Explore the most popular hiking 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.

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

A good, flat, easy walk. 45 mins to complete the circuit around the gorgeous pond. In summer you’ll need to pay to park.

Nice hike! I only did about half of this trek (4 miles total), had two nice views with large rocks to sit on. Took my dog and she liked it as well, there were a few cold streams for her to lay in. Only saw one other couple with a dog, surprised because it was such a nice day. Lots of rocks and ruts so need to be aware of your footing, but I didn't find this hike too difficult. I know it is classified as hard but I think that is a stretch.

Excellent trail, beautiful overlooking the country

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.

3 months 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.

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.

5 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

11 months ago

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

11 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.

Tuesday, September 05, 2017

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.

Saturday, May 20, 2017

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.

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