Thompson Hill, Hillsborough NH

• 3-star hike
• 2.1 mile loop
• Easy difficulty | Gain 745 feet
• Hillsborough, NH | Monadnock Region
• Driving directions: Trailhead

This pleasant hike local to the town of Hillsborough will likely fill you with solitude on this two-mile loop through oak forest, past stone walls, wildflowers, and apple trees left from early farms.

We rate this trail as easy, but with the caveat that you'll be gradually hiking over seven hundred feet to the summit of Thompson Hill. At the summit we found some great peek-a-book views towards Mount Monadnock when we visited in late summer, though at other times of year the views can be even better.

Beginning in forest and after a couple of unexpected turns, the trail heads up the forgiving South-facing slope of Thompson hill, over a stream and past what appears to be the source of a spring - though I wouldn't recommend drinking from it. Patches of sky become more frequent as you ascend, and after small fields of fern and a couple of false summits, you'll arrive at the top - marked solely by your sense of achievement.

Thompson Hill Loop Expand Map

Thompson Hill Loop 3★
2.1 mi loop, Easy, Gain 745ft
Trailspotting Map at AllTrails

We prefer the clockwise route to tackle the hill, followed by a looping trail back downward, past a towering rock cairn and tracing a stone wall for a time. The descending trail is slightly longer but less steep.

You'll find the trailhead 2.5 miles along the unpaved Country Road, marked by a couple of signs. There is room for only a couple of vehicles here, but with this lightly used trail it shouldn't be a problem. Note that the trail is two miles, and not 1.5 miles as stated on the Forest Society's map.

• Trail Links: Official, Public Map at AllTrails
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New Hampshire Forest Society
Trails in this article are maintained by the Society For The Protection of New Hampshire Forests. See the Forest Society website to find out how you can help.
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