Hiking with Kids in Southern Vermont
I've been hiking with my kids since they were knee high to a grasshopper, but it wasn't until a few years ago that we started hiking together as a family EVERY SINGLE SUNDAY, year round, no matter the weather.
We've hiked ALL THE HIKES in and around Southern Vermont many times, and I figured it was high-time I pull together a list of my top faves, from east to west, and share them with YOU.
Most of the hikes have been linked up with the AllTrails app, which I recommend downloading to your phone. It'll GPS track your movement, so you'll know exactly where you are at all times. It'll also give you directions, elevation gain, and difficulty level.
That said, I find that MOST times, the difficulty ratings are not entirely accurate. I have a 7 year old and a 13 year old, and we've been hiking these mountains year-round, in all kinds of weather, for YEARS!
I've included a smattering of photos from our years of hiking together so you can see with your own eyes that these hikes are absolutely kid-friendly.
So without further ado... my family would like to introduce you to our favorite local-to-Southern-Vermont hikes!
On the summit of Black Mountain, June 2020.
1. Black Mountain Trail, 3-mile loop, located near Brattleboro, Vermont
The Black Mountain Trail is what my family calls a lollipop-loop, which we MUCH prefer to your typical out-and-back hike. 🍭🍭🍭 When you hike a lollipop-loop, you begin at the trailhead, and hike up the stick. When you come to an intersection, you can go either left or right and hike the lolli-part-of-the-loop. Once you hike the loop, and land back at the stick, you head down the stick, and out to the trailhead.
For this particular hike, we ALWAYS go left when we come to the lollipop-loop intersection, about a quarter-mile from the trail-head. My kids love heading straight for the bog bridges! The trail has a nice "wilderness" feel, even though it's just outside of town. The terrain is easy to moderate, and takes a little umph to get to the summit. Once you get to the top-ish, you'll approach one of my most favorite spots in all of Vermont - a piece of forest that looks like it belongs to a woodland fairy. You'll know it when you see it.
The summit itself is fairly wooded, and doesn't offer up great views, but the summit ledges are pretty darn spectacular, and make for a terrific lunch spot.
The trail down is easier than the trail up, and winds its way past a brook that flows heavily in the spring (but trickles in the summer), alongside a bog that is teeming with frogs and dragonflies, and lands back at the stick of the lollipop loop.
If you're hiking this trail in the summertime, there's nothing better than taking a dip in the West River, which is located just a few yards from the parking lot!
The bog bridges, right at the start of the lollipop loop.
Black Mountain summit in June.
Black Mountain summit in January.
Black Mountain bog in June.
See if you can spot THIS TREE on your descent!
2. Round Mountain - a 2.4 mile out-and-back hike, located in West Brattleboro, Vermont
This super-short hike begins with a trek up a grassy (or snowy) farmland hillside, through some pasture, past an old car cemetery, and then up toward the summit.
We don't hike this one often because we prefer woods walking to pasture walking, but because this one is so close to home, we hold it close to our hearts.
(To get directions, click HERE, and then download the Round Mountain Trail map.)
A view of Round Mountain.
The angle of the hill leading from the parking area makes for a cool photo opportunity!
Round Mountain summit views.
3. Wantastiquet Mountain - a 3.7 mile out-and-back hike, located in Hinsdale, New Hampshire, just over the bridge from downtown Brattleboro
This is what we call the "front side" of Wantastiquet. The OTHER side of Wanntastiquet is equally as popular, and is the highlight of THE NEXT TWO hikes (numbers 3 + 4) I'll share with you!
Wanni (that's what my family calls it) is a local treasure; one that we have hiked AT LEAST 100 times since moving here 13 years ago.
I've carried both of my kids up this mountain dozens of times, and my youngest started hiking this trail with his own two feet starting at around age 1.5. Its easy grade, rhythmic switchbacks, and adventurous shortcuts make this a year-round, any-weather, family favorite, for sure.
Wantastiquet is a SUPER kid-friendly hike!
In the spring, this trail is teeming with newts!
I know this hike like the back of my hand, and will take my kids on this hike alone, without a single worry.
4. Daniel's Mountain / Moon Ledge / Indian Pond - a 4.2 mile loop, located in West Chesterfield, New Hampshire, just over the bridge from North Brattleboro, Vermont
Daniel's mountain is a lollipop-loop hike with great views, Madame Sherri's crumbling castle, varied terrain, a vast lowland bog, and a stunningly beautiful wilderness pond. We've hiked this loop dozens of times, year round, and always find ourselves enamored with how magically the landscape shifts from season to season.
We tend to hike this trail clockwise, which means we visit the castle, traverse the bogs, hit Daniel's Mountain forested summit first, make our way over to Moon Ledge, and wrap up with an easy descent to Indian Pond, before hiking on back to the car.
We especially love this hike in the spring because you'll find bunches of Spongy Oak Apple Galls along the trail! My KIDS love hunting for these mysteriously cool, neon green, roundy galls - MADE BY WASPS - both on the trail AND in the low hanging oak trees!
A map of the area, with the route that we take.
A - B - C - D - E - F - G - H - back to A.
Madame Sherri’s Castle Ruins.
View from Moon Ledge in late May.
View from Moon Ledge in October.
The trail takes you right through a field-of-ferns!
A Spongy Oak Apple Gall
Indian Pond in October.
