9 Best Southern Vermont Hikes for All Levels

The red wooden Silk Road Covered Bridge in Bennington, Vermont

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Looking for the best Southern Vermont hikes for some outdoor fun and adventure? Whatever level of experience you have, there are plenty of fantastic options in the Green Mountain State.

Southern Vermont generally encompasses anything south of Route 4, which crosses the state going east-west between New York and New Hampshire.

As the gateway to Vermont from points south, visitors are rewarded with lush forests, classically quirky Vermont towns, and interesting history in this region.

From the Green Mountain National Forest to lovely Molly Stark State Park and beyond, these are the best hiking trails in Southern Vermont that all outdoor enthusiasts should seek out.

You might also like our guide to hiking around Stowe VT or head one state over with these best hikes in New Hampshire.

If you’re an avid hiker, don’t miss these top East Coast hiking trails.

Favorite Hikes in Southern Vermont

When hiking in Southern Vermont, take advantage of the many other fun things to do in the area!

You might like our guide to the best places to visit in Vermont for destination inspiration.

And definitely seek out the historic and iconic covered bridges; there are multiple in Bennington, which also hosts one of our recommended hikes in this guide.

Keep in mind the season, too.

Spring in Vermont can be perfect for hiking, but the cusp between winter and spring is known as mud season in VT and you’ll want to avoid most trails.

Silk Road Covered Bridge Bennington in Vermont

Mount Ascutney, Ascutney State Park

Mount Ascutney sits in the 2,362-acre Mount Ascutney State Park, one of Vermont’s first state parks.

It is said to be the first mountain in the US with a developed hiking trail and is certainly a popular place for hiking in southern Vermont. 

In the 1930s, the Civilian Conservation Corps (CCC) was formed to create work for young men in the Depression era; they created the parkway up the mountain, as well as stone toilet buildings and ranger’s quarters. 

The name “Ascutney” comes from several Abenaki words that translate to “mountain of the rocky summit.”

At 3,144 feet high, the peak is particularly prominent; it isn’t part of a mountain range and therefore has a commanding presence in the landscape.

The geological term for mountains that stand alone like this is “monadnock,” which is derived from another Abenaki word.

The Windsor Trail, Weathersfield Trail, and Brownsville Trail are the three main trailheads for Mount Ascutney, making up a total of 12 miles of trails. 

If you’re not up for a long hike, you can drive the 3.7-mile Mount Ascutney Parkway for great views.

At the end of the road, there is a one-mile round-trip trail leading from the parking lot to the summit.

There is also a 25-foot-tall viewing platform at the top, made from the mountain’s fire tower.

West Peak is a very popular launch spot for hang gliders, so keep your eyes peeled!

The Stone House Farm is a beautiful place to stay in nearby Cavendish to base yourself for hiking Mt Ascutney and more.

Editor’s Note: My aunt and her family actually lived on Mt. Ascutney, so I grew up visiting here for holidays and vacations; it’s gorgeous!

Vista Trail, Emerald Lake State Park

At only 28 acres, Emerald Lake makes up for its small size with its striking green waters. 

The lake sits inside Emerald Lake State Park, which offers about 430 acres to enjoy, including several campgrounds.

From Emerald Lake, the longest river in Vermont originates, known as Otter Creek.

The Green Mountains rise up on the eastern side of the lake and the Taconic Mountains rise up on the west, creating a dramatic location.

The 2.4-mile Vista Trail provides lovely views of Emerald Lake and the Taconic Mountains.

For an easy walk, you can take the Lake Trail that hugs the shoreline.

The park is staffed with an interpreter, which makes it an educational place for hands-on learning about the natural and cultural history of the park.

For a quintessential Vermont experience after your hike, be sure to visit the Vermont Country Store where you can also visit the Kissing Bridge.

Check out our Vermont covered bridges guide for more information.

Merck Forest and Farmland Center, Rupert

Merck Forest is home to one of the most extensive selections of hiking trails in Southern Vermont.

The Center has an impressive 3,200 acres of both natural and farmland.

It is a unique place to learn about both natural and working lands.

Traversed by 31 miles of trails, the center has something for everyone.

The Silviculture Trail is 2.3 miles long and provides an opportunity to learn about sustainable forestry practices.

The Lookout Trail is the most challenging route but is a beautifully secluded 6-mile hike through the forest.

There are plenty more trails to be enjoyed, but if you don’t feel like a walk, you can always choose to visit the farm instead.

Lye Brook Falls, Manchester

The 15,680-acre Lye Brook Wilderness is near Manchester, and the Lye Brook Falls Trail is one of the most popular southern Vermont hiking trails.

The trail can be quite busy so an early morning start is a good idea.

The Lye Brook Falls Trail is 4.6 miles round trip.

