Family Friendly Hikes Around New England
view from the top of Table Rock in Grafton Notch State Park in the summer
Looking for a mountain to get your family into hiking? This is our working list of hikes we’ve experienced, separated into five of the six New England states. (Sorry, Rhode Island, we haven’t found a mountain there yet!)
These hikes are perfect for getting the entire family outdoors. They all have pretty views, nothing on this list is too challenging, and each one will leave you feeling accomplished and happy because you just spent time in nature.
Our Family-Friendly Rating Scale-
We rate hikes on a 1–5 scale, with 1 being the easiest and 5 being the most challenging. No two families, mountains, or hikes are the same, so think of this as a guide rather than a rulebook. Each listing includes our 1–5 rating, mileage, elevation gain, and whether it’s a good spot for your four-legged family member.
5 – Advanced Family-Friendly
These hikes can be around 5 miles (sometimes less). They’re not for first-timers. They’re for families ready to tackle a bit more length, elevation, and challenge. You might be a little out of breath and sore the next day, but you’ll earn both the view and the workout. Some of these could have a bit of basic rock scrambles, but nothing you can’t handle if you’ve hit the trails before.
4 – Upper Moderate
Not quite advanced, but definitely a step up from a moderate hike. These trails have views, elevation, and miles (usually under 5). Consider these when you’re ready to move up from moderate hikes but not quite ready for the advanced challenge.
3 – Moderate
These hikes are around 3 miles or less with enough elevation to give you a workout and views to match. Perfect for when you want an adventure but still have plans later in the day. You’ll get your nature fix without being gone for hours.
2 – Easy
Great for starting your family hiking adventures! Ready to break in those hiking boots or get your younger kids some trail experience? These are perfect starter trails, maybe a bit longer or steeper than a “walk in the park,” but still very approachable.
1 – Super Easy
Kind of like a walk in the park (literally). Not sure how your kids will do on a mountain? Start here.
You know your family best! Always bring water (and maybe a snack or two). Nobody wants a hangry hiker! Stay safe and have fun!
Vermont Hikes
Mt. Philo
Rating: 2 Location: Charlotte, VT Miles: 2 Elevation Gain: 652 ft Dog-Friendly Bathrooms at trailhead
A beautiful hike with some stairs and great views from the top! Plus Adirondack chairs where you can relax and take in the Adirondack Mountains.
Gile Mountain
Rating: 2 Location: Norwich, VT Miles: 1.5 Elevation Gain: 387 ft Dog-Friendly No Bathrooms
A fairly short hike with lots of stairs and a cool fire tower at the summit. On a clear day, you can even spot the ski trails of Killington Mountain.
Mt. Pisgah
Rating: 5 Location: Orleans, VT Miles: 4.5 Elevation Gain: 1,660 ft Dog-Friendly No Bathrooms
The most challenging on our Vermont list due to length and elevation. The viewpoints are stunning! Watch out for cliffs!
Maine Hikes
Mount Agamenticus
Rating: 2 Location: York, ME Miles: 1.5–2+ Elevation Gain: 350+ ft Dog-Friendly on a leash Bathrooms at the trailhead and peak
A perfect first mountain for little hikers. There are a variety of trails here, choose your own adventure! You can make it short and sweet or extend your outing as you wish. On a clear day you can see Mt Washington and the Atlantic Ocean!
Table Rock
Rating: 3 Location: Gilead, ME Miles: 2.3 Elevation Gain: 902 ft Dog-Friendly Bathrooms at the trailhead
You can take the loop counterclockwise for the steep section first, or clockwise to avoid it and do an out-and-back. Either way, you’ll earn those views. The steep rocky part has serious fairytale vibes, beautiful and a bit breath-stealing (in both senses!).
Views from the peak of Table Rock in Grafton Notch State Park
Mt. Philip
Rating: 1 Location: Rome, ME Miles: 1.4 Elevation Gain: 338 ft Dog-Friendly No Bathroom
A short and lovely hike. No sweeping views, but a wonderful family trail for kids and dogs alike.
