ApproachVIA WAPACK TRAIL NORTHERN MOST TRAILHEAD: From Route 31 in Greenfield head roughly two and a half miles towards Wilton. Make a right on Russell Station road by the Yankee Farmer and head down that road roughly a mile. Mountain Road will be the second right. Continue roughly a mile and a half over the height of land and past the wildlife refuge signs and the trailhead will be on your left with parking on the right. Hike to the summit of North Monadnock and down the Wapack where you will pick up this trail on top of a small summit in the col between North Pack and Pack Monadnock where you will pick up this trailhead.
From the the top of the col between North Monadnock and Pack Monadnock the trailhead is left. Head down steeply on the Wapck trail 0.7 miles to the second Cliffs Trailhead on your left. Taking the trail the other way is a lot less enjoyable and in winter more dangerous due to the one very steep Class 2 section of the trail.
The trail quickly hits a rocky descending area. Then the trail ascends for a short while before descending another steep section to a brook. The trail crosses that brook and then take a Class 2 ascent to a the first cliff with great views to the south and east. Continue through the woods for views off of the two other cliffs also with great views. The trail then continues with alternating pitches up to the summit of North Pack Monadnock.