Five Hikes Challenge - Hike List

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Use this page to help you figure out which hikes you'd like to tackle in the 2020 Five Hikes Challenge! All hike mileages below are ROUND TRIP.  Click on property names to see the Reservations Guide pages for these properties, with additional information and photos to help you deicide! After registering for the challenge, you'll be mailed print maps for your selected hikes. Happy hiking! To return to the registration page for the 2020 Five Hikes Challenge click HERE.  


  • Dame Forest (Sweet Trail), Durham  
    • Easy 1.8 mile out-and-back hike with nice wetland views and hemlock forests
  •  Champlin Forest, Rochester 
    • Easy 2 mile hike, pine forest, fields, and wetlands
  • Creek Farm, Portsmouth
    • Easy 1.5 mile loop with shoreline views of Sagamore Creek, salt marsh, and historic mansions



  • Heald Tract, Greenville/Mason/Temple/Wilton 
    • Easy 1.6 mile hike adjacent to wildlife pond, or moderately strenuous 4.0 mile loop with beaver pond, varied habitats
  • High Five, Deering 
    • Easy 0.7 mile climb on woods road to spectacular panoramic views
  •  McCabe Forest, Antrim 
    • Easy 1.7 mile hike, partially along Contoocook River 
  • Madame Sherri Forest, Chesterfield  
    • Moderately strenuous 2 mile loop to scenic Indian Pond and/or easy 0.2 mile hike to remnants of Madame Sherri’s “castle”
  •  Hedgehog Mountain, Deering  
    • Moderate 1.2 mile round trip climb to ledges on Hedgehog Ridge, views of Contoocook Valley
  • High Blue, Walpole  
    • Moderate 2.4 mile hike to highest point in Walpole, beautiful fields, vernal pool, several viewpoints
  •  Gap Mountain Reservation (North Trail), Jaffrey/Troy  
    • Strenuous 2.4 mile round trip climb to rocky summit of Gap Mountain, great views of Mount Monadnock


  • Ashuelot River Headwaters Forest, Lempster  
    • Moderate 1.2 mile climb to summit of Silver Mountain, panoramic views of nearby mountains
  • Langenau Forest, Wilmot 
    • Moderate 2 mile loop through mixed forest types, beaver pond, streams, views of Mount Sunapee
  • Andrew Brook Forest, Newbury  
    • Strenuous 3.8 mile round trip climb along Andrew Brook to beautiful Lake Solitude on the eastern slope of Mount Sunapee
  • Hay Reservation, Newbury  
    • Moderately strenuous 2.4 mile round trip climb to summit of Sunset Hill, views of Lake Sunapee and old cellar holes


  • Morse Preserve, Alton 
    • Moderate 1.7 mile hike to fantastic views of Lake Winnipesaukee and White Mountains
  • Moody Mountain, Wolfeboro  
    • Easy 1.4 mile rolling trail through old field white pine, spruce, beech and red oak - once a former pastureland
  • Cockermouth Forest, Groton/Hebron  
    • Strenuous 3.6 mile round trip climb on trails and woods roads to Bald Knob, great mountain views
  •  Eagle Cliff Forest, Sandwich  
    • Strenuous, steep 1.2 mile climb to overlook with fantastic views of Squam Lake
  •  Cooper Cedar Woods, New Durham  
    • Easy 0.7 mile walk, partially on boardwalks, through rare Atlantic Cedar Swamp habitat
  •  Moose Mountains, Brookfield/Middleton  
    • Moderately strenuous 2.5 mile round trip climb on trails and woods roads to summit of Phoebe’s Nable Mt, beautiful views, former farm fields
  • Weeks Woods, Gilford  
    • Easy to moderate 2 mile hike on old logging roads and trails, fields, forests


  • David Dana Forest, Dalton  
    • Moderately strenuous 1.5 mile hike to entrance of an abandoned gold mine
  • Bretzfelder Park, Bethlehem 
    • Easy 0.5-2 mile hikes, interpretive nature trails and picnic area by wildlife pond