Incredible (and Easy) Southern Vermont Hiking Trails for Fall Foliage

Vermont is beautiful in all four seasons, and exploring the mountains and valleys on foot is one of the most enchanting things to do in the state.

Scenes from some of our favorite Southern Vermont hikes.

We’ve been meandering Southern Vermont’s trails for the past 16 years, and we figured it was high time we shared our favorite trails with you.

The following hikes, rambles, and walks are perfect for novice hikers or families with children. Most are under five miles, and all have a kid-friendly feature to help entice them along.

Today, we’re going to focus on easy hiking trails in Southern Vermont that are perfect for fall foliage, including trails in Bennington, Manchester, Dorset, Stratton, Wilmington, Brattleboro, and Putney.

Cover of book: AMC's Best Day Hikes in Vermont.

Featured Read: AMC’s Best Day Hikes in Vermont

Written by Tara Schatz and Jen Lamphere Roberts, this fully revised guide includes classic hikes such as Camel’s Hump, Mount Mansfield, and sections of the Long and Appalachian trails, along with new additions Raven Ridge, Killington Peak, Moose Bog, and more.

Whether you’re looking for an exploration of nature or to bag a 4,000-footer, AMC’s Best Day Hikes in Vermont is indispensable.

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Insider tip: cell service is spotty in many of these spots. I use AllTrails Plus to download maps before leaving home so I can use the GPS feature without cell service. Use my affiliate link to save 30% on the annual subscription ($25.19 instead of $35.99).

Easy Hiking Trails in Southwestern Vermont

Southwestern Vermont is our home turf, so we have many suggestions for fun, easy hikes in the area.

Lake Shaftsbury State Park: Shaftsbury, Vermont

An autumn view from the beach at Lake Shaftsbury State Park. These are our best hikes for kids in Southern Vermont

This 84-acre park is small but well-loved. It is most popular with local families as a picnic and swimming spot, but the trail around Lake Shaftsbury is underappreciated and quite lovely.

The hike around Lake Shaftsbury is more of a ramble — a mile in length, meandering through the woods, then wetlands, then back into the woods, with a constant view of the lake.

Waterfowl are plentiful most of the year, and we’ve also spotted bald eagles and osprey on numerous occasions.

After your hike, you will want to spend some time on the water, and the beach is the perfect spot for relaxing with a good book.

Afterward, I highly recommend driving south on Route 7A for another mile and visiting the Chocolate Barn for the best ice cream you’re ever likely to taste in Southern Vermont.

Woodford State Park: Woodford, Vermont

Fall foliage in Woodford State Park, Vermont. — Fall at Woodford State Park

The hiking trail in Woodford State Park brings you around Adams Reservoir, a gorgeous, tree-lined lake nestled in the Green Mountains. Woodford State Park is much more secluded than Lake Shaftsbury and much cooler (temperature-wise).

We’ve seen moose up here and spent days on the water without running into another person.

The trail around the lake isn’t difficult, but at 2.7 miles, it might be hard for younger kids to make it around. You can shorten the trail to about 1.8 miles by starting at the day parking lot, hiking counter-clockwise, and cutting into the campground to walk back to your car on the park road.

We love how dark and mossy the trail is. There are several easy stream crossings, and if you look very carefully along the lake shore, you may even see the carnivorous sundew plants.

Equinox Pond Loop: Manchester, Vermont

Equinox Pond during fall foliage in Manchester, Vermont. — Early fall foliage at Equinox Pond in Manchester, Vermont

Some of the best hiking around Manchester can be found a short drive from the town center. The Equinox Preservation Trust is a 914-acre preserve that covers a large chunk of Mount Equinox.

The preserve’s trails range from leisurely to intense, but one of our favorite relaxing walks is taking the Flatlander Trail to Equinox Pond.

While the pond itself is privately owned, the views from the trail are spectacular, especially in the fall.

Mile Around Woods, North Bennington, Vermont

The fields are located next to the Mile Around Woods trail in North Bennington.

If you’re looking for an easy walk with pastoral views, the Mile-Around-Woods trail is one of the best hikes in Southern Vermont. It sits behind the beautiful Park McCullough house in North Bennington, VT, which is worth a visit in its own right.

