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Vermont
Bennington County

Old Bennington

Easy hikes and walks around Old Bennington

4.8

(5)

68

hikers

14

hikes

Easy hiking trails around Old Bennington are situated within the Green Mountains and Taconic Range, offering a landscape of dense forests and rolling hills. The region features varied terrain, including paths that follow waterways like Paran Creek and trails that ascend to viewpoints. Hikers can experience the natural beauty of Vermont's valleys and distant mountain vistas.

Best easy hiking trails around Old Bennington

  • The most popular easy hiking route is The Mile-Around Woods, a 1.6 miles (2.6 km) trail…

Last updated: October 16, 2026

3

hikers

#1.

The Mile-Around Woods

2.56km

00:41

30m

30m

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

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Easy

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

Easy
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5.0

(2)

13

hikers

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

Easy

5.0

(1)

4

hikers

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

Easy

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

Easy
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Tips from the Community

Jamie S.
April 12, 2023, Carriage Road (Grove Road)

The Carriage Road is how most begin (and often end as well) their hike in the scenic, pastoral Mile-Around-Woods area. This bucolic segment of trail is west of the Park-McCullough Historic Governor's Mansion and follows a treed, old carriage road through some farm fields. This section of the Mile-Around-Woods is particurlaly stunning in the fall when the leaves are changing from green to bright hues of orange, yellow, and red.

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Jamie S.
April 12, 2023, The Ledges

The Ledges is a clear, scenic spot in the from which you can see Mount Anthony, North Bennington, and the surrounding area across open fields. This is a great place to snap some photos of this classic New England vista as you amble around the beautiful Mile-Around-Woods area.

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Right from the parking area the Harmon Hill Trail takes you up steep, root and moss-covered, stone stairs that wind through the thick forest. Fortunately (depending on your outlook, of course), this is the steepest part of the trail and is out of the way first when traveling up to 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 easy hiking trails are there around Old Bennington?

There are 5 easy hiking trails specifically highlighted in this guide for Old Bennington. In total, the area boasts 14 diverse routes, ranging from easy to more challenging, offering plenty of options for all skill levels.

Are there any family-friendly or kid-friendly easy hikes?

Absolutely! Many of the easy trails are perfect for families. For instance, The Mile-Around Woods offers a gentle, quiet woodland experience. The Lake Paran loop from Shaftsbury is another excellent choice, providing flat pathways and scenic views of the lake, which is also a hub for swimming and kayaking.

What kind of natural features can I expect to see on easy hikes in Old Bennington?

Old Bennington's easy trails often wind through dense forests, past rolling hills, and alongside picturesque waterways like Paran Creek. You might encounter curated native plants on trails such as the George Aiken Wildflower Trail, or enjoy views of the Green Mountains and Vermont Valley. Some trails, like those near Lake Paran, offer beautiful lakeside scenery.

Are there any easy circular routes available?

Yes, several easy circular routes are available. The Mile-Around Woods is a popular easy loop that meanders through woodlands and meadows. Another great option is the Lake Paran loop from Shaftsbury, which offers a pleasant circuit around the lake.

Can I bring my dog on these easy trails?

Most trails in the Old Bennington area, including many easy ones, are dog-friendly. However, it's always best to check specific trail regulations before you go. Generally, dogs should be kept on a leash to protect wildlife and ensure a pleasant experience for all hikers.

What are some interesting landmarks or viewpoints along the easy hiking trails?

Many easy trails offer scenic viewpoints and access to historical landmarks. For instance, the Carriage Road, a beginner-friendly path, provides views of the Bennington Battle Monument and the Vermont Valley. The Harmon Hill via the Appalachian Trail, while a bit longer, leads to an open summit with expansive views over the town and surrounding ranges.

What is the best time of year to hike easy trails in Old Bennington?

Old Bennington is beautiful year-round, but many hikers particularly enjoy the spring for wildflowers and the autumn for spectacular fall foliage. The dense forests and rolling hills transform into a vibrant display of colors, making it an ideal time for scenic walks. Summer offers lush greenery, while winter can provide serene, snow-covered landscapes for those prepared for colder conditions.

Are there short easy hikes for a quick outing?

Yes, if you're looking for a quick and easy outing, the Waters Hill Cemetery Trail is a great option, offering a shorter distance with some elevation. Another excellent choice for a brief walk is The Mile-Around Woods, which is just over 2.5 km.

What do other hikers enjoy most about the easy trails in Old Bennington?

The komoot community rates the trails in Old Bennington highly, with an average score of 4.5 stars. Hikers often praise the quiet woodlands, well-maintained paths, and the beautiful natural scenery. The accessibility and variety of easy routes, from lakeside loops to paths with historical views, are frequently highlighted as major draws.

Is parking readily available for these easy hiking trails?

Parking is generally available at trailheads and popular access points for many of the easy trails in and around Old Bennington. For specific routes, it's advisable to check the tour details on komoot, as parking information is often included there.

What makes a trail 'easy' in the Old Bennington area?

Trails designated as 'easy' in Old Bennington typically feature gentle slopes, minimal elevation gain, and well-maintained, clear paths. They are suitable for most fitness levels, including beginners, families with children, and those looking for a leisurely stroll rather than a strenuous workout. These routes often have shorter distances and can be completed in a relatively short amount of time.

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