When the leaves are off the trees you get pretty views at Mt Philip
Mt. Megunticook
Rating: 3 Location: Camden, ME Miles: up to 4.5 (can be under 3) Elevation Gain: 1,214 ft Dog-Friendly Bathroom at the trailhead
Choose your adventure! Some solid elevation may leave you catching your breath, but on a clear day, the views of Camden Harbor are worth every step. You can even extend your trek over to Mt. Battie. (Sure, there’s a road to the peak, but hiking it is way more fun and that’s what this list is all about!)
Mt Megunticook on a cloudy day
New Hampshire Hikes
Mt. Major
Rating: 4 Location: Alton Bay, NH Miles: up to 4.5 Elevation Gain: 1,165 ft Dog-Friendly Bathrooms at trailhead
A very popular hike, and for good reason. Depending on the trail you choose, you might find yourself scrambling over rocks or taking a longer but gentler route. Either way, the views of Alton Bay are stunning.
Hazy views from our end of summer hike of Mt Major
Mt. Monadnock
Rating: 5 Location: Jaffrey, NH Miles: 3.9 Elevation Gain: 1,772 ft Dog-Friendly Bathrooms at trailhead
One of the most hiked mountains in the U.S., and for good reason. It’s a true New England classic. But don’t underestimate it just because it’s popular! Bring plenty of water and snacks; this one is a workout.
Mt. Pemigewasset
Rating: 5 Location: Franconia Notch State Park, NH Miles: 3.5 Elevation Gain: 1,260 ft Dog-Friendly Bathrooms at Flume Gorge on season only
A fun family challenge with rewarding views at the top. We even tackled this one as a winter hike, it was a great way to test our gear!
Mt Pemi is even a fun winter hike!
Mt. Willard
Rating: 3 Location: Twin Mountain, NH Miles: 3.2 Elevation Gain: 912 ft Dog-Friendly Bathrooms at trailhead and AMC Hut
A personal Around New England favorite. It’s a steady climb to the summit, with stunning views of Crawford Notch. Pack snacks and water, there’s no better spot for a mountaintop picnic.
Mount Kearsarge
Rating: 4 Location: Winslow State Park, Wilmot, NH Miles: 2.5 Elevation Gain: 1,115 ft Dog-Friendly (on leash) Bathrooms at trailhead
Bathrooms at the trailhead (always a plus). There’s a small fee unless you have the NH State Park plate. The loop trail can be hiked either way. Go counterclockwise to tackle the steep part first and save your knees on the way down. There’s even a tower at the top you can spend the night in (first come, first serve)! A great family hike with a little challenge and a big payoff.
Massachusetts Hikes
Mt. Tom
Rating: 2 Location: Holyoke, MA Miles: 1.5+ Elevation Gain: 627 ft Dog-Friendly No Bathrooms
A fun, fairly short hike with a few steep sections and some loose rocks. There are multiple trail options, so you can make it longer if you’d like. A great family spot if you’re in the area.
Connecticut Hikes
Ragged Mountain Preserve
Rating: 2 Location: Berlin, CT Miles: up to 4.5 Elevation Gain: 620 ft Dog-Friendly No Bathrooms
A peaceful and beautiful hike with more trail than parking — the lot is small! You can take a shorter route, but if you want those great views, be prepared for a bit of a longer trek. Some steep sections at the start, but totally worth it once you reach the top.
Always stop and enjoy the views! Ragged Mt Preserve has some beautiful spots!
We will keep adding hikes as we experience them and think they would be good for the entire family! If you have any we should check out please let us know! Happy Hiking!
52 With a View Hiking list
New Hampshire 52 with a view our list as we work on it and our ratings for views and difficulty.
When my hiking journey began 20+ years ago, my dad and I had one goal for every hike: great views and a little challenge—but not so hard that we’d be limping into work the next day. We used to search through a book called Foghorn Outdoors New England Hiking: The Complete Guide to more than 380 hikes by Michael Lanza, where the author rated trails 1/10 for both views and difficulty. And so, our quest began.
Little did we know about the 52 with a View list back then.
When Mike and I started hiking more, we also had goals—maybe we’d tackle the 48 4,000-footers one day. But before diving into those bigger challenges, we wanted to get our hiking legs under us. So, we set out to find hikes that checked the boxes: beautiful views with some challenge… but not 4,000-footer-level challenging—yet.
