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The Best Hiking in Randolph

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

Top hiking spots in and near Randolph

  • Braintree, Massachusetts

    Cranberry Pond Via Red Trail Loop

    2.06 mi / 164 ft gain
    Cranberry Pond Via Red Trail Loop is a loop trail that takes you by the lake located near Holbrook, Massachusetts.
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  • Abington, Massachusetts

    Ames Nowell State Park Trails

    3.52 mi / 190 ft gain
    Ames Nowell State Park Trails is a loop trail that takes you by the lake located near Abington, Massachusetts.
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  • Randolph, Massachusetts

    Hike the Ponkapoag Pond Trail

    4.0
    3.82 mi / 173 ft gain
    Park at the end of Ponkapoag Trail Road to access the trail. Dog friendly, open year round. 
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  • Milton, Massachusetts

    Skyline Loop Trail to Hawk's Hill

    3.54 mi / 640 ft gain
    Skyline Loop Trail to Hawk's Hill is a loop trail that provides a good opportunity to view wildlife located near Quincy, Massachusetts.
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  • Milton, Massachusetts

    Ponkapoag North Loop

    1.89 mi / 220 ft gain
    Ponkapoag North Loop is a 2mile loop trail that takes you by the lake located near Randolph, Massachusetts.
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  • Milton, Massachusetts

    Blue Hills Nahanton Hill Loop

    4.82 mi / 584 ft gain
    Blue Hills Nahanton Hill Loop is a loop trail where you may see beautiful wildflowers located near Milton, Massachusetts.
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  • Milton, Massachusetts

    Skyline Trail to Buck Hill

    1.2 mi / 348 ft gain
    Skyline Trail to Buck Hill is a loop trail that takes you past scenic surroundings located near Quincy, Massachusetts.
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  • Milton, Massachusetts

    Houghton's Pond to Buck Hill

    3.68 mi / 400 ft gain
    Houghton's Pond to Buck Hill is a loop trail that takes you past scenic surroundings located near Milton, Massachusetts.
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  • Braintree, Massachusetts

    Pond Meadow Red Trail Loop

    1.72 mi / 92 ft gain
    Pond Meadow Red Trail Loop is a loop trail that takes you through a nice forest located near Braintree, Massachusetts.
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  • Milton, Massachusetts

    Houghton's Pond Recreation Area

    1.2 mi / 79 ft gain
    Houghton's Pond Recreation Area is a loop trail that takes you by the lake located near Milton, Massachusetts.
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  • Milton, Massachusetts

    White Triangle Trail

    6.07 mi / 653 ft gain
    White Triangle Trail is a loop trail that takes you past scenic surroundings located near Milton, Massachusetts.
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  • Milton, Massachusetts

    Buck Hill

    2.85 mi / 413 ft gain
    Buck Hill is an out-and-back trail that takes you by a lake located near Milton, Massachusetts.
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  • Milton, Massachusetts

    Buck Hill and Doe Hollow Path

    1.67 mi / 200 ft gain
    Buck Hill and Doe Hollow Path is a loop trail that takes you through a nice forest located near Quincy, Massachusetts.
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  • Milton, Massachusetts

    Hike the Great Blue Hill Trail

    5.0
    2.3 mi / 550 ft gain
    This is family-friendly hike takes you to nice views of Boston, after a moderately challenging stretch of elevation gain. Follow the blue markers along Great Blue Hill Trail to reach the observation tower. This is also a great spot for bird watching, and for exploring the nearby weather station.
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  • Milton, Massachusetts

    Buck Hill to Hawk Hill Loop

    3.29 mi / 495 ft gain
    Buck Hill to Hawk Hill Loop is a loop trail that takes you through a nice forest located near Milton, Massachusetts.
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  • Milton, Massachusetts

    Buck Hill Path Loop

    1.28 mi / 115 ft gain
    Buck Hill Path Loop is a loop trail that provides a good opportunity to view wildlife located near Milton, Massachusetts.
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