Hollis, New Hampshire

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

Top Hiking Spots in and near Hollis

  • Jaffrey, New Hampshire

    Hike MT Monadnock via White Arrow Trail

    4.3 mi / 1485 ft gain
    Arriving at the Old Toll Road/Halfway House Trail head you will have $5 entrance fee. Starting on the Old Toll road you'll find yourself walking on a gradual incline into the beautiful New Hampshire wilderness. Everything you see and smell is fresh and vibrant. Following the road for 1.1 miles yo...
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  • Jaffrey, New Hampshire

    Summit Mt. Monadnock via Marlboro Trail

    5.0
    4 mi / 2300 ft gain
    Start at the Marlboro Trailhead (you can enter this in Google maps) off Shaker Road. There's parking and porta-potty bathrooms. The trail is well-marked with white dashes/M marks all the way up. Once on trail, the initial 800 ft climb is through forested terrain with a few brooks and streams alon...
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  • Medford, Massachusetts

    Hike Southern Middlesex Fells Loop

    4.7
    3.5 mi / 756 ft gain
    Park in the parking area near Bellevue Pond. There are multiple entrances to the reservation (some closer to the reservoir itself than others). I have spent days in there hiking around and never seeing the water and there are days when I just hiked right in to the water and sat and enjoyed it. Th...
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  • Wellesley, Massachusetts

    Walk along Lake Waban

    3 mi
    Note: The campus is currently closed due to COVID-19 restrictions. This is a lake on Wellesley College Campus.  It is easy to get to from just about any direction. Just park and walk toward the lake, and there are paths that will take you there. The easiest place to park (pinned on the map) is ju...
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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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  • Concord, New Hampshire

    Hike to the Oak Hill Fire Tower

    4.0
    3 mi / 500 ft gain
    Climbing to the Fire Tower on Oak Hill is a great urban adventure, short enough for a lunch break trail run or a morning hike with the family. The trail is primarily wooded, with a panoramic view from the Fire Tower for those brave enough to ascend it's wooden steps.Park at the well signed dirt l...
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  • Boston, Massachusetts

    Freedom Trail

    4.7
    2.9 mi / 121 ft gain
    Park along the trail and then hop on. The Freedom Trail allows you to not only see the most beautiful parts of Boston (which is an absolutely gorgeous city) but you can learn some history too! Head off the trail a bit to explore the Charles River, the waterfront near the aquarium and picturesque ...
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  • Boston, Massachusetts

    Run the Arnold Arboretum Trail

    5.0
    2.6 mi / 150 ft gain
    Park in the lot off of Arborway to access the trail. This place is gorgeous year round. The winter offers a quiet solitude, fall boasts bright colors, spring is the most beautiful as the flowers start to burst and cherry blossoms take over, and summer is overwhelmingly green. There are dozens of ...
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  • Newbury, Massachusetts

    Explore the Parker River National Wildlife Refuge

    4.6
    6.5 mi
    Located just north of Boston, Parker River National Wildlife Refuge was established in 1941 to provide feeding, resting, and nesting habitat for migratory birds. The refuge lands are both scenic and diverse, with approximately 4700 acres of habitats including sandy beach and dune, cranberry bog, ...
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  • Newbury, Massachusetts

    Hellcat Dunes Loop

    4.5
    0.98 mi / 20 ft gain
    Park in the parking area off of Refuge Rd. Take the Dunes Trail, a boardwalk path for the ~1-mile loop. Enjoy the views from an observation deck on three-story-high dunes. This trail is accessible from April-October.
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  • 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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  • Erving, Massachusetts

    Rattlesnake Loop to Red Trail

    1.97 mi / 676 ft gain
    Rattlesnake Loop to Red Trail is a loop trail that provides a good opportunity to view wildlife located near Erving, 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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  • 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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  • Newbury, New Hampshire

    Hike to Lake Solitude, NH

    4.0
    4.8 mi / 2510 ft gain
    The two most popular routes to Lake Solitude are the Newbury Trail and Andrew Brook Trail.  The round-trip distance of the hikes are 4.8 miles and 3.8 miles. Both could be described as moderate in terms of difficulty. The Newbury trail is accessed from Lakeview Ave and Andrew Brook Trail can be a...
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