We are so pleased to announce the Cheshire Walkers schedule for Fall 2025 - join us! Please see below for the schedule. This group is free and open to the public.
NOTES:
Please arrive to the walk location by 9:15am, walks will begin at 9:30am.
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.
For this season, we will not be meeting walkers at the Department of Public Works in Keene. Hikers are welcome to meet on their own and carpool and our team will meet you at the trailheads. If you are planning on meeting at DPW, we suggest you arrive there by 8:45am.
To sign up for a walk, please click here and fill out the online form.
For more information, contact Kate Sullivan at kate@monadnockconservancy.org.
Background
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.
Fall walks
Date: 09/16/25
Location: Cranberry Meadow Pond Trail, Peterborough
Walk leader: Evan Walsh, Interpretive Ranger with the Student Conservation Association, New Hampshire Conservation Corps
Will staff meet walkers to carpool: No
Description: The Cranberry Meadow Pond Trail is a favorite dog-walking trail that connects downtown Peterborough to the summit of Pack Monadnock. We will walk the one-mile section from Old Street Road to Cranberry Meadow Pond. This section of trail meanders through a wetland via a boardwalk and hemlock-cooled woods, then along a brook for nearly 1/2 mile before climbing uphill slightly to an area where mature white pines and highbush blueberry bushes overlook Cranberry Meadow Pond. The trail contains some footbridges, roots and rocks in a few places, and a small hill; however, we will walk it slowly so that everyone can negotiate the trail easily and safely.
Round-trip distance: 2 miles
Breathing: Easy to moderate (along small hill)
Footing: Easy to moderate (step through stone wall, step up onto boardwalk and bridge, small hill incline)
Directions: GPS address 49 Old Street Road, Peterborough. From 101 and 202 intersection in downtown Peterborough: East up hill .9 miles. Take left at blinking light. Roadside parking .2 miles on right. (After Cranberry Meadow Pond Farm Inn on corner (Inn = #5 Old Street Road; parking across from gated driveway #24). Meet at kiosk at entrance to trail. (If you drive too far north, you'll go through a stop sign and later see the parking area for the Shieling Forest trails on the right.)
Date: 09/23/25
Location: Cunningham Pond, Peterborough
Walk leader: Richard Pendleton
Additional staff member on the walk: Amanda Littleton, Jen Weimer
Will staff meet walkers to carpool: No
Description: Peterborough’s former public water supply and now site of the town beach, Cunningham Pond is a jewel perched high above the town in the shadow of Pack Monadnock. The main two-mile loop traverses woodlands and a hemlock grove, crossing two streams on sturdy wood bridges. Then, it climbs to a large hay field with sweeping views. From the field, the trail continues down to an old carriage road, following the pond’s edge before looping back to the main trail. The terrain is generally rolling, with only short steeper sections, and the surface is a mix of flat sections and some portions that require stepping over rocks and roots.
Round-trip distance: 2 miles
Breathing: Moderate
Footing: Moderate
Directions: Carpooling is a must, as parking is limited to 4-5 cars, with no spillover options. From Keene, head east on Route 101 to Peterborough. Continue uphill on Route 101 past the intersection with Route 202 for 2 miles, then turn left onto Cunningham Pond Road. Continue for 0.8 miles on Cunningham Pond Road to the trailhead on the right, soon AFTER the town beach and residence on the right. NOTE this is not the location of the town beach.
Date: 09/30/25
Location: Calhoun Family Forest, Gilsum
Walk leader: Janine Marr
Additional staff members on the walk: Lacy Gillotti, Joy Fletcher
Will staff meet walkers to carpool: No
Description: This meandering one-way trail on the John and Rosemarie Calhoun Family Forest travels through a mixed hardwood-conifer forest rich with mosses and ferns. The trail follows White Brook, a quintessential babbling brook that makes a peaceful backdrop for a picnic, and culminates at a bridge over the brook — a wonderful spot to enjoy “Porky Falls” as the Calhoun family called this waterfall.
Round-trip distance: .4 miles
Breathing: Moderate
Footing: Moderate
Directions: From Routes 10/12/9E: Head north on Route 10 towards Gilsum. Go 5.1 miles and turn right onto White Brook Road. Follow the road to the end where there is a gate and a parking area. From the north: Follow Route 10 south through Gilsum center. It is 7.3 miles from the intersection of routes 10 and 123 to White Brook Road. Turn left on White Brook Road. Follow the road to the end where there is a gate and parking area.
Date: 10/7/25
Location: Widow Gage Town Forest, Fitzwilliam
Walk leader: Jen Weimer
Additional staff members on the walk: Joy Fletcher and Martin Royle
Will staff meet walkers to carpool: No
Description: Widow Gage Town Forest is managed by the Fitzwilliam Conservation Commission and 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 mile) and the Whitcomb cellar hole (about 0.5mi). There are lots of stone walls, a huge rock pile, and an interesting curved wall along the trail.
Round-trip distance: 1 mile
Breathing: Easy
Footing: Easy
Directions: From Route 101/Route 12 traffic lights in Keene, take Route 12 South to Lower Troy Road, Fitzwilliam (opposite AB Tech on left). Bear right onto Lower Troy Road, drive 0.5m. Stay straight onto Upper Troy Road (caution: traffic from left does not stop) until stop sign. Make an immediate right turn (at Fitzwilliam Inn) onto Richmond Road in the center of Fitzwilliam. Drive 0.7m to Rhododendron Rd (Stop sign). Turn right and drive 2.9m on Rhododendron Rd (past Rhododendron Park; note the road will be come gravel) to the parking area and kiosk on the right.
NOTE: LOCATION HAS CHANGED FOR THE LAST WALK
Date: 10/14/25
Location: Beech Hill, Dublin (formerly Sip Pond)
Walk leader: Anne McBride
Additional staff members on the walk: Lindsay Taflas and Kate Sullivan
Will staff meet walkers to carpool: No
Description: This recently finished, fully accessible trail, is about a mile from end to end, circles the meadow and includes an expansive overlook of the Contoocook Valley, Crotched Mountain and the Wapack range.
Round-trip distance: 1 mile
Breathing: Easy
Footing: Easy
Directions: From Keene, take Route 101 east 11.5 miles to Dublin. Just before the Dublin Fire Department 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.