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

Massachusetts  Map

Great views in all directions, not too hard, fun to climb over rocks near the top.

Very satisfying hike, though a bit crowded. Beautiful views at top.

Easy side of moderate with lots of roots, mud, flat rocks.

Great hike with Richard, Macy and Gronk!

Excellent trail, very people and dog friendly. Hike it early as it gets quite busy after 11, especially on weekends. A very moderate hike that can be made in under two hours. Take the few extra minute to go to East side of peak to get a nicer view to the east. Mt. Wachusetts is prominent to the South, but you have to find just the right spot to see Monadnock to the West. Lots of hawks during migrating seasons.

It’s a great place to go hiking, biking dog walking or running!

Fall trails conditions as in any NE area. Mixed wet day yesterday in area, planned a weather break day amidst the Berkshires & had one. As a first time, chose the Blue Indian Monument Inscription Trail. An old wagon trail ending proximate to the Red Summit Squaw Trail. An easy south shoulder to summit climb, gradual ascent. The Red & Yellow Hickey Trails meet at the Monument. The red then used scrape & ledge & rocks (some as steps) to Squaw Mountain, clearly blazed. Children & newbies should be watched - the cliffs are real, a 900 foot drop. My altimeter read 1615-1640 height. A couple of “Pulpit” rock formations adjoin the cliff face here, one the Devil’s Pulpit. The trustees allow no rock climbing here. Descent can be had by the Squaw Trail Red .5 mile which intersects the 1.6 mile Blue Monument trail up or down. The .8 mile Hickey Yellow Trail is correctly styled strenuous. In fall, leaves conceal rocks & pits. Yellow blazes are adequate. Taken downhill the trail is 2/3 sharp incline & rocky. Very attentive. Two bridges & views of the lower cliff rockfalls & some flatter slopes appeal. All (the Red via the blue north or south, the Yellow at the Monument) commence & end at the picnic & parking area. If time, a ride back via State 183 to the West show a rich valley romantic view of the massif along the Housatonic River. The northern water from Squaw Mountain is Agawam Brook Pond. The trail condition is good. Weather turns a risk at the summit. Pay to park or donation encouraged with solar powered ATM/Debit/Credit machines.

Nice woodland scenery,especially in the beginning along the stream. However, followed this hike path to “summit” .... no real views. All trees !! No signage or trail markers !! Some parts, no real trail, either !! Worked my way through the woods around this “summit” until I came across another “trail” that went by a bulldozed area with lots of pink surveyor tapes on the trees .... which appeared to follow along the Monument Mountain Reservation border. Had an “adventurous” hike. (Be sure to have your GPS)

Took the clockwise loop up Midstate to Wapack... less steep. Couldn’t see a view from Nuttings Hill but the views from Watatic were very good. I was the only person on the peak when I arrived, 9:30 on a Wednesday, but the parking lot was filling up as I was leaving. Definitely one of the better views in Ma. Trails can be very confusing without a GPS. A few more signs at the various junctions would be helpful.

Great for beginners

Very fun hike; great views from the top

This hike was nice, but very easy compared to what I had read here. This would be a fantastic trail run, but I was looking for a slightly more rigorous hike for walking than what I got. My friend and I hiked the more challenging leg of the trail up, crossed over the summit using Squaw Trail, then took the easier Indian Trail down (it’s better on your knees to go downhill more gradually). The paths were all incredibly clean and well kept. There were a few 4 year old kids playing at Summit when we got up there, which says something about how easy the hike is. Views are great, but if youre looking for more of a “real hike” where youre following blazes and needing to watch your footing, choose a different hike.

My 8 year old daughter and I really love this trail, we did it for the first time back in April and didn’t make it to the top of the red trail but enjoyed our hike. Just went this past weekend (October) and made it up the red trail and down the yellow. Beautiful and only slightly challenging. View was amazing

Did the Wapack trail on Saturday. Nice steep climb and beautiful views!

Always a great hike, in any season except in deep snow. Fab views from the top. Approx 1.5 hours to complete the loop. Dog friendly. Can be crowded on the weekends. Devil’s Pulpit is a short diversion near the top which affords less crowded views.

Excellent trail, beautiful overlooking the country

great hike with breathtaking views, I would definetely recommend squaw trail( red one) Not for kids under 10

One of the best easy hikes around. Used to always do an out and back trail up Watatic, but I tried this a few weeks ago and again yesterday, and it was great! My hiking partners liked this loop better both times.

3 months ago

Trail fairly well marked. Mid point has some steep parts so pace yourself or you'll be panting as it can get strenuous in parts. . Weekends are crowded but no problem, you can park on the side of road if you have too. Views are excellent. Saw plenty of hawks migrating south at summit

3 months ago

Was looking for something in this area to do a easy or moderate loop. Found this and didn't realize I had actually gone past it when doing another hike out at Alander Mtn. a while back. This is a busy area, a hike that is more for somebody looking for something to do on a weekend than say a hiker looking to do a section of the AT. Don't get me wrong, it's nice but don't look for solitude. After seeing many people starting their loop by going right, I went left to start and did clockwise. Only saw a few people till I got towards the top. Still, some people are just loud and can't just enjoy the mountain. Glad I found some areas to explore before reaching the congested top area. There is a section just off the Squaw trail that is called Devil's Pulpit. It's just a little side trail so take it if you can. It brings you to the cliff area, straight down if you slip but no worries. :) All in all, a decent hike but nothing too exciting till you get to the Squaw trail. There is the Indian loop trail which goes alongside the mountain under the Squaw, probably worth checking out but wasn't that interested to back track and find out. Last thing to note as I didn't notice when I pulled into the parking lot but I guess you need or will have to pay to park. I walked by a kiosk getting back to my car. I checked it out, doesn't look like it had been activated yet but just letting you know for future reference. When I parked and started up the trail, I didn't go by this and there isn't a sign anywhere that mentions paying at least not yet.

Wide variety of paths and difficulty for both hiking, trail running and mountain biking. It can be easy to get lost, so be prepared with a trail map if you veer off main loop.

Good cardio workout for sure

3 months ago

Beautiful and varied terrain. Only got a chance to wander for a bit, but this is definitely a place I want to return to and explore some more.

Lovely hike!

3 months ago

grab a map at the entrance or download off the web for Lynn woods. trails are all marked with grid numbers and letters. A lot to explore if you use the grid. watch out for special surprises on the trails from ignorant dog owners, as will as some coyotes. Deer do come out on the day, keep your eyes open.

I'm biased since this has been in my back yard since I was born.

Love this trail!! I did about 4 or 5 sunrise hikes here in July and I have nothing but good things to say about the trail and the view at the top!
There is a couple very very rocky sections but the majority is a nice dirt trail

4 months ago

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

Load More