Explore the most popular hiking trails near Quincy 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 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.

hiking
15 days ago

Super rocky and not my favorite. Struggled with signage above the skyline. Narrow areas where I felt super nervous I would fall and hurt my ankles. Hiked in the late afternoon and would recommend hiking earlier so as to not feel pressured. Took a detour for an overlook and hiked over 7.6 miles. Not sure I would hike this same trail again.

Should definitely be rated as strenuous. Mostly steep ups and downs with scattered, lose rocks. Only a few sections have rock stairs. Also my tracker said it was 13.7 miles not 11.9. Regardless of its challenge, the Skyline Trail is the most beautiful and exciting way to experience Blue Hills . It traverses all the best hills, most have views and some have open panoramic views. On a clear day you can see Boston and the ocean. Very easy trail to follow, just look for the blue blazes. Certainly worth the effort and I would definitely hike it again.

Good trail, good views even on a cloudy day. The dog and I had a blast! It is definitely rocky so be prepared, Stop by the visitors center before you start to get your bearings and advice on where to start, they were very helpful.

This trail is a good hike up. I love that it’s close by, easy access, can sometimes be a pain with parking on busy days. I like the option of climbing over rocks and a more adventurous ways up and down the mountain. Also good for strollers or elderly, with a paved path to walk up to. The hike up will make your blood pump, and be a decent work out.

moderate to difficult, very rocky

Gnarly rocky and rooty. If you’re not going up you’re going down or just about to do one or the other.

Not mind blowing or remote, but honestly, this is so great considering you're still in metropolitan greater Boston. There is some great elevation change and wonderful views. And 6 miles is 6 miles.

Beautiful views, great workout over up and down rocky trail. Not for a beginner. The right shoes (hiking boots) make all the difference.

This is an awesome not so trafficked trail, making you feel like you’re hiking in a remote area until you reach one of the small summits and see the city skyline reminding you’re not far from Boston at all.

Love this trail. Amazing views, and a great hike if you decide to do the whole trail.

hiking
2 months ago

A very rocky trail that will get your heart pumping. The trail is very well marked. I felt that if I was ever in doubt of the path direction I could be confident that if there was a choice between a smooth path or a rocky path the correct choice would always be the rocky path. The views at the top of the hills are not spectacular enough to put up with dealing with the constant rockiness.

Quick and easy...great views!

hiking
2 months ago

This trail should be rated hard. It is very very rocky and has many steep grades both up-and-down. It is beautiful but can be challenging. It felt more like I was rock climbing then hiking on many parts of the trail. It is much harder then another trail I took that is rated hard. I'm not sure who does these ratings. A trekking pole would have helped me on this hike.

Great hike and really fun in Spring. If you do the entire round trip, it's 3,160 feet of elevation. Not a moderate hike. How Wolcott gets rated hard, when it's no where's near as long or difficult is beyond me.

Parked on Randolph Ave and headed up Hawk Hill. Continued easterly to Barberry Bush Trail and the Great Cedar Swamp. Bushwacked a bit over to the direct route up Kitchamakin Hill. Turned westerly over Fenno Hill to Chickatawbut peak. Continued by the Education Center then headed down the Skyline Trail back to my car. This is a terrific trek and property. Just do it!

This was my first time at Blue Hills. It’s beautiful! While not all of this trail was marked great the trails were still pretty easy to follow. Only a few times did I lose the trail but easily picked it back up. My dog came with and he absolutely loves exploring! It was a pretty good hike for him too, nothing too difficult for him. He’s a small 25lb Pup that has no problem scaling large rocks. You could start to see some new life in the trees. I can’t wait to come back in a few weeks to see how much it’s grown in!

fantastic trail with beautiful views

Really great hike. Packed snow, trail broken in. Some icy spots, but did great with poles and crampons. Good training for New Hampshire!

Great hike. Don't let the fact that it's in eastern Mass fool you. The round trip hike is all up and down and is more strenuous than you think.

Always an enjoyable day on this trail.

a Must do

Very well marked trail. plenty of elevation gain to keep your legs busy and mind focused. a good shoe is a must as many parts of the trail have steep incline and declines on Rocky and jagged terrian.

Great for a nice easy relaxing hike. 10 min walk from Peekskill station

hiking
8 months ago

Beautiful hike! The trail starts just behind the headquarters buildings, and we parked across the street. We finished the whole loop in 2.5 hours, including some time spent at the weather observatory and taking pictures. Elliot Tower is closed for renovations currently, but the weather observatory gives you a view of the skyline for a $3 fee. We completed the loop counter clockwise, but I agree with previous reviews that clockwise is probably more enjoyable, as we had to go down a lot of rocks on the way back. Overall, great way to spend the morning!

Great short hike, brought my dog she loved it. Nice and tuckered out by the end! Would definitely do this tail again.

Beautiful views of southern Mass. It is not for a beginner or someone with knee or hip problems. You will be going up steep rocks. Wear good shoes. Little rocks jut out on the trail like crazy. It is a great trail and though I wouldn’t exactly call it easy. It also isn’t for a beginner. If you’re afraid of heights stay away from the cliff. It’s a strait drop down. You will only need a bottle of water and your music blasting with the woods all around you. Nothing special needed for this trail. You will love it. Kids can do it but they will need a lot of help.

Home base for Boston-area folks. Great place to practice for bigger hikes. No big vertical, but plenty of up and downs. Some hills can get your heart rate up a bit. Nice wooded sections make you forget how close you are to city until you catch some of the views of downtown Boston

Did a 16 mile loop. Id say its about accurate for moderate. loved it!

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