Explore the most popular horseback riding 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.

This is not a moderate trail- the skyline trail as listed above is hard- it’s a long grueling walk from Quincy to the Blue Hill and back. Easily could consume a whole day- I’d advise starting before 9 if you plan to do the entire loop

A ton of stairs, jagged walkways, and numerous spurts of scrambling make doing this entire hike a pretty big challenge.

A bunch of great views- the best of which in my opinion all come from Buck Hill in the middle.

hiking
13 hours ago

Fun, quick up and down. Nice views.

Great trail. The Skyline is a great quick trail for a weekend morning. We had a lovely day and it’s very clean despite the traffic. We did half the skyline trail for a 2 hour hike.

Lots of fun! There are some great views on this trail; however I was constantly surrounded by a group of gnats, so that was annoying.

Easy, sandy, grassy trail that takes you through Nantucket thick brush to open space that is beautiful scenic landscapes. Trail has cool information stops if interested and osprey nest. Fun 3 miles trek out to ocean and 3 mile back through natural unblemished Nantucket views.

hiking
4 days ago

This was marked by someone who has never hiked. I don’t have any other explanation. The first time I went around I got off trail about 4 times I had to backtrack and by the end lost the trail completely, ended up on someone’s driveway and took that out. I thought I could go the opposite way to see where I went wrong and instead ended up taking a big circle back to the parking lot.
I have been hiking for over 30 years and never had a more frustrating experience than this loop. The blue seems what you follow when you start and then the yellow comes out of nowhere. There are probably 50-100 trails that branch off for access from peoples homes.
I wanted to love this because it’s so close to home but it’s awful and I’ll only ever go back for kayaking.

Nice, easy trail with a few hills involved. Not much access to the pond but i did find an area for the dogs to take a dip. Didn’t see many people on the trail. Bring bug spray!

trail running
6 days ago

Kudos to the folks that take care of this place. The blocked trail from the fallen tree has been cleaned up. No overgrowth. Great for trail running with the pup.

I definitely enjoyed hiking here. lots of nice trails to explore

Beautiful place to walk around and enjoy, the views of the Boston skyline are pretty amazing and I’m pretty sure its safe to swim in some parts. The only downside is it’s not free

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.

Fun for kids!

If you feel as though you aren’t seeing marks on the trees, don’t worry, keep looking...especially if you see many fallen trees around!

You can easily spend the entire day on this trail. Many difficult slopes and interconnecting trails. I cast my vote to categorize this trail as 'Hard'.

Excellent hike. Great view from the peak.

Easy hike. The trail is beautiful, met quite a few people with off-leash dogs along the way, all very nice and friendly. There was a kids camp there as well so pretty busy, especially for a weekday. But beautiful area, easy, scenic hike. And very dog-friendly but make sure your pup is ok with meeting dogs because there are a lot of them here!

Nice trails, great for hiking or mtn biking.

hiking
18 days ago

Trail isn’t marked. Difficult terrain, not well maintained.

Nice wide and well marked trails. The woods were nice but the view at the peak was nothing special. It was a nice afternoon walk in the woods!

Awesome

hiking
19 days ago

This is a scenic and well-marked trail but unfortunately I had to turn back as I was swarmed by bugs despite multiple applications of 30% deet bug spray. Will return in a cooler, less buggy season.

walked this trail many times, easy to get to, easy to walk, great place to talk your dog.

Well kept trails, great variety of terrain, dotted with ponds. Be sure to take a map! So many trails, you can make it a different hike every time.

25 days ago

One of our favorite places to take the pups - gorgeous!!

hiking
26 days ago

Nice hike for the full day, very rocky indeed! We liked the view of Boston skyline at the top of the hills. We saw a really big snake, a deer, and on our way back heard some other animal roar and just ran along the trail to get away from that spot ASAP:) it was getting darker though, so I guess that’s why animals were coming closer with almost no people on the trail. So definitely a great trail, but better go in the morning-early afternoon to get back before dark.

Lots of fun to climb, really a steep start, but the views are worth it. Parking was kind of far away

29 days ago

Far too many dogs off leash. Rules need to be followed whether you agree or not. I shouldn't be deprived of walking a beautiful trail because people can't follow a very simple rule.

This is no doubt a difficult trail: we kept joking that it goes uphill both ways , because it goes up and down a lot weather you’re going in or out. There’s a LOT and difficult areas with big rocks , this is definitely not for beginners or anyone with injuries : you could shorten it to any length you want because it is a loop you can just turn around when you’re halfway to what you want to do’ we did this in preparation for the Spartan Beast and it was a great workout with challenges !

The initial push up the hill can be a tad bit tricky, but nothing anyone can't handle. Big rocks to climb over and plenty of roots in some sections. Overall, I really nice hike and it wasn't too busy when we went.

It was cool to see all the bunkers but the bugs were literally out of control. I would recommend going when some bugs have died for the season...

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