Enter 52 With a View
A friend eventually introduced me to Ken MacGray’s book: New Hampshire’s 52 with a View: A Hiker’s Guide. This list was originally created by the Over the Hill Hikers Club in 1990. Apparently, it took me a while to catch on! We love having a list of mountains with great views!
Funny thing? We’d already hiked some of these mountains before we even got the book! Now, we’re thrilled not to have to scour the internet for hike suggestions anymore.
In 2024, we officially started checking off these beautiful spots. In this blog, we’ll tell you all about each one, updating the list as we go.
Mt. Willard
We conquered Mt. Willard on July 4, 2024. It was a warm, beautiful day. We hit the trail early, and I’m so glad we did because that parking lot is happening! There are multiple trailheads in the area, and since it was a holiday, we knew it would be busy.
The trail itself is pretty easy—no rock climbing or scrambling, just good ol’ fashioned hiking. The views along the way are lovely, especially when passing Centennial Pool.
Rating:
🌄 View: 10/10
⛰️ Difficulty: 3/10
Family & Dogs: Dogs on a leash are cool. This would be a great hike for families with kids!
Location: Crawford Notch
Distance: 3.1 miles round trip
Elevation Gain: 895 ft
2. Mt. Cardigan
Another July hike for us—and I’m so glad we stumbled upon this one! It was a great hike with some steep sections. You can listen to our podcast where Mike talks about how he wasn’t sure he was going to make it off the mountain… spoiler: he did, and he’s fine.
There’s a loop section here, and if you know us, you’ll know we somehow got lost… not sure how that happened, but we made it! And, bonus: we took the correct way down. FYI, anytime we’ve gotten lost, it’s because we didn’t have the AllTrails app yet. Don’t make the same mistake we did—get the app. It’s a game-changer.
Anyway, back to the hike! It was a steady climb to the summit, and the views from the top were more gorgeous than I expected. There’s a fire tower at the summit that wasn’t open when we visited, but if it’s staffed, you can climb up, learn about fire spotting, and enjoy even more amazing views.
Rating:
🌄 View: 10/10
⛰️ Difficulty: 3.5/10
Family & Dogs: A little more challenging than Willard but doable for kids who aren’t afraid of heights. Dogs are welcome as long as they’re on a leash.
Location: Cardigan State Park, Orange, NH
Distance: 3.1 miles round trip
Elevation Gain: 1,194 ft
3. Mt. Chocorua
This was one Mike and I had both done before—just never together. I was so excited to show him the Brook and Liberty Trail, which is absolutely beautiful and never seems to be busy when I go. But this particular day? If you’ve listened to our podcast, you already know—it was a very challenging hike for me. If you want to hear all about my struggles, go check out that episode. Spoiler alert: I’d do this hike again in a heartbeat because it’s amazing.
As of writing this, I haven’t completed the 52 With a View list yet, but Chocorua was by far the most challenging for me. If you choose the Liberty and Brook Trail, I recommend hiking it clockwise. You’ll follow a stream for most of the way up, and I highly recommend doing this in the fall. The colors are breathtaking. Have I mentioned how amazing it is?
Rating:
🌄 View: 10+/10
⛰️ Difficulty: 8/10
Family & Dogs: I saw families with older kids, maybe middle school and up. This isn’t to say younger hikers couldn’t do it, but I’d only recommend it if your child has hiking experience. Definitely not a beginner hike. You know your kids best, but this is not one I would have brought my daughter on when she was younger.
Location: Albany, NH
Distance: 7 miles round trip
Elevation Gain: 2,582 ft
Mt Kearsarge on a cloudy day
4. Mt. Kearsarge
This wasn’t our first time hiking Kearsarge, but it was the first time we were disappointed by the views. No fault of the mountain—it was just one of those cloudy days.
We did the loop here (no getting lost this time—win-win!) and went up Winslow and down Barlow. It was definitely a relentless climb up, but overall, a beautiful hike. There are some big rocks to step up, but nothing too challenging. You can find out why we hiked the day we did and other details of the trail HERE on our podcast.
Rating:
🌄 View: 3/10 (blame the clouds!)
⛰️ Difficulty: 3/10
Family & Dogs: Popular hike for families, and dogs are welcome on a leash. A little more challenging than Willard, but if your kids are up for a fun adventure, this is a great mountain to tackle.
