2023 Five Hikes Challenge - Hike List

Use this page to help you figure out which hikes you'd like to tackle in the 2023 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 2023 Five Hikes Challenge click HERE.  

P.S. Looking for a list of just the easiest trails? Click here. While we don't have any all-access trails at this point, there are many flatter trails with benches.

SEACOAST REGION

Easy 1.8 mile out-and-back hike with nice wetland views and hemlock forests

Easy 2 mile hike, pine forest, fields, and wetlands

Easy 1.5 mile loop with shoreline views of Sagamore Creek, salt marsh, and historic mansions.

 

MERRIMACK VALLEY REGION

Easy 1.5 mile walk along Merrimack River, silver maple floodplain forest, and wetland habitats, plus benches for views or resting.

Easy 2-3 mile walk, cultural history of abandoned colonial settlement, nice wetland and field views, plus benches.

Strenuous 3 mile round trip hike to nice views from Mount Wallingford through wetlands.

 

MONADNOCK REGION

Moderate hike along the Silver Mountain Trail that is 1 mile, round-trip, with dramatic westward views overlooking Lempster and the Connecticut River Valley beyond

Easy 1.6 mile hike adjacent to wildlife pond, or moderately strenuous 4.0 mile loop with beaver pond, varied habitats

Easy 0.7 mile climb on woods road to spectacular panoramic views

Easy 1.7 mile hike, partially along Contoocook River 

Moderately strenuous 2 mile loop to scenic Indian Pond and/or easy 0.2 mile hike to remnants of Madame Sherri’s “castle”

Moderate 1.2 mile round trip climb to ledges on Hedgehog Ridge, views of Contoocook Valley

Moderate 2.4 mile hike to highest point in Walpole, beautiful fields, vernal pool, several viewpoints

Strenuous ~2.5 mile round trip climb to rocky summit of Gap Mountain, great views of Mount Monadnock. Two options for reaching the summit- either north trail, or south, similar difficulty.

The Dublin Trail is a very strenuous climb for experienced hikers only. 4.4 miles.

This moderate, 2-mile trail includes a stop at the Black Heritage Trail of New Hampshire marker installed in 2021 to honor the family of James Due. The Dues were one of the first African American families to settle in Hancock in the 1700s, and were subject to many prejudices.

 

DARTMOUTH/LAKE SUNAPEE REGION

Moderate 2 mile loop through mixed forest types, beaver pond, streams, views of Mount Sunapee

Strenuous 4 mile round trip climb along Andrew Brook to beautiful Lake Solitude on the eastern slope of Mount Sunapee

Moderately strenuous 2.4 mile round trip climb to summit of Sunset Hill, views of Lake Sunapee and old cellar holes

Moderately Strenuous to Strenuous for length and steepness - a steady climb along the Lincoln Trail on woods roads and narrow forest trails to a nice lookout at Baker's Ledge, 4.2 miles round trip.

 

LAKES REGION

Moderate 1.7 mile hike to fantastic views of Lake Winnipesaukee and White Mountains

Easy 1.4 mile rolling trail through old field white pine, spruce, beech and red oak - once a former pastureland

Strenuous 3.6 mile round trip climb on trails and woods roads to Bald Knob, great mountain views

Strenuous, steep 1.2 mile climb to overlook with fantastic views of Squam Lake

Easy 0.7 mile walk, partially on boardwalks, through rare Atlantic Cedar Swamp habitat

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

Easy to moderate 2 mile hike on old logging roads and trails, fields, forests

Strenuous 3.3 mile hike with some rock scrambling to reach stunning views of Lake Winnipesaukee and White Mountains beyond.

Strenuous 3-mile hike that climbs up the southeast side of Green Mountain. 

 

WHITE MOUNTAINS & NORTH COUNTRY​

The Forest Society's newest reservation hosts a short trail that is .90 mile, roundtrip, and accesses the Ammonoosuc River.

Moderately strenuous 1.5 mile hike to entrance of an abandoned gold mine

Easy 0.5-2 mile hikes, interpretive nature trails, wildlife viewing at pond, and covered picnic area. 

  • Lost River Reservation, North Woodstock- * NOTE: LOST RIVER GORGE AND TRAIL ENTRANCE CLOSE AFTER OCTOBER 15**

The Kinsman Notch Ecology Trail is a half-mile loop of easy to moderate hiking difficulty. *Want to go inside the gorge? Select this hike and you will receive a free ticket to Lost River Gorge & Boulder Caves! (Note that new members receive two free passes when they join.)*

 

To return to the registration page for the 2023 Five Hikes Challenge click HERE.  

Recreation