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Holyoke, Massachusetts

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

Top Hiking Spots in and near Holyoke

  • Sutton, Massachusetts

    Hike the Purgatory Chasm Trail

    4.7
    1 mi / 115 ft gain
    For this 1-mile hike, you can park at the Purgatory Chasm Visitor Center. From there hit the trail and explore the unusual gap between the tall granite walls, which might be adorned with climbers. Great for all ages and dogs are welcome too. The trail is open March-November.
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  • Meriden, Connecticut

    Hike the Metacomet, Blue, and Yellow Loop

    5.0
    4.5 mi / 976 ft gain
    Start from the Castle Craig road entrance. Walk until you're greeted by a beautiful reservoir. You'll notice the strange but beautiful Mine Island in the middle of all this. You'll also notice markers for White Trails and Yellow Trails. The White Trail is an easier/wider trail. The Yellow Trail C...
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  • Sharon, Connecticut

    Hike the Pine Knob Loop, Housatonic Meadows SP

    5.0
    2.5 mi / 770 ft gain
    The Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick  woods filled with vistas, wild flowers and tons of wild life.  You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...
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  • Plainfield, Connecticut

    Hike Sugar Brook Loop Trail

    4.0
    3.3 mi / 200 ft gain
    Sugar Brook Loop Trail is a 3.3 mile loop hike that takes you by a river located near Plainfield, Connecticut.
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  • Washington, Connecticut

    Hike the Mount Tom Tower Trail

    1.3 mi / 337 ft gain
    Starting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...
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  • Ashburnham, Massachusetts

    Summit Mount Watatic via the Wapack Trail

    5.0
    3 mi / 800 ft gain
    Entering Mount Watatic in your GPS will take you to Rindge State Road (119), continue about two minutes down the road past where the GPS tells you. on the Right hand side you will will see a sign for Mount Watatic Parking area or just enter in coordinates: 42.696796, -71.904521 You will begin the...
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