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

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.

This is a great simple day hike with beautiful views at the top of squaw peak. However in this case the AllTrails app does not depict the trails. There are three of them that are all looped together: Indian monument trail at 1.5 miles, squaw peak trail at 0.7 miles, And finally Hickey Trail at 0.8 miles. So do your homework on this one before you head out. Had a casual pace my partner and I walked from the Hickey Trail to squaw Peak Trail and finished off on Indian monument trail. Was about 3.2 mile loop.

Great hike with beautiful views!

We did the Indian Trail to Squaw Trail and Hickory trail. These is a cut off for the Squaw Trail from either Indian or Hickory. Trails are rugged at top. Nice views. Well marked with color dots on tree. Indian is blue, hickory yellow and squaw red. $5 to park for day. It is worth the parking fee.

Reached the top in about 35 minutes, nice quick workout.

hiking
3 months ago

The parking lot is large enough to fit four or five vehicles, which was a nice surprise. The trails are in need of some spring maintenance (lots of downed trees), but overall they are well-kept. There is one scenic viewpoint (which is beautiful), and a few water features -- otherwise, it's a hike through the woods with some short yet fairly steep climbs and descents. I was disappointed to see how many people let their dogs do their business on the trail without taking the time to clean up after them.

Great hike from the AT trailhead near Jug End up to Mt. Everett. steep climb at the beginning then leisurely hike along a ridge with views. Summit is a bit unremarkable, but nice views from the shelter just below. was snowing throughout our hike with no one else on the trail.

I live this trail. It’s a little bit of an investment of time, not your usual stroll in the park (pardon the pun). The pond adds a nice magic to it all.

Great for kids and dogs, not too much traffic. Had a 4, 6, 10 and 11 year old. Challenging but not too difficult for the little ones but interesting for the older kids.

on Benedict Pond Loop Trail

9 months ago

Beautiful views, very quiet and peaceful. Wonderful for young children to enjoy

Parked at the Jug End Road trail head and hiked to the Mt Everett Summit. Loved this trail! Fantastic trail variation kept us interested and the many open vistas offered natural points to stop and catch your breath. We hiked up to the summit of Mt Everett first and then caught the loop around Guilder Pond back to the AT. Headed north to get back to our car. Finished about 10 miles in just over five hours. Would absolutely do this hike again!

Lovely walking, although parts of the trail aren't kept up well, but the view from the "look out point" is excellent. About two miles near the end of the trail is on a road, which was a nice respite from the brush and bugs.

good hike for fitness. beautiful look out and had lunch at the pond. people were eating lunch and swimming. came across a rattle snake on the way back down....made excellent time back to the car following that!

Extremely good. Challenging. Guilder pond is heaven. I loved it. 12 of us hiked from Jug end to Mount Everett 7 and 11 year old girls did it all.

walking
Saturday, May 20, 2017

Nice spot but the trail is a little rough with rocks and tree roots in places.

backpacking
Tuesday, December 13, 2016

Certainly a demanding stretch, but well worth the effort. Such a beautiful hike with quite a few flat(ish) sections, but equally matched with steep and dramatic climbs.

hard, amazing view

Monday, November 07, 2016

easy, beautiful, comfortable

Thursday, September 29, 2016

Great morning for a short hike. Easy and beautiful.

Tuesday, September 27, 2016

Easy but long. Did it before work so I think I did half of the pond loop. Going this year to do before winter with my two true friends of mine and my husband. He used to do lots of hikes in boyscouts eagle scout. My husband Brian Durwin loves hikes like me.

following this app, you only get 1 really nice view (the Ledges on the A.T. section), after that, it's pretty much a typical trail. because this trail is made up of a mix of trails in the area, there are a lot of shared access (dirt bikes, atv's) power line "trails" that are not groomed well, and some roads. I enjoyed myself, but can't say that this particular route was inspiring. I would, however, use this route for trail run training, there are a good amount of ups and downs, but it's mostly level. few roots and rocks, but not too much to suffer!

Hiked from parking lot, around the lake and up to the Lookout Point. Lovely view of Western Berkshires all the way to the Catskills. FYI, trail was quite slippery with fallen leaves.

The AT through here is not well marked heading South after crossing the Bear Mountain Road. The blazes are faded and few. There isn't a phone signal until near the top of the mountain. Beautiful land and surroundings. Very, very wooded.

Awesome hike on the ridges and summits much more challenging than you would believe.

hiking
Sunday, October 12, 2014

If you're hiking this, not skiing/snowshoeing, it a VERY easy hike. The most difficult aspect is probably the loose rocks that the dirt bikes and quads kick up. Yes, dirt bikes and quads are allowed in the summertime, although the few we ran into were all going pretty slow. There is one lookout point where you have a nice view, the rest is just walking through the woods. We also did the turkey trail.. Which didn't have any views or challenging parts either.

This stretch of trail, from Jug End to the top of Bear Mountain, is not for amateurs.....but the views are amazing.

hiking
Tuesday, September 09, 2014

Beartown was great. We only took a short hike on the Lookout Trail. It was a cool vista at the end. I posted a video of my stay there the hike is included. We stayed at site 8.

hiking
Monday, October 28, 2013

This short trail could be described as an easy walk through the woods. There was minimal elevation gain, and exquisite foliage. Beartown has miles of trails that are much more difficult, but this is for everyone.

Only really got a chance to check out the Pond Loop Trail and a small part of the AT, but it was a great walk. I can't wait to come back and explore more.

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