Plan with
Confidence
Path Type
Loop
The route begins from the trailhead off North Hillwinds Road in Brattleboro and quickly enters a mixed hardwood forest. A short walk brings you to the Beaver Pond Trail, where hikers can watch for beaver activity and waterfowl along the quiet shoreline. From here, the path continues into the Upper Loop, which climbs gradually through the woods before reaching higher points with occasional glimpses over the surrounding valley.
Both trails can be combined for a longer outing or hiked separately depending on time and ability. The terrain is mostly gentle, though roots and rocks may be slick after rain. The forested setting makes this a pleasant year-round option for hiking or snowshoeing, with shade in summer and open views once the leaves drop. The combination of pond scenery, wildlife, and forest walking makes this an inviting trail system close to Brattleboro.
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