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Cheshire Walkers 2024

We are so pleased to announce the Cheshire Walkers schedule for Spring 2024 - join us! Please see below for the schedule. This group is free and open to the public.

NOTE: Although we love dogs at the Conservancy, we ask that you keep them at home during Cheshire Walkers outings for everyone's safety and comfort.

To sign up for a walk, please click here and fill out the online form

Because parking is limited at many of our destinations, we ask that participants carpool whenever possible. To share a ride to the trailhead, please meet in the parking lot outside the Keene Department of Public Works/Keene Ice rink/Police Department (350 Marlboro St.) in time for a prompt 9:00 departure. Conservancy staff will help coordinate on most, but not all, mornings. If you are coming from downtown, turn left on Bartholomew Court after Butterfly Park, then take the first right into the first block of parking spaces. 

For more information, contact Kate Sullivan at


The Conservancy assumed leadership of the Cheshire Walkers in the fall of 2022. Originally founded and run by Cheshire Medical Center for decades, the Cheshire Walkers is a walking and hiking group for people of most abilities, with an emphasis on seniors and others who might prefer an easier pace. The walks provide an opportunity to exercise the body and the brain, offering participants spirited social interaction and opportunities to learn about the nature they are experiencing. 

Spring walks (some walks have yet to be confirmed, check back for more information)

Date: 4/16/24
Location: Sip Pond, Chamberlain Conservation Area, Fitzwilliam
Staff member leading the walk: Janine Marr
Will staff meet walkers to carpool: No
Description: Encompassing a quarter-mile of frontage on the southern shore of Sip Pond, the Chamberlain Conservation Area on the Cheshire Rail Trail provides fantastic wetland and pond views. We’ll follow the Cheshire Rail Trail from a trailhead on Old Turnpike Road to the Peninsula Trail, where pond ice was once loaded onto rail cars for transport to Boston. The trail leads to the tip of Chamberlain Point, where there are great views across the pond to Gap Mountain and Mount Monadnock. 
Round-trip distance: 2 miles
Breathing: Easy
Footing: Easy, except for a short section of rocky, uneven trail at the end of the peninsula.
Directions: From Keene, proceed south on Route 12 through Troy to Fitzwilliam. Continue south on Route 12 past the intersection with Route 119. 4.1 miles after crossing Route 119, turn right on Old Turnpike Road. Continue 0.7 miles on Old Turnpike Road; the trailhead parking is on the right, marked with a sign. Parking is plentiful.

Date: 4/23/24
Location: Widow Gage Town Forest, Fitzwilliam
Staff member leading the walk: Richard Pendleton 
Will staff meet walkers to carpool: No
Description: Widow Gage Town Forest is managed by the Fitzwilliam Conservation Commission and has been protected by a Monadnock Conservancy conservation easement since 2009. The blue trail is a 1-mile lollipop over easy to moderate terrain (due to roots and rocks). We can stop at the beaver pond (about 0.3 miles) and the Whitcomb cellar hole (about 0.5 mi). There are lots of stone walls, a huge rock pile, and an interesting, curved wall along the trail. 
Round-trip distance: 1 mile 
Breathing: Moderate
Footing: Moderate 
Directions: From Keene, take Route 12 south to Route 119 in Fitzwilliam. Turn right onto Route 119, pass through the village, and continue for one mile to a right turn onto Rhododendron Road. Continue 3.1 miles on Rhododendron Road (past Rhododendron State Park; note the road will become gravel) to the Town Forest parking area and trailhead on the right.

Date: 4/30/24
Location: High Blue/Warner Forest & Scovill Town Forest, Walpole
Staff member leading the walk: Ryan Owens
Will staff meet walkers to carpool: Yes
Description: Walpole is known for its farms, but its forests are beautiful, too. These properties, owned by the Society for the Protection of NH Forests and the Town of Walpole, respectively, feature views of the Green Mountains and the highest point in the town, all connected by a trail through rolling forest and mossy glades. 
Round-trip distance: 2.5 miles
Breathing: Moderate
Footing: Moderate to hard due to sections of rocky, uneven trail. 
Directions: From downtown Keene, take Court Street north to the Maple Ave./Route 12A traffic circle, where Court Street becomes Old Walpole Road. Continue straight on Old Walpole Road 5.8 miles, then turn right on Crehore Road. At the T intersection, turn left on Merriam Road, then take the next right on Scovill Road. Continue 0.4 miles to where Scovill Road becomes unmaintained, just before the large TV antenna. There is no designated parking, so park anywhere out of the way, including beneath the TV antenna, taking care not to block driveways or gates. Parking is limited, so please carpool. 

Date: 5/7/24
Location: Tippin Rock, Swanzey
Staff member leading the walk: Alex Metzger
Will staff meet walkers to carpool: Yes
Description: Come for the gorgeous views, stay to learn the secret technique for making a massive glacial erratic boulder sway with your bare hands! We’ll walk from a sunny hayfield through a hemlock forest and on to the top of Hewes Hill, passing the iconic rock along the way. Though the climb to the Rock is steadily uphill, it is scarcely 0.7 miles (one way), and the footpath itself is smooth. 
Round-trip distance: 1.8 miles
Breathing: Moderate due to the steady uphill climb.
Footing: Easy
Directions: From Keene, take Route 12 south and turn right on Route 32 (Old Homestead Highway) toward the Keene Airport. Pass the airport and continue south on Route 32 through the traffic circle, passing Monadnock High School. Turn right onto Warmac Road 3.4 miles after the traffic circle. The trailhead is 0.5 miles ahead on the left, opposite Chebaco Kennels. Parking is limited to a few spaces in front of the gate and along the road.

