The Wapack Trail
One of the best trails in southern New Hampshire/northern Massachusetts. It is somewhere around 23 miles in total distance and can be quite challenging at times. My friend and I hiked this entire trail in one day, it took us just shy of 10 hours and we were moving at a pretty good pace.
The north end of the Wapack trail is on Mountain Road in Greenfield New Hampshire at the edge of the Wapack National Wildlife Refuge. The south end is on Route 119 in Ashburnham Massachusetts in the parking area for Mount Watatic. It goes over North Pack Monadnock, Pack Monadnock, Temple Mountain, Barrett Mountain, New Ipswich Mountain, Stony Top, Pratt Mountain and Mount Watatic. All of these peaks are small mountains, but with so many ups and downs you get some amazing views and quite the leg workout. (Total Elevation for our hike was about 5,500 ft)
A small section of the trail is on Temple Road which is a paved road and just south of that there is another section on a gravel road. Besides these two sections the trail is all through the woods and on the mountain ridges. There are also a few different spots where you can park and tackle the trail in smaller sections. Both the northern and southern terminus have parking areas and there are parking areas on 101 at Miller State Park (this is a fee area) and on the other side of 101 at Temple Mountain Reservation. In the middle of the trail you can park at the Sharon Ledges Trailhead on Temple Road in Sharon NH or at the Wapack Trail Parking on Turnpike Road in New Ipswich NH.