Explore the most popular views 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.

hiking
1 month ago

Though road is marked with street signs but not on google maps, as mentioned north road to old north road takes you to trail head. Used directions here and google maps took me to it. Last couple miles is dirt road but easily passable. Trail is really not near much of anything but a few homes down the road, it doesn't get much traffic. Take the parking lot entrance or just walk up the road from the parking lot a little and on the left you'll see clearly marked entrance to the trail also. Depends on how much walking you want to do. Eventually, you see a sign that says summit and if coming from the parking area, you go left. If you go right, it takes you to the trail entrance I mentioned above. Another 15 minutes and you'll be at the summit. As mentioned, easy walking for the most part till you hit the last few minutes where you get a little bit steep. It is somewhat rocky going up in spots but nothing major. Just be careful where you're stepping and you'll be fine. Summit has some nice views. You could spend a little time on the rock ledge and eat lunch if you'd like, nice little area. Rate this as easy even with those few minutes of uphill to the summit.

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.

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.

hiking
9 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.

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!

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

hiking
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.

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.

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.

hiking
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.

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