Explore To Do MA - view hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

To Do MA Map

This trail is beautiful but it is definitely challenging!

great place to get out and enjoy nature and great views

Lots of water on segments of the trail due to recent rainy weather.. Nice gradual 1200 ft incline, steeper sections towards the nice view at the summit. Wear waterproof hikers

Great hike. A lot of scrambling and very steep climbing in first leg. Whole thing took 2:20. Great views. Would not try if snow and ice on ground. First third is very well marked. Last two thirds are basically flat. Overall great hike.

A very good hike. Very wet and muddy but I found it more a moderate hike rather than hard

Nice hike. Tends to be wet (hiked in Early November) so I would recommend a decent hiking shoe. My running shoes came back wet and dirty. I tried running the on the easier grades but you have to be extremely careful due to the rocks and wet conditions. I would rate this moderate in difficulty.

Great ocean hike! Well worth it....

This is a great moderate hike. The first mile of the 5 is by far the most difficult where you gain most of the 1,000 feet of elevation for the 5.5 mile hike. It was a very foggy morning so the views weren’t great at first. However, I got the high point in Connecticut like I wanted and once we gained the ridge just to the west of the high point the valley below was bathed in sunlight and so that was a great sight. All-in-all it was a delightful hike.

Super nice hike. Well marked trails. Most people are really dog friendly.

Nice hike close to Boston. There's a surprising variation of terrain and the trails are pretty easy to follow. The summit is a bit disappointing, as its usually crowded and loud, and the views are just so-so. I'd say this is more of a moderate to easy hike. It's a great warm up mountain for hiking season.

Took the dog with us, and parked at the GPS location. The Gould Trail entrance is located across the street. Trail is great easy areas to starts that follows a stream. Some Rocky sections closer to the top but nothing terrible. We didn't check the forecast the day before and it was very foggy at the top and couldn't see at the summit so that was disappointing. on the way back we got a little turned around, so be careful to follow the markings.

Pretty hike with a nice view from the fire tower. Detour to Roaring Falls is well marked, plus a fun scramble on some impressive rock formations. The detour to the pond is worth it as well.

As mentioned, trailhead is not really marked but it is on Mt. Washington Rd. at the border with CT, you can't miss it if you stop there. If you're looking for a trailhead board, there is none. There is room to park several cars at the start and a couple more across from it or just down 50 feet is another area you can use. Rain storms within the last week made the start a bit tricky, as the trail is a run off from the mountain and was flowing a bit at times. Just off the side along it in points, it seems that others made an indentation in the brush so figured why not, walk through it. Saved my feet from getting too wet. Trail goes out a bit flat then a bit of a hill climb to Round Mt. summit. It's not that long a strenuous area but enough to give you a little workout and some nice views. Continuing, you can see Frissell just beyond so head down then up some more boulder climbing, once again, not all that long and not crazy strenuous. Got to the summit of Frissel and kept walking then stopped and thought, am I missing something? Headed back up and then went up the spur to the summit marking on the tree and the register that a private individual maintains a couple times a year. Downward to the highest point in CT. Found that register easily and the views were nice. Continued westward and found the Tri State marker. Did my best to be in all 3 states at once, lol. Continued and found the Ashley Hill Trail. Yes, this goes up to Alander but not towards the summit as I had been to Alander a couple months back. If you're looking to summit Alander from this area, go west a bit more, you'll see the South Taconic trail, go right and head north. You'll get closer to Alander Mt. summit this way. It's like a little over 3 miles I believe from this point. I decided to go to Brace Mountain which if you look at the two signs indicating where to go, one is correct at .4 miles, the other says it's like a mile more and not sure who created that sign but somebody should fix it. It's a short jaunt, easy summit and you might catch some hang gliders which I did. Headed back down and took a right following the AllTrails app map. Yes, it's a fairly straightforward downhill march but hindsight being 20/20, I should have gone back the way I came. It's not all that exciting and it's really rocky and slippery if wet like today was. Not that it's hard but it wears on your feet. You then get to the bottom where it's still wet and just an access trail or something and still a bit ways away from the road. Looks like I traveled way more than necessary and didn't really get anything more than miles and exercise (which isn't bad just boring). I probably could have tried going up Bear Mountain if I had just gone straight back. Even though going back you had to go up and down the summits again, they aren't really crazy in height. Live and learn

This is an awesome trail that will push you to your limits. There is multiple routes to explore that accommodate your level. Make sure to bring plenty of water.

I'd say the best of the trails we were on today (9/19/18) only one short section, maybe 1/4 mile, would I consider hard. the rest moderate. the clearing at the top had the best view by far.

Got to the parking area 0800. Started at the Gould entrance across the street. Trail was fairly easy going up and muddy. Stayed dry though and dog enjoyed it. No traffic on the trail going up. The summit was great had the whole place to ourselves. Went down North Appalachian to Thunderbolt via Bellows Pipe and ended up coming in to the back of the parking area. Little steep going down the ski trail and a small amount of people and dogs coming up. Overall a nice close hike.

Just did a day hike here. Rained the night before, so it was a bit muddy, but still not very difficult. The trail itself seems well maintained, and relatively quiet.
The scenery was nice the whole time, and the summit of Greylock is very enjoyable, with the monument, the lodge, and the great views. All in all a great day and a good hike. Would definitely recommend.

