Are there opportunities for winter hiking or snowshoeing in South Shaftsbury?

When conditions permit, many trails in South Shaftsbury and the surrounding Green Mountain National Forest are suitable for winter hiking and snowshoeing. The quiet, snow-covered landscapes offer a unique and serene experience. Always check local conditions and trail accessibility before heading out in winter.

What are the typical lengths and durations of hikes in South Shaftsbury?

Hikes in South Shaftsbury vary significantly in length and duration. Easy trails like Healing Springs Trail are around 1.6 miles and can be completed in under an hour. Moderate routes, such as Harmon Hill via Long Trail, can be about 2.2 miles and take over an hour. Longer, more challenging hikes, like Harmon Hill and Scrub Hill, can extend to 8.5 miles and take over four hours to complete.

Are there any specific trails that offer good wildlife viewing opportunities?

The diverse ecosystems in South Shaftsbury, including forests, wetlands, and river areas, provide excellent opportunities for wildlife viewing. The Healing Springs Trail in Lake Shaftsbury State Park, with its boardwalk section, is particularly good for observing waterfowl and other wetland creatures. Keep an eye out for deer, various bird species, and smaller mammals throughout the region's trails.

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