Explore the most popular backpacking trails in Massachusetts with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

Park in the AT/Jacobs Ladder lot on Route 8 & 20, then use the blue connector trail to avoid walking along the road to the AT. Beautiful rolling trail through the woods, fairly easy grades. LOTS of mud currently (mid-Oct). It was a wet day with low cloud; views of the lake were only available once we were right on top of it.

I’m a noob to the AT, but this was the most difficult hike I’ve ever done! If this is “easy” I don’t want to know what a more challenging hike is like. It was beautiful - but tough.

This will become one of my favorite trails. But I don't recommend that you do this after rains unless you have waterproof footwear, as in many places, the trail becomes a brook. Easy hiking in dry weather.

Nice hike! I only did about half of this trek (4 miles total), had two nice views with large rocks to sit on. Took my dog and she liked it as well, there were a few cold streams for her to lay in. Only saw one other couple with a dog, surprised because it was such a nice day. Lots of rocks and ruts so need to be aware of your footing, but I didn't find this hike too difficult. I know it is classified as hard but I think that is a stretch.

Easy trail! love the company!!

hiking
25 days ago

It would be unfair for me to review this trail because it is a part of me. I guess that's the best way to present it. If you choose to walk the full 250+ miles, the trail will absorb a bit of you, and you will absorb a bit of the trail. Follow the white blazes. Bask in the history of America's oldest distance-hike. It is a gateway drug to the Appalachian Trail (which was conceived on the Long Trail, by the way). Get footwear that can withstand comic amounts of mud. This should be on everyone's bucket list.

Grew up hiking these trails with my family!!!

hiking
28 days ago

Quiet trail I thought the trail was relatively easy w a couple of steeper spots , but nothing hard by any means. Stopped at the twisted remains of a plane crash. Then a short push to the AT then we made our way to the summit of Greylock

hiking
1 month ago

The trail was kinda tough to follow, we ended up taking the wrong trail at the weather observatory. Make sure you bring a map with you!

Trail is extremely well marked and maintained! We had a wonderful walk with our dog and 7 year old daughter.

Tough mudder!!

great to go out for a day with the dog

hiking
1 month ago

A very good but looong hike! We parked in the parking lot at Notch road-it looks like the first part of the trail is about 0.3 miles before the start of the trail on the app. I think I saw a sign that said 2.5 miles from the parking lot to the AT. This trail is not very busy which is nice- the plane crash site was interesting to see. We took the AT to the summit of Mt Greylock for some amazing views. There was even a place to buy a meal/snacks/fill up water bottles at the summit. The entire trip from the parking lot to the summit and back was more like 12-13 miles total according to my FitBit.

Beautiful trial a long the Merrimac river. Peaceful

hiking
1 month ago

Beautiful! So much to explore here!!!

The trail is overgrown big time. If you want a claustrophobix hike and practice dodging branches. This is the trail for you.

Signs everywhere saying no dogs! Long drive for nothing ...
Trail is flooded in the first approaching lowland .. not passable

hiking
1 month ago

very crowded on a Sunday morning! started off to the right-trail was good but harder than expected. lots of up and downs before getting to the top of great blue hill. advise going early on weekends. parking lot was completely full when leaving around 1pm.

Wasnt a bad trail. was foggy so views were bad. otherwise would have a bad view. summit was marked by cairn, with some decent outlooks along the way.

Great hike. I parked at Jug End road and began my hike there. Unfortunately I picked a rainy so, it was slippery and muddy, and the trails were covered by the mist. At least it was chilly and not humid or muggy. I originally wanted to hike all the way to Bear Mountain but once I got to Mount Race I decided to go back cause it’s a long loop. If it was a one way, i would’ve done it. A loop hike to Mount Race alone was a total of 12.6 miles and by the time I was close to my car I was so sleepy and hungry lol. I almost wanted to crash at the Glen Brook shelter lol which btw it’s a beautiful shelter. There’s an outback, fire pit, bear box, table with a bench and a creek nearby. I got one clear scenic view but others were misty. The wooden stairs bolted on the rocks are pretty cool too. I was surprised at how many through hikers I met along the way some coming from Maine and others from Georgia. They were real nice people. Other than that, it was an awesome hike.

