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Princeton, Massachusetts

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

Top Hiking Spots in and near Princeton

  • 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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  • Quincy, Massachusetts

    Hike The Skyline Trail at Blue Hills

    4.0
    12.7 mi / 2542 ft gain
    Park in the lot across from Batterymarch Rd off of Willard St. Access the Skyline trail from here, it is marked blue. Follow the signs. The trails in Blue Hills are perfect for training for backpacking because they are so steep and rocky. I would fill up a big pack and take the skyline trail up t...
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  • Chaplin, Connecticut

    Hike to Diana's Pool

    4.0
    1.3 mi / 45 ft gain
    The drive to Diana's Pool is worth it in an of itself, taking you through the backroads of Eastern Connecticut. To begin the hike just simply enter the woodland path and follow the trail. In order to go under the bridge just simply take the first left in the path and there will be a stream that f...
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  • Providence, Rhode Island

    Neutaconkanut Loop

    5.0
    1.49 mi / 171 ft gain
    To enter the park, you first have to go through a field and past a baseball park. Next, you will see a high slope, you can either enter the trails through here or the stairs at the side. Some of the trails are overgrown and may have ticks or poison ivy so be careful. This place is good for kids a...
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  • Mansfield, Connecticut

    Hike Nipmuck Trail

    5.0
    8.3 mi / 748 ft gain
    Nipmuck Trail is a 8.3 mile out and back hike that takes you past wildlife located near Mansfield Center, Connecticut.
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