Explore the best trails near Bennington 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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Bennington, Vermont Map
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Tough towards the top, but well worth it!

Well marked trail with a steep incline in the beginning, strenous but not too hard. Great views and dog approved! Good trail for a dog used to trails and has some listening skills and is conditioned a little.

walking
11 days ago

Great loop around the reservoir. Wet in some spots but maintained very well. Very tranquil. Loop took 75 minutes in total.

I hiked here as part of a 65 mile section of the Long Trail I was doing. The hike is was fairly difficult with a lot of ups and downs. The top of Glastenbury has an old fire tower with amazing views in all directions. The shelter is a little ways downhill from the summit. I would recommend returning to the fire tower to watch the sunset after you set up camp.

hiking
14 days ago

This trail was pretty intense at the beginning. Lots of rocks and pretty steap but totally doable, just breathe and make it to the top! Once at the top it does clear out to a pretty clear with some areas of tall grass. The veiw of Bennington at the top was beautiful ♡

hiking
25 days ago

Great hike and challenging at times. All the information in previous posts is useful and great, so please check it out before going out on this one. The view of Bennington is beautiful.

hiking
28 days ago

Visited this summit yesterday. As indicated in the previous post, the start of the trail is under construction, due to spring washout, so the first quarter mile is a bit rough. It was a fantastic hike after that though! It IS quite wet in some areas still, so good boots are suggested. As others have noted, there is not much to see at the summit, but there is a great view overlooking Bennington about a mile and quarter before the summit. The rock slides were fun to climb, and the short jaunt I followed along the Western Ridge trail was neat to see. Overall, a very enjoyable, and challenging day out! I would certainly do it again.

very easy trail. $4 for each person to hike.

hiking
1 month ago

hiking
1 month ago

Nice, peaceful trail with the reward of chilling by the reservoir at the end. The trail is pretty flat - the main challenge is fording all the little streams. It can be muddy in spots.

walking
1 month ago

Well maintained trail, perfect for walking with kids and dogs. Picnic areas abound, perfect for a snack before or after your walk. Kona gives this 4 out of 4 paws.

Lots of rocks and quite steep at first and then gives way to a lovely fern forest before the summit where you can see Bennington down below. A challenging work out but worth it! Took us about 2 1/2 hours. Highly recommend!

hiking
2 months ago

A little hard to find the trailhead at first, as they are currently constructing new stairs at the beginning. We missed the scenic vista on the way up (and there is not much of an overlook at the top) but found the views on the way down. A little more than 3.5 hours and that includes stopping for lunch at the top

backpacking
2 months ago