Cheshire: Nature, Culture and Special Destinations

Cheshire combines expansive natural experiences with historic sites, art and a variety of trails. Those looking for a vacation rental as a base for different kinds of vacation days will find plenty of options here: protected landscapes, challenging hikes, museums, live productions and routes for cyclists offer a range of travel ideas. Whether you are planning an active day with your family, a cultural outing or a more relaxing visit to the countryside, your stay can be arranged in many different ways.

Nature Among Ponds, Forests and Rocky Gorges

In Cheshire County, Pisgah State Park protects seven ponds, four upland ridges and numerous wetlands in the towns of Winchester, Chesterfield and Hinsdale. The park has six access points and offers opportunities for hiking, mountain biking, ATV riding and snowmobiling year-round. This allows you to tailor your visit to your preferred activity without limiting the landscape to just one type of vacation.

Another distinctive landscape is Chesterfield Gorge, with rock walls up to 70 feet high. You can hike through the challenging terrain. If you would rather focus on water landscapes and wildlife viewing, you can choose the Appel Way Trail. It crosses the Ashuelot River and offers views of wetlands and wildlife along the entire route. The Anne Stokes Loop Trail in Madame Sherri Forest passes by Indian Pond.

Keene also offers space for outdoor activities. Greater Goose Pond Forest covers 1,044 acres and is Keene’s largest municipal open space. A conservation easement permanently protects the area while also supporting public access, recreation and education. Keene also has 8 miles of an improved rail trail and more than 40 miles of scenic singletrack trails for hiking and cycling.

Culture, History and Regional Discoveries

For a cultural day trip, the Wyman Tavern Museum offers insight into the past. The building was constructed in 1762 in the Georgian style and operated as an inn for 40 years. Tours and special events are available by appointment. In Keene, the Historical Society of Cheshire County offers tours of its exhibition galleries. The Thorne-Sagendorph Art Gallery on the campus of Keene State College displays works by students and professional artists.

The Colonial Theatre opened on January 29, 1924, and presents more than 120 live productions and film screenings per season. In 2004, it was added to the New Hampshire State Register of Historic Places. Harris Mill provides another cultural highlight and now houses the Weaving Center and the Harrisville Designs store.

Trails, Market and Choosing the Right Location

The Cheshire Recreational Rail Trail runs for 42 miles from Fitzwilliam through Troy, Keene and Westmoreland to North Walpole. An arched bridge over the Ashuelot River is one of its notable features. When choosing your accommodation, it may therefore be important to consider whether you primarily want to combine nature, culture or longer excursions. The Chesterfield Farmers’ Market takes place on Saturdays from 9 a.m. to noon on Main Street at Route 63 in Chesterfield. Stonewall Farm welcomes visitors to its farm, forests and trails.

If you are looking for accommodation in a specific town, you can narrow your selection to Keene, Swanzey, Jaffrey, Harrisville, Rindge, Chesterfield or Fitzwilliam. Another selection within the overview is Rockingham.

For the broader travel overview: New Hampshire.