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Vermont is beautiful in all four seasons, and exploring the mountains and valleys on foot is one of our favorite pastimes. We’ve been trekking and meandering the hiking trails in Southern Vermont with our kids for the past 12 years, and we figured it was high time we share our favorites 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. The best way to encourage my own kids down a trail is with the promise of water for swimming. We’ve got a few more tricks up our sleeves if you’re interested, but a good many of our favorite trails surround lakes, meander along rivers, or end up at the bottom of waterfalls.

More serious hiking opportunities will be covered in another post. Today, we’re going to focus on easy day-hiking in Southern Vermont, including trails in Bennington, Manchester, Stratton, Wilmington, Brattleboro, and Putney.

Easy Hiking Trails in Southwestern Vermont

Lake Shaftsbury State Park, Shaftsbury, Vermont

This 84-acre park is small but well-loved. It is most popular as a picnic and swimming spot for local families, but the trail around the lake is underappreciated and quite lovely. The hike is more of a ramble — a mile in length, meandering through the woods, then wetlands, than 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, your kiddos will want to spend some time on the water, and the beach is the perfect spot for relaxing with a good book. 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.

Difficulty level: easy

Length of trail: 1-mile loop

Kid appeal: swimming, boardwalk through wetlands, decent fishing, boat rentals

Dogs: nope, unless you visit in the off-season

Fee: $4 for adults, $2 for children

For more on this hike, check out: An Autumn Walk Around Lake Shaftsbury

Woodford State Park, Woodford, Vermont

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

Difficulty level: easy to moderate

Length of trail: 2.7 mile loop

Kid appeal: swimming, playground, boat rentals

Dogs: on leash

Fees: $4 for adults, $2 for kids

Want to learn more about Woodford State Park? Check out: Woodford State Park: A Park for All Seasons

Mile Around Woods, North Bennington, Vermont

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. 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 make the adventure last by traipsing across several fields, or by 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 have been meticulously restored and are located behind the main house.

Difficulty: easy for all ages

Length: 1 mile loop

Kid appeal: farm animals, wildflowers, rocks for climbing

Dogs: on leash

Fees: none, unless you want a tour of the historic house

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

Emerald Lake State Park, East Dorset, Vermont

Emerald Lake State Park is nestled in a deep valley between the Taconic Mountains to the West and the Green Mountains to the east. The two mountain ranges are only a few hundred yards apart here, and they rise up steeply on either side of the lake. Covering just 20 acres, Emerald Lake isn’t big, but what it lacks in size it makes up for in beauty. There are several hiking trails in Emerald Lake State Park, and if you and your kids are into vistas, I recommend checking out the Vista Trail, which is a steady climb with awesome views of the lake. I have to say that our kids much prefer the lake trail, which hugs the shoreline, with side trails into the three campground loops. We like taking the trail to the “C” loop because it travels through the wetlands at the south end of the lake, perfect for some kid-friendly birding adventures.

Difficulty: easy, although the campground trail is kind of steep

Length of trail: The lake trail is .5 miles and the campground trail is .4 miles, one way. You can walk back to the beach and parking lot on the campground roads, or turn around and retrace your steps.

Kid appeal: awesome swimming, rope swing for big kids (on the island), bird watching, boat rentals

Dogs: They’re allowed in the campground and on the trails (on leash), but not at the beach or picnic areas.

Fees: $4 for adults, $2 for children

For more about Emerald Lake trails, check out: A Summer in Vermont: Exploring Emerald Lake State Park

Merck Forest and Farmland Center, Rupert, Vermont

Merck Forest and Farmland Center is a nonprofit educational center and outdoor stewardship organization that maintains 3,162 acres of woods and farmland in Rupert, Vermont. There are more than 30 miles of hiking trails to explore, plus cabins for camping. We like to stroll around the farm, visit the animals, check out the maple tap house, and then head up to Birch Pond for a dip and a picnic. This is a fairly easy, 3-mile loop, but we often make a day of it because the animals are so hard to resist.

Difficulty: easy to moderate

Length of trail: 3-mile loop

Kid appeal: swimming, farm animals

Dogs: They are allowed on the trails, but if you want to visit the animals, you should leave your dog at home.

Fees: Free

Read more about Merck Forest here: Cabin Camping at Merck Forest

Hikes for Kids in South Central Vermont

Stratton Mountain Fire Tower, Stratton, Vermont

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 6 miles, round trip. This is a great hike to aspire to, but it’s probably not suitable for young children, unless they are avid hikers already. Luckily, 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, .7 miles to the fire tower, which provides unparalleled views in all directions.