Trail is very badly marked in several places. The area near the golf course is one of them. Got lost and had to ask some golfers for directions but still a very nice trail overall.

Super fun place to explore! Tons of old foundations, walls and irrigation infrastructure. Wish there was more to indicate what had once been there. Highly recommend giving yourself extra time to explore.

Nice trails, great for hiking or mtn biking.

Walked from redemption rock both ways on the trail.. hilly on the north side of 140 the trail is skinny in some places with a heavy canopy (nice for summer) but well marked. Good for dogs that are leased trained and friendly.. not heavy traffic and surprisingly was not very buggy.

A little grown in, no swimming in the reservoir, the views were very nice. The beginning and end were the best part.

hiking
2 months ago

I'm not sure I've ever been this disappointed by a hike that's received several five-star reviews. I did this as a point-to-point hike with three friends, leaving a car at one end and hiking the 8+ miles from Monroe Bridge to Zoar. Much of the trail is severely overgrown, and a lot of that is fields of grass, meaning that we had to constantly stop to clear ticks off of ourselves before proceeding onward. The initial vista (from the Monroe Bridge side) and final vista (the cliffs overlooking Zoar) were impressive, but the entire plateau in-between was entirely unremarkable. The reservoir itself is surrounded with barbed wire fences, and is situated in a way that there's no way to see it except through a small window in the trees. There were a few raspberry and blueberry bushes along the way which helped to break the monotony of the middle stretch of trail, but I would strongly recommend hiking each end from the river upwards to the vista and back down, rather than hiking the middle section. As a side note, the Alltrails mapping of the trail and the marked route don't match. Near the reservoir, the recording follows the road, not the trail, and a bit further south, the trail isn't actually the Bear Swamp Trail but the recording follows the correct route. This would receive a better rating if only hiked from each end, but not worth the point-to-point distance at all, and definitely not worth a 16-mile round-trip hike.

Fun day and the pond is beautiful. That said, the trail map is poor. We stayed on the AT past the intersection with the Finnerty trail near the pond, and then thought we could go all the way around the pond counterclockwise and back along the eastern edge of the pond, but you can’t do that. Although it looks on the trail map like the Finnerty Trail runs along the edge of the pond and links up with the AT on both sides, it doesn’t. There are dead ends in between and it’s pretty much impassable. There is a way to go around the pond counterclockwise (which we eventually did) but you have to swing wide of the pond to the east.

Also, the trail map makes it look like you can return almost to the parking lot on the Finnerty Trail but you can’t. Finnerty Trail dead ends at Becket Road, and then we had to walk up the pond road, which is steep, to return to the AT. So the bottom line is, this is a nice area to hike, lightly trafficked, and the pond is really nice, but stay on the AT, don’t mess with the Finnerty Trail relying on the All Trails map.

on Cat Rock Loop

walking
2 months ago

Love bringing my dog here. Great place to meet other friendly dogs and walk the trails, let pup swim in the lake

I’m not sure if we went the wrong way but we found this to be mainly flat and were looking forward to elevation; it was steep at the beginning but flattened out and lead to a road with house on it ; didn’t feel like a hike to me: the signs went very clear of where to go either !

Difficult to find where trail begins- parking area is about .2 miles from trail head. If you park in the Appalachian trail/Jacob's ladder lot, there's a .2 mile connection trail, marked in blue, across the road. It intersects the trail in the woods, hang a left. Otherwise you could walk on the actual road for nearly a quarter mile and catch the trail from there- which is why the Alltrails GPS directions will seem slightly off.

Hike is pretty much all uphill for the first half, but is very well covered. You'll also cross another main road on the way. Took us about 1.2 hours to get to the lake- definitely a moderate difficulty. Beautiful view once you're there. Looked like the muddy beginning portion of the hike had been fixed with raised planking. Nearly exactly 3 miles from parking lot to lake. Well marked, took 2 adults about 3 hours to complete out and back at a moderate pace.

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