Explore the most popular 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.



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Great Barrington, Massachusetts Map

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

4 months ago

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

4 months ago

This is a nice trail through the forest, especially during foliage season. The first 2/3 are very easy flat walking, the last third up to the summit is a bit steep and very rocky. The views are nice from the top but somewhat hindered by the trees below that have grown quite tall.
The trail is well marked, but the trail head is hard to find: in New Marlborough take North Road on the right of the church until you turn left onto Old North Road and find the parking lot and trail head 100 yards down the road.

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.

9 months ago

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

on Dry Hill

Monday, January 30, 2017

I would consider this an easy trail. The majority of the trail is pretty flat.The summit is steep but short. When I hike this summit it was very icy and could barely stand on 2 feet, but the view is worth the short hike!

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.

Tuesday, June 07, 2016

Pretty easy trail but a bit steep at the very end. Trailhead is off of old north road in New Marlborough - if you take that, the first time it splits keep to the left and the trailhead will be on you left.

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.

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.

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.

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.

Hiked the Bridle, MTN, Bike Trail (9.2 miles) starting & ending at Lake Benedict. LOVED IT!!!!!!! The last 1.5 miles are overgrown and need new trail markings, a bit easy to briefly get lost.

Tuesday, January 17, 2012

Great rock climbing formations to practice on. Would like to hike again in the spring.

Good walk around Benedict Pond, with enjoyable spots to sit and view birds and nature.

4 months ago

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