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Get Outside: The Best Hiking in Southern Vermont

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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 15 years, and we figured it was high time we share 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.

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, but first a few logistics.

When is the best time to hike in Southern Vermont?

We hike the trails in Southern Vermont year-round, so don’t let the temperature discourage you. Our favorite time to hike in this area is early October because the fall colors are incredible, but fall is also prime tick season, so be sure to protect yourself from those nasty critters.

Summer is our second favorite time to hike in Vermont. The days are long, the weather is warm, and we can cool off with a swim during or after our hike. The trails are busiest in the summer, but even on the most popular trails, there’s plenty of room to spread out.

Finally, all of these trails are totally doable (and beautiful) during the winter months. You made need to bring a pair of snowshoes or microspikes, but because these trails are pretty short, you should be able to accomplish them without issue.

What to Wear Hiking in Southern Vermont?

Layers! It doesn’t matter what time of year you’re hiking in Southern Vermont – layers are your friend. Here’s what I wear when hiking Vermont trails.

  • Hiking pants – I recommend hiking in long pants, even in the summer. Lightweight pants will keep the bugs away and will also protect you from brambles and poison ivy. My current favorites are these straight leg hiking pants from Columbia because they come in short sizes. Eric wears these Quandary pants from Patagonia.
  • Hiking tights – For cooler temps, layer a pair of leggings or tights under your hiking pants. These amazing leggings are lined with merino fleece and can be worn with our without hiking pants throughout fall and winter.
  • Wool socks – Wool is my favorite fabric for hiking year-round. I wear Darn Tough Vermont wool socks in the summer and winter. I love that they are made in the USA and that they come with a LIFETIME guarantee. They come in sizes for men, women, and kids.
  • Wool top – Guess what? I’ve found the softest wool layers for hiking. They are made by Woolx and they wick away moisture, dry fast, and can be machine washed. The best part is they keep you cool in the summer and warm in the winter. And no matter how much you sweat, Woolx shirts don’t stink! Woolx makes short-sleeve, tanks, and long-sleeve tops form both men and women.
  • Puffy layer – A lightweight puffy jacket is indispensable. They are incredibly warm and they pack up very small. I wear mine all winter and keep it in my daypack in the summer and fall, just in case. My favorite down layer is from Patagonia and has lasted many years.
  • Waterproof layer – A packable raincoat is useful for Vermont’s unpredictable weather. We pack the men’s and women’s versions of the Ranier Rain Jacket from REI Co-op. I recommend going one size up from what you normally wear so you can layer it over your puffy if you have to.
  • Hiking shoes – Vermont is a rocky, rooty state for hiking. I recommend sturdy hiking shoes over trail runners or sandals. I love my Oboz Sawtooths because they have a narrow heel and a wide toe box, but as long as they’re sturdy, bring whichever brand works best for you.

Resources for Finding Great Southern Vermont Hiking Trails

We hope that Back Road Ramblers 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 – The people in this group are so helpful at providing recommendations for trails all over the state and can answer any questions you might have about trails.
  • AllTrails – This hiking trail database includes thousands of trails, as well as maps, photos, and reviews. You can save your favorites, navigate to trailheads, record your tracks, and share reviews all within the AllTrails app. So useful!
  • Trailfinder – This is another great 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.).

Easy Hiking Trails in Soutwestern Vermont

Southwestern Vermont is our home turf, so we have lots of suggestions for hiking in Bennington, North Bennington, and Shaftsbury.

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
An autumn view from the beach at Lake Shaftsbury State Park

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 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, 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, a boardwalk through wetlands, decent fishing, boat rentals
Dogs: on-leash, but not on the beach or picnic area
Fee: $4 for adults, $2 for children

For more on this hike, check out Lake Shaftsbury State Park in all Four Seasons.

Woodford State Park: Woodford, Vermont

An image of two children running through the water at Woodford State Park. Best hikes for kids in Southern Vermont.
After hiking around Adams Reservoir in Woodford State Park, be sure to make time for a swim.

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

A shot of a huge sugar maple in North Bennington, Vermont
This is my favorite tree – Mile Around Woods, North Bennington

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

The view from the lake trail in Emerald Lake State Park
The view from the lake trail in Emerald Lake State Park

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

A lone birch tree on the farm road in Merck Forest. Best hikes for kids in Southern Vermont.
Merck Forest has one of the most extensive trail networks for hiking in southern 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

Easy Hikes in South Central Vermont

The Green Mountains runs 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!

Stratton Mountain Fire Tower, Stratton, Vermont

The view from the top of Stratton Mountain, showing the gondola and wildflowers
A view from the top of Stratton Mountain / photo credit: Hubert Schriebl

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

A sign for the trailhead to Mt. Olga
The trailhead to Mt. Olga in Molly Stark State Park

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 uphill, 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

Two boys dive from a cliff into the waters of Little Rock Pond in Vermont
Cliff diving at Little Rock Pond/Photo credit: Joseph Bylund

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 is 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

The lovely Hamilton Falls in Jamaica State Park

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

Read Next: 7 Memorable Things to do in Jamaica State Park

Easy Hikes in Southeastern Vermont

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

Mt Ascutney State Park, Windsor, Vermont

The summit trails at the top of Mt. Ascutney in Vermont
The summit trail in Ascutney State Park

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

A wooded view of the summit of Black Mountain. Best hikes for kids in southern Vermont
The summit of Black Mountain in Dummerston / photo credit: Place UVM

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

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


Looking for more opportunities to hike in Vermont? Check out our Vermont Vacation Guide for Outdoor Lovers or read these posts:


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Our Favorite Resources for Road Trips and Outdoor Adventures

These are the resources we use for planning road trips, saving money while traveling, and shopping for outdoor gear. 

Car Rentals: While we use our own car most often for road trips, we also enjoy flying into major airports and then renting a car for more regional road trips. We use Kayak to compare prices and find deals from dozens of car rental agencies at once. 

Flights: We use Kayak or Skyscanner to search out flight deals. Money-saving tip: If you find yourself using the same airline over and over again (we are huge Southwest fans), consider joining their loyalty program and getting an airline credit card. With our Southwest Rewards Visa, we earn a few free flights each year. 

Hotels: When it comes to lodging, we seek out small boutique hotels or quirky roadside motels. First, we search for hotels on TripAdvisor so we can read reviews from other travelers. Then, we use Booking.com to make reservations (they have the best prices, plus a flexible cancelation policy).

Camping: Camping is one of our favorite things to do on long road trips. It allows us to explore the outdoors, cook our own food, and save money. We use They Dyrt Pro to find campsites and read reviews before booking on Recreation.gov or state park websites. 

Glamping and Vacation Rentals: For weekend getaways and shorter vacations, we love glamping (check out our glamping resource guide). We book glamping properties through Tentrr, Hipcamp, and Airbnb. For cabins and vacation rentals, we like to use VRBO (they have fewer fees and a better cancelation policy than Airbnb).

Guides and Maps: If we are visiting a new region, we usually invest in a Moon Travel Guide for the area. We pass them on to friends and family after our trip.  If we are planning on hiking, we also purchase a Falcon guide in the Best Easy Day Hikes series.

Outdoor Gear: We are REI Co-Op members. It cost us $20 for a lifetime membership, but we get a yearly dividend based on our purchases, plus great deals and coupons throughout the year. REI also has a great return policy.

Check out our complete guide for planning a road trip on a budget

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