2 months ago

I love the Blue Hills. As a Boston resident, the Skyline trail at BH provides a nice challenging alternative to driving the distance to NH for more challenging hikes. I disagree that this is a moderate hike because the terrain is very rocky, one needs to be prepared to climb and descend jagged stairs at regular intervals on this trail. I would recommend bringing a Gatorade (or similar drink) because depending on where you end your hike, you are walking 9 to 11miles. I also recommend an early start (especially during the warmer months of the year).

I completed this hike by myself in 5 hours (from Quincy to Trailside Museum off 138) and in 6 hours when accompanied by a friend who is fit but is not a hiker.

3 months ago

Nice loop trail. First part (when doing the loop counter-clock wise) is a steep climb and scramble to the summit. After a nearly equally steep decline, the middle part of the hike then consists mostly of flat or slowly descending trails through the forest.
The very last part (again, when going counter-clock wise) - quite close to the trail head, but before the fork to the summit ascend - involves scrambling over a boulder field with lots of big, sharp-edged rocks ... a nice challenge, but I wouldn’t recommend that part for hiking with kids.

best views await you at top.love this trail due to friendly hardcore hikers and no litter.
Finding that the the steeper the trail, the more environmentally conscious hikers.
keep it beautiful!

great trail that connects to the green dot trail if you want an easier hike.

Great hike. Fairly well marked, though some of the trees with marks on them have fallen. The waterfall is not part of the loop, but is easy to find. The trails are well maintained but tend to be buggy and muddy so I reccomend wearing appropriate footwear.

IMO this is the best way to get to Brace Mountain and see a lot of cool stuff along the way. Nice views at Round Hill, with some steep areas going up, then down and back up to Frissell, where there is no real view at the peak, but plenty just after on your way to the CT high point, with Riga Lake below you. A bit further you come to the three states marker, then make your way gradually up to the South Taconic trail and Brace Mountain, with beautiful views of the Harlem Valley and beyond. It's a very popular spot for paragliders, and there were at least ten of them up there when we arrived, either in the air or getting ready to take off. The walk back down Brace Mountain Road is very rocky in places but super easy. We parked one car at the start of the hike and the other at the end of Brace Mountain Road, on West St., which is the best way to do it and keeps you from having to slog another boring mile up the road at the end. Great great hike!

Challenging yet not too much so. The day I went it was pretty muddy and it was slippery in quite a few places. Overall had a great time.

Challenging walk upon long 1/2 mile rock jetty from Ptown Inn and then in soft sand once on Long Point. Can get hot so bring water, sunscreen, hat, sunglasses. Beware of high tide as it can cover the jetty and strand you preventing your return trip!! Long Point is isolated, serene, tranquil, bird inhabited (careful as some birds are teritorial & will dive bomb you!!), & can be buggy. In gereral a challenging hike over water (jetty) and over soft sand

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.

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.

At the beginning of the summer (2018) when I decided to start hiking again, I kept seeing this trail when searching out what hike to do in the area. It was listed as "hard" by AllTrails so I didn't think I should try it right away. After doing the AT up to the top of Greylock last weekend, I figured now was as good a time as any. In reality, this shouldn't be listed as hard. It's a moderate ascent up to the top. The trail is fairly wide most of the way though it does have a lot of rocks you must traverse. Started at the Mt. Washington State Forest entrance and it took me about 1.5 hours to reach the top and that was with stops to enjoy the scenery, take pictures and so forth. Didn't see a soul my entire time out but not sure if that was due to the trail or the weather or both. I got to the top but though the weatherman said the area was supposed to be partly cloudy, it was more than that. The view at the top was disappointing as I have read it has wonderful 360 views. I was also a bit surprised how small the top was really. Don't expect a Mt. Greylock wide open and fairly spacious area. I saw four support bases there and think there must have been a fire tower at one time. The trail is really easy to follow and marked well. It appears it's really just a path that the rain runoff uses than a trail that was blazed and marked for everyone. When you get to just about the top, there is a small cabin. At this point, if you pass the cabin, you can go left or right. Right goes up a little steep incline and that leads to the summit. I'm thinking that if you went the other way, it just continues on to the South Taconic trail.
At the summit, there is another branch off and was not really sure what that was but looking once I got home to do this, it looks like it goes up to Bash Bish Falls a few miles north. For 99% of the way, the trail was marked fine as I mentioned but at the cabin, trail markings are lacking. Got to the top, took pictures and then the rain came. I went back down to the cabin and waited about 15 minutes then descended to the parking lot. I got a little wet but this area is mostly deep woods so the rain wasn't so bad. Don't expect lookout side views on this trail but there are a few nice brooks and waterfalls to enjoy. If it was warmer, there is an area that looks like you could wade in to cool off. A nice hike but could have been better if I waited about 3 hours to start it as once I got back to my car, the clouds started parting and the sun came out, who knew, oh well.

The route on the map leaves from and returns to the Mt. Washington HQ but if you have two cars (as we did), the best way is to park one at the Alander Brook trailhead in New York, then drive your other car up to Mt. Washington and leave from there. A somewhat easier trek up to Alander than leaving from the NY side and you can just keep going downhill after you hit the Alander summit and enjoy the other views on the way down. Amazing views from the top of Alander!

4 months ago

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'.

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