5. Miners Ledge / Indian Pond - a few mile, out-and-back hike, located in West Chesterfield, New Hampshire, just over the bridge from North Brattleboro, Vermont
This hike starts in exactly the same spot as the Daniel's Mountain / Moon Ledge / Indian Pond hike... but is much shorter, and gives you a pretty darn good bang for your buck.
We start with a quick trip to the castle, traverse the bogs, veer right at the intersection toward Indian Pond, and then begin the steep(ish) ascent to Miner's Ledge.
We do this hike YEAR ROUND, and it never disappoints!
(AN ALTERNATIVE ROUTE - if you're looking for a longer day-hike, you can park a car here on the Madame Sherri side of Wantastiquet, and then park ANOTHER car on the "front side" of Wantastiquet, hike up the 10 switch backs, over the summit, past Miner's Ledge, down to Indian pond, and then out to the parking area. If you look below at the map, you can see the trail.)
A map of the area, with the route we take.
A - B - C - D / D - C - B - A
View from Miner’s Ledge.
More views from Miner’s Ledge.
The trail up is lined with Mountain Laurel in spring!
6. Kilborn Pond, Pisgah State Park - a 4 mile loop, located in Hinsdale, New Hampshire, not far from Brattleboro, Vermont.
When we want to take it easy, and enjoy a leisurely woods walk, THIS is the hike we take. We tend to hike this trail in the fall and winter, but I know for a fact folks LOVE jumping in this lake for a swim, so this is on our to-hike list THIS SUMMER!
Kilburn Pond in early October.
Kilburn Pond in winter.
7. The Pinnacle (via the Holden Trailhead) - 2.8 mile hike (with longer options), located in Westminster, Vermont.
This is hands-down, my favorite hike in Southern Vermont. Its mellow grade, short distance, exquisite views, and summit cabin, make it a top choice when the weather is inclement, or our time is short.
We've done this hike dozens of times, and it NEVER disappoints.
In fact, it has become a family tradition to hike The Pinnacle on Christmas Day, and so far, we've done it 4 years in a row!
We often just hike out and back (see map below: A - B - C - B - A). But if we're feeling a little extra, then we'll turn this into a lollipop loop hike, and travel A - B - C - D - B - A. And if we're feeling EXTRA adventurous, we'll park a car at the Holden Trailhead parking lot, and then drive ANOTHER car over to the Putney Mountain parking lot, and traverse our way from Putney Mountain, over to the Pinnacle!
My kids always LOVE climbing the ladder into the loft of the summit cabin!
Told you we hike Pinnacle in ALL WEATHER! This was Christmas Day, 2018!
Pinnacle in the winter. A place worthy of celebration!
8. Hogback Mountain, a 2.6 mile loop, located near Marlboro, Vermont.
This is a hike we do ONLY in the winter/early spring, because it's short, heavily forested, and has no view. BUT, the dankness of the forest makes for some pretty cool earth-treasures to be discovered if you keep your peepers peeled.
Once we get to the summit area, we usually take off and explore the woods, just to see what we can see, and discover what we can discover.
The trail is usually wet and muddy, so it's one we do in mud boots, for sure.
There are a handful of trail options you can take, so we usually snap a photo of the map located at the trailhead, pick our desired route, and follow accordingly.
A wet, cold summit photo in late March.
When it's hunting season, WE GEAR UP!
One of the coolest mushroom-trees that I’ve ever seen!
Look at this giant mushroom/fungus/blob found traipsing through the woods!
9. Haystack Trail, a 5-mile out-and-back trail, located in Wilmington, Vermont.
We hiked this trail for the first time this year (2020) and I have NO idea what took us so long to discover this beauty!
The trail is mostly gentle (until the last .3 miles to the summit), and the views are incredible. We hiked it in May, when it was still winter in Vermont, so the trail was muddy/snowy in spots, but we managed it just fine in sneakers.
Since I've only hiked it once, I don't have a great FEEL for the mountain... except to know I'd like to hike it 5 more times this year!
Haystack Trailhead
The junction just before the summit.
The views from the summit of Haystack.
Mother's Day, 2020.
10. Harmon Hill - a 3.4 mile out-and-back hike on the AT/LT located near Bennington, Vermont.
If you're looking for a leisurely stroll, this is not the hike for you. This trail is steep, right outta the parking lot. For the first .8 miles or so, you are pretty much going straight up, navigating rocks and roots, twists and turns, and it - is - FUN!
I don't know about YOUR kids, but my kids PREFER difficult terrain because of the THRILL. Sure, they need to take lots of breaks because it's HARD WORK, but you won't hear 'em complaining that they're bored, that's for sure!
Once you get to the top of the steeps, it's all flat from there.
You'll traverse a series of bog bridges through some of the forest's wet spots, before making your way to the Harmon Hill overlook... which is incredibly beautiful, but I don't have a picture to prove it!
Harmon Hill Trailhead (early May)
Bog bridges in early April.
The trail is marked by the world-famous Appalachian Trail white blazes.
Well there you have it, friends! This list should keep you busy year-round, for at least a year! Because I'll tell you what, you could hike the same trail once a month, and every time it'll FEEL brand new! Seasons move fast here in Vermont, so there are always new buds, new leaves, new flowers, new birds, new smells, new wetlands, new bugs, new amphibians to explore and get curious about!
If you're out hiking with your kids, don't be surprised if they're whiney. That's their job. YOUR job is to teach them perseverance, resilience, and tenacity.
Our kids no longer ask us IF we're going to hike on Sunday. They ask us WHERE we are going to hike on Sunday.
It makes me so proud.
Happy Trails!
xo Stasia