This loop starts by taking hikers through beautiful farm fields of grazing horses, then meanders through a hardwood forest on a lovely, wide path.

The forest loop is exactly a mile long, but you can extend the adventure by traipsing across several fields or visiting the historic Park McCullough House and Hiland Hall gardens.

I recommend making an afternoon of it; the Park McCullough House is open for tours on Friday, Saturday, and Sunday from May to October.

The Hiland Hall gardens, which have been meticulously restored, are located behind the main house.

For a trail map, please visit the Fund for North Bennington.

Gettysburg Quarry: Dorset, Vermont

The view from Art's Bench near the Gettysburg Quarry in Dorset. — The view from Art’s Bench near the Gettysburg Quarry in Dorset.

Looking for a fun hike that isn’t too difficult and includes rare natural communities along with incredible geological and human history? The Gettysburg Quarry hike in Dorset is a 2.5-mile loop that is perfect for families, history buffs, and nature lovers! It’s also one of our favorite southern Vermont hikes.

The hike to Gettysburg Quarry is a moderate route through a beautiful hardwood forest that leads to an abandoned marble quarry. Marble has been quarried in Dorset since 1785, and the Gettysburg Quarry was in operation from 1866 until 1897.

This 2.5-mile loop is easy enough for kids and dogs and includes a nice viewpoint to the southwest at Art’s Bench.

Before you head out, read our complete trail overview for Gettysburg Quarry.

Hapgood Pond: Peru, Vermont

Hapgood Pond in Vermont — One of the prettiest and easiest hikes in Southern Vermont.

This tiny little pond makes an excellent spot for a picnic, leg stretch, or photo shoot in the fall. While Hapgood Pond is just 12 acres in size and 12 feet deep at its deepest spot, it’s a quiet retreat to enjoy the woods, the views, and a little solitude.

The hike around the pond is about a mile in length, and there’s even a small campground. Campsites are $20 a night and can be booked on Recreation.gov through mid-October. Between October and May, all sites are first-come, first-served.

Easy Hikes in South Central Vermont

The Green Mountains run north to south through the center of the state. The following hikes are located in the southern Green Mountains, which are gorgeous in all four seasons!

Grout Pond: Stratton, Vermont

A fall foliage view of a canoe paddling the calm waters of Grout Pond in Vermont. — Grout Pond in the fall is spectacular!

The Green Mountain National Forest is one of Vermont’s greatest treasures. It encompasses nearly 400,000 acres of rugged mountains, wild woodlands, and secret valleys in southwestern and central Vermont.

Located in Stratton, Vermont, Grout Pond is a popular summer destination, thanks to its clear water for swimming and shoreside campsites.

The 2.7-mile trail around Grout Pond travels past the campground through a lovely wetland and over a small ridge through a hardwood forest.

It’s an easy walk and the perfect way to get some exercise before a relaxing swim.

Grout Pond is an easy drive from Manchester, Vermont, as long as you don’t mind meandering on Kelly Stand Road, one of Southern Vermont’s most beautiful dirt roads, especially in the fall.

Lowell Lake, Londonderry, Vermont

Lowell Lake in Londonderry, Vermont. — Lowell Lake in the fall.

If you’re looking for a peaceful fall foliage hike in southern Vermont, the Lowell Lake Loop in Londonderry is a gem worth adding to your list.

This 3.2-mile loop (with just 154 feet of elevation gain) circles the shoreline of Lowell Lake, offering a mix of lake views, wetland habitats, and quiet stretches of forest.

Plan to spend about 1–1.5 hours meandering along the path; it’s family-friendly, though there are a few uneven sections, narrow boardwalks, and stepping stones to keep things interesting.

Along the way, you’ll pass some fascinating landmarks, including a Revolutionary War–era cemetery tucked into the woods, towering stands of white pine, and occasional openings with beautiful views of the lake framed by fiery autumn leaves. Wildlife is abundant here, too; keep your eyes peeled for herons in the wetlands and songbirds along the trail.

Lowell Lake State Park is a relatively undeveloped park, with no facilities and a focus on keeping the landscape natural.

The lack of crowds makes it even more magical during foliage season when the reflections of red and gold leaves ripple across the water. A small boat launch and parking area provide access to both the trail and the lake, which is also popular with paddlers.

