Brought to you by Cheshire Medical Center

While Pitcher, Gap, and Monadnock are popular mountains to hike, our region also offers many delightful walks that are more accessible to all ages and abilities. So grab a friend, neighbor, or coworker and go for a quick stroll — or pack up a picnic and make a day of it!

Keene:  Cheshire Rail Trail over the North Bridge

Footing:  Easy    Breathing: Easy   Start at:  Park at the CVS / Panera lot; the trail runs behind the buildings.

Walk West to the North Bridge over Rt 9/10/12. On the other side, you will find fields full of evening fireflies in the summer. Keene Country Club is 1.5 miles and Stonewall farm 3 miles down the trail.

Keene:  Ashuelot Rail Trail over the South Bridge

Footing: Easy   Breathing: Easy Start at:  the Emerald St side of the Center at Keene parking lot. The trail starts at the wooden railings near Ralston St.

From The Center at Keene, find the trail running past Keene State College and over the new South Bridge. The Keene State Athletic Fields are 1 mile and Ash Swamp Brook 1.5 miles down the trial. It is a good idea to bring bug spray once the mosquitoes arrive.

Keene:  Robin Hood Park 

Footing: Moderate  Breathing: Moderate, some uphill  Start at: Robin Hood Park, 366 Reservoir St., Keene.

Take the trail through Robin Hood Park, past the reservoir and through the woods. A maze of trails crisscross this forested park which is set back into a west-facing hillside with a pond, ledges and massive boulders to explore. A small stream cascades into the pond and there is a picnic area close to the parking lot.

Keene:  Wheelock Park — Appel Way Trail

Footing: Easy Breathing: Easy/moderate  Start at:  Park at Wheelock Park off Park Ave in Keene, the trail head is on the lot across from the pool.

The Appel Way Trail is a 1 ¼ mile paved bike path connecting Wheelock Park to Court St. It winds over Rt 12, under Rt 9, then across the Ashuelot River. You can also extend this walk by turning right after crossing the river and taking the Jonathon Daniels Trail 1 mile along the river to Ashuelot Park.

Jaffrey:  Monadnock Branch Rail Trail

Footing: Easy  Breathing: Easy  Start at:  8 Blake St. The parking lot behind Jaffrey Pizza Barn. The trail is across the road, then turn right/South.

This easy-going walk along the beautiful Contoocket River spans just over 2 miles. If you visit in early June, the abundant lady slippers that grow along the trail will be in bloom! There is a public boat launch at Old County Road and just beyond you will find the Contoocook Marsh Conservation Area which offers a small trail loop and benches to enjoy the scenery and wildlife at the wetland’s edge.

Walpole/Alstead:  Distant Hill Gardens & Nature Trail

Footing: Easy  Breathing: Easy  Approximate Length:  2miles  Start at: Distant Hill Nature Trail, 66 March Hill Road, Alstead.

Explore the new Distant Hill Nature Trail, a mile-long wheelchair-accessible trail just East of the gardens. The trail winds through a hemlock/beech forest with several unique wetlands, including five vernal pools and a forest seep. There is also a short boardwalk over an uncommon quaking cranberry bog. https://www.distanthillgardens.org/distant-hill-nature-trail/.

Chesterfield:  Chesterfield Gorge

Footing: Hard    Breathing: Moderate/Hard   Start at: Chesterfield Gorge, 1823 Route 9, Chesterfield

The ¾ mile loop trail leads to the falls and cascades as Wilde Brook flows through Chesterfield Gorge. Although this walk is not very long, there are several steep sections with uneven footing, so take your time and bring hiking poles if you use them.   

West Chesterfield: Hike Along the Connecticut River

Walking:  Moderate  Breathing:  Moderate   Start at:  Turn left on Gulf Rd just before the Rt 9 bridge into Brattleboro from Keene. Then follow the dirt Mountain Rd to the end for parking.

Take a scenic hike along the river enjoying the gorgeous views of Vermont and the entire tri-state region. It is 1.2 miles to the base of Wantastiquet Mountain Natural Area, where you could continue hike right up to the top.


The Cheshire Walkers have been meeting for 20 years every Wednesday to take walks like these together through this program of the Center for Population Health at Cheshire Medical Center. They have explored 240 different trails so far!

 To join or learn more, call (603) 354 5454×2791, visit health-wellness.cheshiremed.org/Cheshire-walkers-program or pick up a program of events from Cheshire Medical Center.