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Windsor County

Woodstock Village

Routes
Hikes
Windsor County

Woodstock Village

The best family-friendly hikes and walks around Woodstock Village

4.7

(29)

399

hikers

12

hikes

Family friendly hiking trails around Woodstock Village are set within the rolling Green Mountains of Vermont, offering diverse landscapes for outdoor activities. The region is characterized by forested hills, prominent peaks like Mount Tom and Mount Peg, and the serene Ottauquechee River. Hikers can explore well-maintained trail systems that wind through managed forest stands and around picturesque ponds such as The Pogue. This varied terrain provides a range of experiences from gentle riverside strolls to moderate mountain ascents.

Best family…

Last updated: May 13, 2026

2

hikers

#1.

Mount Peg Foot and Bridle Trails

4.14km

01:11

100m

100m

Explore the Mount Peg Foot and Bridle Trails, an easy hiking route that winds through shaded hardwoods and mixed forests. You will encounter rolling hills, with some initial steep sections…

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Easy

4.8

(9)

63

hikers

Hike the moderate 4.4-mile Mount Tom and The Pogue loop for scenic views, diverse forests, and a tranquil pond in Woodstock, VT.

Moderate
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4.6

(8)

50

hikers

Hike the moderate 4.4-mile Mount Tom and The Pogue loop in Vermont, featuring a scenic pond and village views from Mount Tom.

Moderate

5.0

(1)

26

hikers

The Mount Tom loop via the Faulkner Trail offers an easy hiking experience through varied terrain. You will ascend gradually on well-maintained switchbacks, enjoying the atmosphere of Marsh-Billings-Rockefeller National Historical…

Easy

5.0

(3)

23

hikers

Embark on an easy hike along The Pogue loop via The Carriage Road, a pleasant 3.9-mile (6.3 km) route that takes about 1 hour and 48 minutes to complete. You'll…

Easy
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Tips from the Community

Ted
September 29, 2024, The Pogue

Beautiful reflections in the falls.

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A very idyllic small town post office. Very cute.

Translated by Google

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There really is EVERYTHING to walk here. Very pretty little town in Vermont, a postcard idyll.

Translated by Google

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Very pretty small town in Vermont, postcard idyll.

Translated by Google

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Natalie
December 13, 2023, Westerly Bridge

Woodstock Middle Covered Bridge has spanned the Ottauquechee River since 1969 and was supposedly constructed without the use of any nails.

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Jamie S.
May 18, 2023, Mount Peg

Mount Peg is a short summit just a few minutes from the main street of Woodstock, Vermont. Standing at just 1,080 feet, Mount Peg is a popular spot with hikers and mountain bikers in the summer and snowshoers and skiers in the winter. The trails on the east side of the mountain are actually groomed in the winter for nordic skiing. At the summit there is a picnic table and some benches, and great views over the town of Woodstock, Mount Tom, and the Ottauquechee River Valley.

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This spot is a wonderful viewpoint on the Faulkner trail on the southeast side of Mount Tom. From this clearing in the forest you get fantastic views over the town of Woodstock and the surrounding area. While this is a lovely spot all year round, it is exceptionally beautiful in the falls when the leaves are changing; this is a great place to enjoy some classic New England peak foliage!

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The Carriage Barn Visitor Center is open from 10am-5pm, Memorial Day weekend until October 31. The building was constructed on the foundation of a stable that the Billings Family originally erected in 1895 to house their horses and carriages. The main floor of this Visitor Center houses an exhibit Conservation Stewardship, a bookstore and a reading area, and restrooms. Park Rangers are there daily to answer any questions you might have. The Carriage Barn Visitor Center is a great place to stop by before exploring the Marsh-Billings-Rockefeller National Historical Park.

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Frequently Asked Questions

How many family-friendly hiking trails are there around Woodstock Village?

There are over a dozen family-friendly hiking trails around Woodstock Village. Our guide features 13 routes, with 9 of them rated as easy and 4 as moderate, ensuring options for various ages and skill levels.

Are there easy hikes suitable for beginners or young children?

Yes, Woodstock Village offers several easy trails perfect for beginners and young children. The Mount Peg Foot and Bridle Trails offer gentle paths through meadows and woods. Additionally, the Ottauquechee River Trail provides a flat, scenic walk alongside the river, ideal for a relaxed family outing.

What are some good loop trails for families in the area?

For families looking for loop trails, the Mount Tom loop via the Faulkner Trail is a popular choice, offering varied landscapes and views. Another excellent option is The Pogue loop via The Carriage Road, which circles a picturesque pond within Marsh-Billings-Rockefeller National Historical Park.

Are there any stroller-friendly walks in Woodstock Village?

While many trails have varied terrain, the historic carriage roads within Marsh-Billings-Rockefeller National Historical Park are generally wide and well-maintained, making them suitable for sturdy strollers. The Ottauquechee River Trail is another flat option that can accommodate strollers, offering pleasant riverside views.

What can we see along the family-friendly hiking trails?

Many trails offer beautiful natural and historical sights. You can explore The Pogue, a scenic pond, or enjoy panoramic views from Mount Tom. The Eshqua Bog Natural Area features a boardwalk path through unique plant life, including lady's slippers. You might also spot historic covered bridges like the Taftsville Covered Bridge nearby.

Are dogs allowed on the hiking trails in Woodstock Village?

Many trails in the Woodstock Village area are dog-friendly, especially those within Marsh-Billings-Rockefeller National Historical Park and on Mount Peg. It's always best to keep your dog on a leash and practice Leave No Trace principles to ensure a pleasant experience for everyone.

What is the best time of year for family hikes in Woodstock Village?

Woodstock Village offers wonderful hiking experiences year-round. Spring brings blooming wildflowers, while summer provides lush greenery. Fall is particularly stunning with vibrant foliage, making it a popular time for scenic walks. Even winter offers opportunities for snowshoeing or gentle walks on packed trails, though conditions vary.

Where can we find parking and trailheads for these family hikes?

Many trails, particularly those within Marsh-Billings-Rockefeller National Historical Park, have designated parking areas and clear trailheads. For example, the Faulkner Trail to Mount Tom is easily accessible from the village green. Mount Peg also has multiple entry points with nearby parking. Specific parking details are often available on individual route pages.

Are there any trails with scenic viewpoints suitable for families?

Absolutely! Both Mount Tom and Mount Peg offer accessible trails that lead to stunning panoramic views. From Mount Tom, you can see Woodstock Village and the surrounding Green Mountains, while Mount Peg provides vistas of the Ottauquechee River Valley. These are rewarding destinations for families seeking memorable views.

What do other hikers enjoy most about hiking in Woodstock Village?

The area is highly rated by the komoot community, with an average score of 4.7 stars. Reviewers often praise the well-maintained trails, the beautiful mix of natural landscapes and historical features, and the accessibility of routes directly from the village. The peaceful atmosphere and scenic beauty are frequently highlighted.

How long do family hikes around Woodstock Village typically take?

Hike durations vary depending on the trail and your family's pace. Easy trails like the Ottauquechee River Trail might take an hour or less. Moderate loops, such as the Mount Tom and The Pogue loop, typically range from 2 to 3 hours, covering distances of 4-5 miles. Our guide provides estimated durations for each route to help you plan.

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