I hesitate to post about this site since I know a lot of people regard it as a well-kept secret favorite spot, but... I mean it's basically a super-sweet little hike right in our backyard (or at least on the first ridge above us as you head north up out of town) and it's on all the trail apps and there's only so long I can not talk about it before it just feels weird.
The lower trailhead is near the end of a dirt road at the Greenfield/Leyden town line, right about where the terrain changes dramatically from the lower rolling open areas of the Valley to the steeper slopes of the hilltown uplands. The route described here rises up for several miles to some open hilltops and a small trailhead off of E Glen Rd up in Leyden. There's no officially marked, mapped, or named trail, and there are several forks along the way so you definitely want to have a trails app handy if you go (but beware lack of cell signal there). Jen and I hiked it as an out-and-back at the start of this Labor Day weekend.
The first part of the route rises through open meadows, managed as wildlife clearings by MassWildlife. After climbing a steep pitch back up into the woods at the upper end of the clearing, we turned right at the first major intersection (left leads about a mile across the slope to the reservoir ponds along Glen Brook). We climbed through woods for about a mile to the next clearing. There appear to be 5 total along this route, though you really only pass through 4 of them (the fifth being this one, which you sort of skirt the edge of).
The middle clearing is the sweetest. Hardly anyone goes there but there are wide, sweeping views to the south and you can see so much of the Pioneer Valley. Of the two branches of trail you can choose from here, I'd pick the southern one (the northern one is more direct but passes through some briars on the slopes and a wet area at the bottom).
After rolling through more woods between clearings 3 and 4, we rose through blackberry and raspberry bushes along the edge of clearing 4 and were delighted to see tons of monarch butterflies flitting about among the goldenrod flowers. Between clearings 4 and 5 the route passes below some houses and along a wet area, and to be honest I don't like that part very much. There are blowdowns to scramble around and it's quite soggy. It smells a bit, too.
Clearing 5 is the main high point of this section of ridge, known for its copious blueberries patches in season. It's only a quarter-mile walk up an old road from the upper parking area.
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