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The Best Hiking in Holliston

Looking for the best hiking in Holliston? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Holliston. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top hiking spots in and near Holliston

  • Holliston, Massachusetts

    Wenakeening Woods and Idylbrook Loop

    4.11 mi / 381 ft gain
    Wenakeening Woods and Idylbrook Loop is a loop trail that takes you by a lake located near Holliston, Massachusetts.
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  • Holliston, Massachusetts

    Wenakeening Woods Loop

    1.62 mi / 177 ft gain
    Wenakeening Woods Loop is a loop trail that takes you by a river located near Holliston, Massachusetts.
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  • Holliston, Massachusetts

    New, Top Down and Long Run Trail Loop

    4.79 mi / 397 ft gain
    New, Top Down and Long Run Trail Loop is a loop trail that provides a good opportunity to view wildlife located near Holliston, Massachusetts.
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  • Holliston, Massachusetts

    New, Holliston, Bypass, Main, Three Sisters and Deer Trail

    6.9 mi / 607 ft gain
    New, Holliston, Bypass, Main, Three Sisters and Deer Trail is a loop trail that provides a good opportunity to view wildlife located near Holliston, Massachusetts.
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  • Sherborn, Massachusetts

    Sherborn Red Trail

    4.1 mi / 374 ft gain
    Sherborn Red Trail is a loop trail that takes you by a river located near Sherborn, Massachusetts.
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  • Holliston, Massachusetts

    New Trail and Holliston Highway Loop

    1.43 mi / 89 ft gain
    New Trail and Holliston Highway Loop is a loop trail that takes you through a nice forest located near Holliston, Massachusetts.
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  • Ashland, Massachusetts

    Hike the Ashland Reservoir Trail

    5.0
    3.2 mi / 68 ft gain
    Park in the lot on State Park Road (see map) to access the trail. It's a popular trail that is dog-friendly. Pay attention to the trail as at parts it is not well marked. 
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  • Holliston, Massachusetts

    Swamp Bypass, Kitchen, Rock Garden, Teetering Rock Trail

    2.33 mi / 197 ft gain
    Swamp Bypass, Kitchen, Rock Garden, Teetering Rock Trail is a loop trail where you may see beautiful wildflowers located near Holliston, Massachusetts.
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  • Hopkinton, Massachusetts

    College Rock Run

    1.95 mi / 151 ft gain
    College Rock Run is an out-and-back trail where you may see beautiful wildflowers located near Hopkinton, Massachusetts.
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  • Sherborn, Massachusetts

    Rocky Narrows Overlook Loop

    2.64 mi / 269 ft gain
    Rocky Narrows Overlook Loop is a loop trail that takes you by a river located near Sherborn, Massachusetts.
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  • Milford, Massachusetts

    Upper Charles Rail Trail

    13.46 mi / 289 ft gain
    Upper Charles Rail Trail is a point-to-point trail that takes you by a river located near Milford, Massachusetts.
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  • Sherborn, Massachusetts

    Pine Hill Loop

    4.01 mi / 246 ft gain
    Pine Hill Loop is a loop trail that takes you by the lake located near Sherborn, Massachusetts.
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  • Sherborn, Massachusetts

    Mount Misery Trail

    3.82 mi / 233 ft gain
    Mount Misery Trail is a loop trail that takes you by the lake located near Sherborn, Massachusetts.
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  • Medfield, Massachusetts

    Charles River Reservation Loop

    2.51 mi / 164 ft gain
    Charles River Reservation Loop is a loop trail that takes you by a river located near Medfield, Massachusetts.
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  • Medfield, Massachusetts

    Medfield Charles River State Reservation

    3.8 mi / 315 ft gain
    Medfield Charles River State Reservation is a loop trail that takes you by a river located near Medfield, Massachusetts.
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  • Ashland, Massachusetts

    Wildcat Hill via Red Diamond to Bay Circuit Loop

    3.2 mi / 200 ft gain
    Wildcat Hill via Red Diamond to Bay Circuit Loop is a loop trail that takes you through a nice forest located near Ashland, Massachusetts.
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