Best Hiking Trails Near Pittsfield Vermont

While there are a great deal of hiking trails in the Pittsfield VT area, there are a few stand out trails that offer something special at the the end of them. There is nothing worse than hiking a trail that just goes on and on and does not offer some kind kind of photo opportunity and the chance to get recover with some water and an Owl bar at a convenient stop

During the Spring, Summer and Fall months, the three best hikes in the Pittsfield, VT area are:

Stone Steps Hike at Riverside Farm, Pittsfield VT

Great trail on stone steps to the top of the mountain with wonderful peak views and a nice stop at the stone house built at the very top. During the hike there are various optional challenges straight out of the Spartan Race playbook, like rope swings, climbing walls and other challenges. On the hike just don’t miss the hidden trail at the Owl Bar sign, it is very easy to miss. This trail starts at the Riverside Farm in Pittsfield, VT and part of this hike has a winding stone staircase which was created in honor of the many people who have fought cancer.


Deer Leap Overlook at the Long Trail Inn, Killington VT

Deer Leap Overlook Trail is a 1.9 mile trail located near Killington, Vermont and features a steady climb on often rugged trail terrain. At the top of the Dear Leap Overlook, the rocky formation offers exceptional views of the surrounding area, with views of both Pico and Killington ski mountains. The views are perfect for photographs.


Canty Trail To The Water Cascades, Mendon VT

The Canty trail in Mendon is often a buggy, long climb to a disappointing peak on the Blue Ridge Mountain, but this trail has one redeeming factor that makes this long hike worthwhile. A great diversion, about 3/5 of the way up the mountain, is the stop off in the water cascades. This is where the mountain stream falls into a gorgeous cascade, which stays running in many of the dry Summer months, when most creeks and streams have already dried up. The trek to the very top of the Blue Ridge Mountain is not worth it, as the view from the top is not worth the extra hike unless it is Fall and the reduced foliage will allow for better viewing of Rutvegas and the surrounding countryside.

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