Location: Winslow State Park (fee required unless you have the NH State Park plate)
Distance: 5.7 miles round trip
Elevation Gain: 2,565 ft
One of the famous caves on Morgan & Percival
5. & 6. Morgan & Percival
I’ll admit—I was skeptical about this one. I mean, how many pre-hike Google searches include “Will I fit in the cave?” or “How sketchy are the ladders?” Or worse… “Has anyone died in the cave?”
Let me put your worries at ease—none of my crazy Google searches came true. The caves are avoidable if you pay attention, and the ladders felt totally safe… even if we went down instead of up. Yep, you guessed it—we went the wrong direction. It’s recommended to go clockwise, but we somehow went counterclockwise. You can listen to the podcast episode where we recount that adventure!
Fun fact: This double-peak hike counts as two spots on the 52 With a View list. And with a loop, you’re already committed—might as well do both!
Rating:
🌄 View: 7/10
⛰️ Difficulty: 7/10
Family & Dogs: Yes, families ready for adventure and dogs on a leash are welcome!
Location: Holderness, NH
Distance: 5.5 miles round trip
Elevation Gain: 1,522 ft
7. Middle and North Sugarloaf
Only Middle Sugarloaf makes the official 52 With a View list, but honestly, do both. The trail looks like a sloppy capital “T” if you were looking at it from above. We went right first to conquer North Sugarloaf and then headed to Middle Sugarloaf.
The views from both peaks were stunning, even on a cloudy morning. The trail starts pretty steep—no breaks until you get to the top of the “T.” You’ll also find some cool glacier boulders, a staircase, and even a cold plunge spot at the end. Honestly? It’s a pretty magical place. Listen to more details about this hike HERE on our podcast.
Rating:
🌄 View: 9/10
⛰️ Difficulty: 5/10
Family & Dogs: Great spot for the whole family, and leashed dogs are welcome.
Location: Bethlehem, NH
Distance: 3.5 miles round trip
Elevation Gain: 1,059 ft
8. Welch & Dickey
Another two-for-one deal in a loop! We hit this one at the peak of fall foliage, and if you can time it as perfectly as we did—do it! The views and the trails here are pure magic.
We hiked counterclockwise (and actually followed directions this time—thanks, AllTrails!). The hike starts off with a gradual climb but eventually gives you a solid cardio workout. Once you hit Welch, you can see the peak of Dickey, and while it looks intimidating, it’s not as bad as it seems. You can listen to more details about this hike on our Welch & Dickey episode.
Rating:
🌄 View: 10/10
⛰️ Difficulty: 7/10
Family & Dogs: Yes to both, as long as your dog stays on a leash. It’s a bit more challenging due to the length, steepness & a little bit of rock climbing, so gauge what your kids are up for.
Location: Waterville Valley, NH
Distance: 4.4-mile loop
Elevation Gain: 1,781 ft
9.Mt. Pemigewasset
This was our first winter hike, and I fell in love with winter hiking. I mean, if we live in New England, we might as well embrace the never-ending winters, right?
It was the perfect hike for everything to go wrong too… not really, but when you start by locking yourself out of your car, it’s a tough beginning. You can listen to all that drama (and how well we handled it) on our podcast.
We parked at the Flume Gorge—if you’re visiting during the busy season, get there early or plan accordingly because it’s a very popular spot. The trail was gorgeous and not overly challenging. In winter, there was no rock scrambling, but there were some steep parts. I loved the vibe here and would definitely like to check it out during a different season.
Rating:
🌄 View: 9/10
⛰️ Difficulty: 5/10
Family & Dogs: Dogs are welcome as long as they stay on a leash.
Location: Franconia Notch State Park
Distance: 3.3 miles out and back
Elevation Gain: 1,259 ft
Mt. Roberts with views of Gunstock Mountain
10. Mt. Roberts
Hiked on March 26, 2025—just three days after a surprise spring snowstorm. There was no snow left at home, but we came prepared for whatever the trails had in store.
The adventure begins the moment you pull into the parking area for Mt. Roberts. You’re immediately greeted with views that make you question if you even need to hike. (But trust me, you do!) The trailhead is located near Castle in the Clouds, which, unfortunately, was closed for the season.