Stratton Mountain Fire Tower, Stratton, Vermont

The gondola at Stratton Mountain Resort during fall foliage. — Photo credit: Stratton Mountain Resort

At 3,940 feet, Stratton Mountain is Southern Vermont’s tallest peak.

The hike to the Stratton Fire Tower from the base of the mountain gains 1,700 feet in elevation and is six miles, round-trip. This is a great hike to aspire to, but it’s not exactly easy!

Fortunately, there’s a shortcut. During summer weekends and every day during the fall foliage season, you can hop aboard the gondola at Stratton Mountain Resort.

From there, it’s an easy 0.7 miles to the fire tower, which provides unparalleled views in all directions.

Mt. Olga, Molly Stark State Park: Wilmington, Vermont

Early fall view from the top of Mount Olga in Marlboro. — Early fall view from the Mount Olga fire tower.

Mt. Olga is a great day hike for folks visiting Wilmington, which is one of my favorite Vermont towns.

The hike to the top of Mount Olga is one of the easiest summit/fire tower hikes in the state.

Kids will appreciate that they are actually climbing a mountain, but it’s not so hard that it’s frustrating. Still, it is all uphill, so prepare yourself and your kids with an incentive to reach the summit.

If you explore the summit a bit, you’ll find the ruins of the defunct Hogback Ski Resort, which are fun to explore. If you decide to hike the loop without climbing the fire tower, you won’t be treated to the spectacular views, but the woodland trail is still very pretty.

Be sure to catch the view on Hogback Mountain just east of Molly Stark State Park on Route 9.

Easy Hikes in Southeastern Vermont

Now, let’s head east to the Connecticut River Valley. We haven’t done as much hiking in this area, but we’re hoping to add more to this list soon.

Summit Trails on Mount Ascutney: Windsor, Vermont

The view from the top of Mount Ascutney.

There are several hikes up Mt. Ascutney, a beautiful monadnock overlooking the Connecticut River Valley, but if you’re hiking with small children or you want a more relaxing day trip, you can drive right up the mountain to a summit parking area.

Once at the top, the summit trails are easy and fun to explore, with incredible views, a fire tower, and a hang glider launch pad. In fact, Mt. Ascutney is one of the premier hang gliding destinations in the northeast.

There are several trails crisscrossing the summit, but if you want to climb the fire tower and watch the hang gliders, I recommend taking the summit trail to the Weathersfield trail to the hang glider’s trail. The whole loop is about 2 miles.

Putney Mountain: Putney, Vermont

A view of Stratton Mountain from the summit of Putney Mountain / photo credit: Putneypics — photo credit: Putneypics

There is a whole network of trails here, maintained by Windham Hill Pinnacle Association and the Putney Mountain Association.

The Putney Mountain trail is easy enough for families, provides incredible views of the Green Mountains to the west, and is one of the premier spots to watch migrating hawks in the spring and fall.

Once you reach the summit, you can continue on the West Cliff Trail for a longer hike or loop around back to your car for a total of 1.2 miles.

For directions and a detailed trail map, visit Windam Hill Pinnacle Association.

There are many, many trails in and around Brattleboro that I haven’t explored yet. If you have, please leave a comment. I’d love some more recommendations.

Also, the Brattleboro Area Trail System has a fabulous trail map and guide for anyone who wants to explore the area.

Resources for Finding More Southern Vermont Hikes

We hope that Vermont Explored is a good resource for finding hiking trails, but we will never be able to hike and write about them all. So, here’s where we look when trying to find great trails to hike in Vermont.

Hiking in Vermont Facebook Group: This group is very helpful in providing recommendations for trails all over the state and answering any questions you might have about trails.
AllTrails: This hiking trail database includes thousands of trails, maps, photos, and reviews. The AllTrails app allows you to save your favorites, navigate to trailheads, record your tracks, and share reviews. Upgrade to AllTrails+ to download offline maps.
Trailfinder: This is another excellent online database of hiking trails in Vermont and New Hampshire. You can search for trails by location, difficulty level, and activity (snowshoeing, biking, horseback riding, etc.).

Incredible (and Easy) Southern Vermont Hiking Trails for Fall Foliage

Featured Read: AMC’s Best Day Hikes in Vermont

Easy Hiking Trails in Southwestern Vermont