Discover Cheshire

Discover Cheshire through its varied landscapes, trails and cultural offerings. Ponds, highland ridges and wetlands define its natural side; museums, theaters, galleries and a farmers’ market offer more ideas for planning your trip. Which places you focus on depends on whether you mainly want to spend time outdoors or experience history and culture.

Nature and Trails

In Cheshire County, Pisgah State Park in the towns of Winchester, Chesterfield and Hinsdale protects seven ponds, four highland ridges and numerous wetlands. The park has six trailheads, as well as opportunities for hiking, mountain biking, ATV riding and snowmobiling. This offers options ranging from hikes to motorized and winter activities. Mount Monadnock, also called Grand Monadnock, is a 3,165-foot mountain in the town of Jaffrey, New Hampshire.

Chesterfield Gorge is a rocky gorge with cliff walls up to 70 feet high. In the recreation area, you can hike challenging terrain. Other nature experiences have their own highlights: the Appel Way Trail crosses the Ashuelot River and offers views of wetlands and wildlife along the entire route. In Madame Sherri Forest, the Anne Stokes Loop Trail passes scenic Indian Pond.

Greater Goose Pond Forest covers 1,044 acres and is Keene’s largest municipal open space. A conservation easement permanently protects the forest; its management plan supports public access, recreation and education. Several route details can also help you plan days of cycling and hiking: the Cheshire Recreational Rail Trail runs 42 miles from Fitzwilliam through Troy, Keene and Westmoreland to North Walpole. One of its features is an arched bridge over the Ashuelot River. Keene has 8 miles of improved rail trail, as well as more than 40 miles of scenic singletrack trails for hiking and cycling. When planning, pay attention to the type of trail and its length.

History and Culture

The Wyman Tavern Museum tells the story of a Georgian-era building: Wyman Tavern was built in 1762 and operated as an inn for 40 years. Tours and special events are available by appointment; arrange your visit with the museum in advance.

The Colonial Theatre in Downtown Keene opened on January 29, 1924, and was added to the New Hampshire State Register of Historic Places in 2004. Each season, the theater presents more than 120 live productions and film screenings. If you’re planning to attend a performance, check the dates on the current season’s schedule. This makes it easier to coordinate a theater visit with the other stops on your trip.

Other cultural attractions showcase different sides of the region: the Thorne-Sagendorph Art Gallery on the Keene State College campus displays work by students and professional artists. The Historical Society of Cheshire County offers tours of its exhibition galleries. Harris Mill is now home to the Weaving Center and the Harrisville Designs shop.

A Market Visit in Chesterfield

The Chesterfield Farmers’ Market is held Saturdays from 9 a.m. to noon on Main Street at Route 63 in Chesterfield. As the schedule may change seasonally, check the dates before your visit. The market adds a regular weekly time to your trip plans; theater schedules and museum visits, by contrast, follow their own programs or require an appointment.

Discover More Destinations

Discover more destinations: Swanzey, Keene, Jaffrey, Harrisville, Rindge, Chesterfield, Fitzwilliam, Coos.

For the broader travel overview: New Hampshire.