The Hike:
The trail itself was fairly easy, with a slow and steady incline that offered plenty of opportunities to pause and soak in the scenery. And the views? Pretty much nonstop—especially if you remember to look behind you! About halfway up, there’s a scenic lookout point that’s well worth a quick break.
Now, here’s where Mt. Roberts likes to play tricks on you. A few times, you’ll think you’ve reached the summit… but nope, not quite! The actual peak isn’t the most dramatic, but it rewards you with stunning views of the White Mountains.
The Descent:
On the way back down, we stopped for lunch on a rock slab with breathtaking views of Lake Winnipesaukee and Gunstock Mountain. It was one of those “this is why we hike” moments.
Location: Moultonborough, NH
Family & Dogs: Great for families and dogs on a leash
Distance: 5.2 miles (though my watch begged to differ and clocked a bit more)
Elevation Gain: 1,335 feet
View Rating: 🌄 10/10
Difficulty Rating:⛰️3.5/10
11. Mount Monadnock
Checked off in April on one of those rare, perfect spring days—bluebird skies, no ice, and surprisingly warm weather. Monadnock is one of the most climbed mountains in the U.S., and now we understand why. Mike did this one solo because G was away and she had done this one several times before.
The Hike: He took the White Dot Trail up and came down via White Cross—a great combo if you prefer scrambles on the way up and something gentler on the knees for the descent. White Dot gives your legs and lungs a good workout, and there are a few hands-and-feet scrambles near the top. Not technical, but enough to make you earn those summit views.
The summit delivered 360-degree views into Massachusetts, Vermont, and the Whites. It’s a rocky, scrambly, beautiful hike that’s more of a challenge than its popularity suggests. Bring plenty of water, good shoes, and a sense of humor for the scrambles. Pack sunscreen and bug spray, and swing by the cute trailhead store. Bonus: the bathrooms have real plumbing!
Rating:
🌄 View: 10/10
⛰️ Difficulty: 6.5/10
Family & Dogs: We saw plenty of families—some kids were crushing it, others not so thrilled about “too many rocks.” Dogs are welcome, but make sure they’re comfortable with rocky terrain.
Location: Monadnock State Park (reservation recommended; $15/car or free with NH State Park plate)
Distance: 3.9 miles loop (White Dot up, White Cross down)
Elevation Gain: 1,772 ft
12. Mt. Cube
We hiked Mt. Cube on a beautiful Friday in late June. This spring made it tough to plan hikes around the rain, but on this particular day, we got lucky. The weather was perfect—not too hot—which felt like a win considering it had been over 100°F just a few days earlier. (If you're more of a listener than a reader, you can catch all the details on our podcast!)
Mt. Cube is located in Orford, NH—a part of the state I hadn’t heard of before. To get there, we took Exit 26 off I-93 North in Plymouth. That section felt familiar, but once we left Plymouth, things quickly got more remote. Mt. Cube is about 25–40 minutes from Plymouth, depending on your pace.
Pro tip: Hit the Dunkin’ in Plymouth before you head out—it's your last public bathroom stop!
The parking area is a small lot, and the trailhead is just a short walk down a dirt road. We took the CRT (Cross Rivendell Trail).
The hike itself wasn’t super challenging, in my opinion. It had a steady incline with some breaks along the way. Near the summit, there’s a great spot to rest and take in the views. Mt. Cube actually has two peaks. The South Peak is about 4.2 miles round trip, and if you add on the North Peak, your total hike will be around 5 miles. Both are worth seeing! The South Peak is the one that counts for the 52 With a View list. The North Peak isn’t hard to reach, though we did get just a tiny bit turned around—as usual.
Rating:
🌄 View: 9/10
⛰️ Difficulty: 3.5/10
🐾 Family & Dogs: A great hike for families—and dogs on leashes! I found it to be easier than Mt. Cardigan and Mt. Willard.
Quick Info:
📍 Location: Orford, NH
🥾 Distance: 4.4 miles round trip
📈 Elevation Gain: 1,600 ft
Almost to the summit of MountChocorua
Whew, that’s a lot of views—and we’re just getting started! Stay tuned for more as we continue to check off the list! 🥾🌲