Difficulty: easy

Length of trail: 1.4 miles round-trip

Kid appeal: gondola ride, fire tower

Dogs: No

Fees: It’s $35 for a family of up to eight people to ride up the mountain in a gondola cabin.

The Stratton Mountain Blog has a good overview if this adventure. Check out: Venture Vermont: Stratton Fire Tower Hike

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

Mt. Olga is a great day hike for folks visiting Wilmington, which by the way, is one of my favorite Vermont towns. It’s a 1.8 mile loop to the top of the mountain. Older kids will appreciate that they are actually climbing a mountain, but it’s not so hard that it’s frustrating. Still, it is all up hill, so prepare yourself and your kids with an incentive for reaching the summit. We usually opt for cookies and ice tea. When my kids were little, we would read a chapter of their favorite book at the top. If you explore the summit a bit, you’ll find ruins of the defunct Hogback Ski Resort up here, which are fun to poke around.

Difficulty: moderate

Length of trail: 1.8 mile loop

Kid appeal: ruins, Fire Tower

Dogs: on leash

Fees: $4 for adults, $2 for kids

For more about exploring Wilmington, check out: The Complete Guide to Exploring Wilmington, Vermont

Little Rock Pond, Mt. Tabor, Vermont

Looking for a nice hike to a pristine mountain lake? Little Rock Pond sits just off the Appalachian / Long trail. The hike is 4 miles round-trip, but it gains just 350 feet in elevation. The lake is just far enough from civilization that it is never crowded, but close enough that it can be a nice day trip for a hike, picnic, and swim. Other hikers have seen leeches in Little Rock Pond, but I never have, and we’ve been there dozens of times. Just something to be aware of. There’s a lean-to shelter and several tent platforms set up near the lake for hikers, which also makes this hike the perfect first backpacking adventure for your family.

Difficulty: easy

Length of trail: 4 miles, round trip

Kid appeal: swimming, rock jumping, beaver activity

Dogs: yes

Fees: none, although there is a nominal fee for camping

For a trail description and directions, check out this article in the Castleton Spartan.

Hamilton Falls, Jamaica State Park, Jamaica, Vermont

Jamaica State Park is one of our favorite Vermont State Parks. It includes an awesome rail trail that hugs the West River, which is a gem for swimming. As you hike or bike this trail, you’ll find lots of secluded swimming holes. If you have little kids, I recommend sticking to the West River Rail Trail, which goes all the way to the Ball Mountain Dam. The hike to Hamilton Falls is probably the most challenging on this list. It’s 6 miles round-trip — 2 miles on the rail trail, and then a 1.1-mile climb to the base of the falls. We often shorten our trip by biking the rail trail and then locking our bikes up to a tree while we hike to the falls.

Difficulty: easy on the rail trail, but a steep climb to the falls

Length of trail: 6 miles round-trip

Kid appeal: River swimming, playground, waterfall

Dogs: on leash

Fees: $4 for adults, $2 for kids

For directions and a trail map, check out the Vermont State Parks website.

Hikes for Kids in Southeastern Vermont

Mt Ascutney State Park, Windsor, Vermont

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 criss-crossing 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.

Difficulty: moderate

Length of trail: 2-mile loop

Kid appeal: hang gliders, awesome views, fire tower

Dogs: on leash

Fees: $4 for adults, $2 for kids

Want to read more about Mt. Ascutney State Park, check out: Vermont’s Mighty Monadnock

Black Mountain, Dummerston, Vermont

At 1,280 feet, Black Mountain isn’t huge, but it is an unusual ecosystem for Southern Vermont, boasting lots of mountain laurels and blueberry bushes (ready in late July or early August), and lots of exposed granite. The views are good, but a bit obstructed by trees. When you get to the top, it pays to explore a bit for more exposed outcroppings of rocks and better views. There are two trails up the mountain, from either Rice Road or Black Mountain Road. The Rice Road trail is 1.5 miles and steep. The Black Mountain Road trail is 2.5 miles, but a more moderate climb. Choose the one most suitable for your family.

Difficulty: moderate to difficult

Length of trail: depends – see above

Kid appeal: blueberries, wildlife, good birdwatching

Dogs: no

Fees: none

Putney Mountain, Putney, Vermont

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 awesome 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.

Difficulty: moderate

Length: 1.2 mile loop

Kid appeal: vista, hawk watch

Dogs: on leash

Fees: none

For a 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. As I visit more trails in Southeastern Vermont, I will update this page.

If you’re interested in reading about our favorite hiking trails for kids in Northern Vermont, check out this post: Super Awesome Hikes for Kids in Northern Vermont

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