25 Self-Guided Hikes in Western MA

Self-Guided Hikes in Western Massachusetts

Bullitt Reservation in Ashfield, MA (c) Sienna Wildfield

Bullitt Reservation in Ashfield, MA. (c) Sienna Wildfield

The following is a list of places to discover in your community with friends, family, or on your own. Before exploring, become aware of the literary, artistic, and historic connections that some of these places offer.

Easy Hikes in Western MA:

  • Chesterfield Gorge, West Chesterfield
  • Dinosaur Footprints, Holyoke
  • Field Farm, Williamstown
    Field Farm features a garden with 13 modern sculptures, including works by artists Henry Ferber and Richard M. Miller. For architecture enthusiasts, the artistic play between Field Farm and The Folly’s mid-century design elements and the natural landscape surrounding them is compelling.

Moderate Hikes in Western MA:

  • Bear Swamp, Ashfield
  • Bear’s Den, New Salem
  • Bullitt Reservation, Ashfield
  • Chapel Brook, Ashfield,
  • Land of Providence, Holyoke
  • Little Tom Mountain, Holyoke
  • Dry Hill, New Marlborough
  • McLennan Reservation, Tyringham
  • Mt. Warner, Hadley
  • Mountain Meadow, Williamstown
  • Notchview, Windsor
  • Questing, New Marlborough
  • Tyringham Cobble, Tyringham
  • Bradley Sanctuary, Williamsburg
  • Breckenridge Sanctuary, Williamsburg
  • William Cullen Bryant Homestead, Cummington
    At the William Cullen Bryant Homestead explore old growth forest on the Rivulet Trail. This same woods inspired Bryant to write his 1823 poem “The Rivulet.” This poem and other nature poetry by Bryant are placed on interpretive displays along the trail for visitors to read. Bring along your notebook to contribute your own poetic musings too!
  • Bartholomew’s Cobble, Sheffield
    Take the trail that leads you to the historic Ashley House, listed in the National Register of Historic Places, a significant site of the Upper Housatonic Valley African American Heritage Trail. Elizabeth Freeman, also known Mum Bett, enslaved in the Ashley House, was the first black slave to successfully sue for and win her freedom.

Strenuous Hikes in Western MA:

  • Glendale Falls, Middlefield
  • Monument Mountain, Great Barrington
  • Peaked Mountain, Monson
  • Petticoat Hill, Williamsburg
  • Skinner State Park, Hadley
    Hike the Holyoke Range and to the top of Mt. Holyoke’s summit. This mountain features a summit house at the top and incredible views of the Connecticut River Valley. It was also the summit scene that Thomas Cole painted in his famous 1836 painting of the Connecticut River Oxbow. Thomas Cole and William Cullen Bryant were great friends and their literary and artistic works helped to inspire the early start of the American land conservation movement. Although Cole’s painting is at the Metropolitan Museum of Art, the mountain and the same inspiring view are here right in the Pioneer Valley!

Excerpt from Learning Ahead: Cultural Itinerary for Western Massachusetts (Seasons: Sept/Oct), a downloadable bimonthly publication produced by Hilltown Families that sheds light on embedded learning opportunities found in cultural resources that exist within the geography, history, and cultural traditions of Western Massachusetts.




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