Appalachian Trail: Dalton to Cheshire is a 7.4 mile point-to-point trail located near Cheshire, MA. The trail is good for all skill levels and primarily used for hiking.
Please disregard the overview as it is completely incorrect. Due to where you have to park in Chesire the length is closer to 8.3 miles, the elevation gain is about 1250' and it is NOT suitable for all skill levels, in fact it is listed as difficult or moderate to strenuous in all guides. I personally rate it in the moderate or intermediate level.
Other than that it is a beautiful hike with 2 major attractions being, The Cobbles, which offers a wonderful view of the Mount Greylock range and the Hoosac Valley, and then Gore Pond, a fantastic wetlands area that if you meander around for a while you're sure to find frogs, salamanders, snakes, turtles and an assortment of other water loving creatures.
Have traveled this section of the AT twice. The first time went through quickly just over 4 hours and the second time took some time to observe and admire more of what the trail had to offer and took a meandering 6 hours.