Date: 5/14/24
Location: Kroka, Marlow
Staff member leading the walk: Pete Throop
Will staff meet walkers to carpool: Yes
Description: Kroka Expeditions is a non-profit wilderness expedition school based on a year-round organic farm in Marlow. Diverse offerings range from week-long programs in Marlow to an annual semester expedition from the Canadian Arctic to New York City by ski and canoe. Kroka welcomes visitors to its network of public trails on the Marlow campus. We’ll explore the property, visiting a beaver pond and Porcupine Cliffs, and see some of the rustic structures that students call home in all seasons. Though not long, this is a more challenging walk due to sections of the trail with poor footing, including stepping up and down boulders and crossing streams on rocks. 
Round-trip distance: 1.5 miles 
Breathing: Moderate 
Footing: Hard
Directions: From Keene, proceed north on Route 10 for 5.8 miles, then turn left onto Main Street in Gilsum, which becomes Alstead Hill Road and then Gilsum Mine Road. Follow this road for 4.2 miles to Route 123 in East Alstead. Turn right. The Kroka Trailhead parking lot will be 1.2 miles on your right; look for a prominent trailhead sign. If you reach the Kroka headquarters/farmhouse, you’ve gone too far. There is ample parking.

Date: 5/21/24
Location: Sunset Hill, Dublin
Staff member leading the walk: Anne McBride
Will staff meet walkers to carpool: No
Description: This 590-acre private property in Dublin was protected in 2022. Our loop hike begins on a dirt town road before we traverse old woods roads through a forest and on to a gorgeous hilltop view of Mt. Monadnock. On our return, there will be a point where we will leave the woods road and bushwhack for about 500 feet to join the Monadnock-Sunapee Greenway Trail to return to our point of beginning. 
Round-trip distance: 1.9 miles
Breathing: Moderate
Footing: Moderate to hard due to roots and rocks. If it's been a wet spring, be prepared for some mud.
Directions: Due to extremely limited parking, we will meet at the parking lot of the Dublin Lake Club Golf Course ( and carpool from there. From Keene, head east on Route 101 for 8.4 miles. Turn right onto Charcoal Road and continue for 1 mile to a T intersection. Turn left onto Old Marlborough Road. The dirt parking area will be 0.1 miles on your right (just before the junction with Old Troy Road). The golf course will be across the road.

Date: 5/28/24
Location: Friedsam Town Forest, Chesterfield
Walk leaders: Tom Duston (Monadnock Conservancy Lands Committee) and Lynne Borofsky (Chesterfield Conservation Commission)
Staff member on the walk: Kate Sullivan
Will staff meet walkers to carpool:No
Description: The Friedsam Town Forest is a 220-acre jewel donated by the Friedsam Family to the Town of Chesterfield managed by the Chesterfield Conservation Commission and a very active group of volunteers. Our hike will take us through varied terrain of old stone walls, ancient trees, an old apple orchard, quartz outcroppings, rushing brooks, and ravine views with a new bridge. One can see what happens to old farmland pastures after several years of non-use.
Round-trip distance: 2 miles (1.5 - 2 hours)
Breathing: Occasionally moderate to hard   
Footing: Moderate with some hard with ups and downs, expect some muddy areas. 
Directions from Keene Monadnock Marketplace: go West on Rte 9 for 9.7 miles to Twin Brook Road on your left.
Travel Twin Book Road for 0.2 miles and turn left into Lower Lot.
(From Brattleboro/Chesterfield Bridge: go East 4.4 miles to Twin Brook)

Date: 6/4/24
Location: Beech Hill, Dublin
Staff member leading the walk: Ryan Owens
Will staff meet walkers to carpool: Yes
Description: Dublin's Beech Hill, overlooking Dublin Lake, is the former site of a substance use disorder hospital. Following a period of decline and the hospital's closure, the land was purchased in 2006 by the Beech Hill-Dublin Lake Watershed Association in partnership with the Monadnock Conservancy. The buildings were subsequently demolished and the site restored to a meadow. Now permanently protected by a conservation easement held by the Conservancy, Beech Hill and its many trails are open to the public. Following a loop through forest and meadow, we'll take in the easterly views from Eagle Rock and a commanding vista of Mount Monadnock from the South Outlook. 
Round-trip distance: 2 miles
Breathing: Moderate to hard due to a few steep pitches
Footing: Hard due to sections of rocky, uneven trail. 
Directions: From Keene, take Route 101 east 11.5 miles to Dublin. Just before the rotary in Dublin's village, turn left onto Dublin Road/New Harrisville Road. Continue 0.5 miles to Beech Hill Road on the left. Climb Beech Hill Road 0.2 miles to the trailhead and gate. The road can be rough, but there is ample parking.