The Best Trails in Winchester Highlands, Massachusetts (United States)

7 trails

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  • Skyline loop trail at Middlesex Fells Reservation

    Hiking
    Save to a List
    Author
    MTols
    Distance
    7.67mi
    Elevation +
    1129f
    TrailRank
    55| Rating 4.67
    Photo ofSkyline loop trail at Middlesex Fells Reservation Photo ofSkyline loop trail at Middlesex Fells Reservation Photo ofSkyline loop trail at Middlesex Fells Reservation

    Loop trail with white trail markings. Plenty of street parking on weekends at the beginning/ending spot that I chose, but limited to 1 hour parking M-F 9:30am-5:30pm. You can also start and finish the loop from the main ...

    Well marked trail, with a variety of terrain. I would recommend to anyone that wants a 7+ mile hike in the woods
    mikescire

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