A moderate hike, the falls can be reached in around 2 hours, making it a great option for a partial day out.

Shaded the whole way, it’s a perfect choice for a hot summer day.

The falls are 125 feet tall and made up of a series of cascades and horsetails.

Once a very active logging area, nature has once again been able to reclaim the wilderness over the last century.

If you want to combine your outdoor adventures with some US history, Hildene, the estate of Abraham Lincoln’s son Robert, is an interesting place to visit nearby.

Their mission is to “carry the values of Abraham Lincoln to future generations by educating and inspiring others to put those values into action.”

Vermont First Congregational Church of Manchester at fall

Blue Line Summit Trail, Mount Equinox, Manchester Area

When looking for challenging hikes in the Green Mountains, Vermont hiking enthusiasts should not miss Mount Equinox.

Located near Manchester, it is the highest peak in the Taconic range at 3,840 feet. 

The 6.2-mile round trip Blue Summit Trail gets you to the top of the mountain, and the trailhead and parking can be found at the end of West Union Street in Manchester.

There is a staggering 2,800 feet of elevation gain in 3 miles, the last mile being the steepest.

Due to this significant elevation gain, this is not a mountain for beginners, and plenty of time should be allowed to complete the hike.

There is a road to the top; however, if you do not wish to take on such a hike, so you can still see the views, which can reach all the way to Montreal on a clear day.

Once you’ve reached the summit, it’s worth the extra 2/10ths of a mile walk to Lookout Rock.

There is a visitors center on the summit, which is a great place for shelter if the weather takes a turn, or just to take a refresher after your hard work.

Aiken Wildflower Trail and Hadwen Woods, Bennington

“What a wonderful thing it would be if just outside every city or large town there could be established a wildflower preserve.” – George Aiken

Senator George Aiken was a widely respected Vermont congressman and a pioneer in the propagation of wildflowers.

The Aiken Wildflower Trail is adjacent to the Bennington Museum and highlights many of the species Aiken featured in his book Pioneering with Wildflowers.

This peaceful walk is only 1/3 mile long and is a perfect choice for those looking for a short walk.

You can also extend your walk into the neighboring Hadwen Woods.

The trail has identification markers and information panels, making it a “learning laboratory” for all visitors.

Be sure to pop into the Bennington Museum next door after completing your hike!

Bennington is a cute town that features in our Vermont bucket list.

Bennington Visitor Center, Vermont fall colors

Hoot Toot and Whistle Trail, Wilmington

This is a great trail for kids, both for the easy terrain and the fun name.

It follows the line of the old Hoosac, Tunnel, and Wilmington Railroad, so it’s an easy grade.

To save space on the sides of the locomotives, the railroad name was shorted to initials, and it simply said “HT&W” which turned into the affectionate “Hoot Toot and Whistle” nickname.

There are several ways to get to the trail, one from the Riverwalk and the other from Mill Street.

In addition to 2 miles of trails, there is a swimming beach and boat launch.

Haystack Mountain, Wilmington

When it comes to options for Green Mountain hiking, Vermont’s Haystack Mountain should be high on your list.

Haystack, aptly named for its shape, is an imposing 3,445 feet tall and shares a ridgeline with Mount Snow above the Deerfield Valley.

In 1861, Edward Hitchcock said of Haystack Mountain that it was “one of the wildest, most rugged, and imposing peaks in Southern Vermont.”

The trailhead is located at the back of Chimney Hill Development and does not have designated parking.

If you have a clear day, you might be able to see as far as Mount Monadnock in New Hampshire.

In addition to mountain views, the picturesque Haystack Pond can be seen from the summit at an elevation of 2,984 feet.

An interesting fact about Haystack Pond is that it doesn’t support any aquatic life due to its high acidity!

After working up an appetite on your hike, you can grab a bite to eat at the rustic Wilmington Roadhouse.

Mount Olga, Molly Stark State Park (Wilmington)

The 2,145-foot Mount Olga is a moderate 1.7-mile round-trip hike situated in Molly Stark State Park.

With an elevation gain of 520 feet, it’s very manageable for most fitness levels and is one of the best hikes in southern Vermont for families.

The park gets its name from Molly Stark, wife of famed Revolutionary General John Stark.

In 1777, General Stark roused his troops at the Battle of Bennington with the words, “There are the Redcoats, and they are ours, or this night Molly Stark sleeps a widow.”

The mountains are a peaceful place now, as the path to the top leads you through forests of hardwoods, spruce, and fir.

At the summit sits a steel fire tower, which was relocated from Balk Mountain and is a registered national landmark.

The tower is open to the public and at the top, you can bask in a beautiful view above the forest canopy.

West Branch Batten Kill Manchester Vermont

Final Words

Have you completed all of these Southern Vermont hiking trails? Let us know your favorites in the comments below!

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