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The 3.7 mile Bentley Loop is highly recommended. It has been maintained for the last 30 years by one of the founding board members of Friends of Myles Standish State Forest, Bob Bentley, together with help from his friends and the Appalachian Mountain Club. It passes some lovely ponds and meadows and offers more hills than the East Head trail.
The Bentley Loop trail surface is mostly smooth and flowing on solid hard-pack, with intermittent modest sand, roots, rocks and rough. The trail has moderate elevation changes, climbing from from south to north.
The trail is suitable for hikers of all abilities as well as confident novice mountain bikers and above.
The Bentley Loop starts from the State Forest's Hiking and Bike Trail parking lot off Upper College Pond Road. (Shown as parking lot P2). The trail was remarked in April 2012 with painted blue blazes and many wooden signposts (and left a few older plastic blue triangle blazes).
The Forest is popular with hunters and the area of the Bentley Loop is a Wildlife Management Area stocked by MassWildlife. Wear blaze orange during fall hunting season.

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