Berkshire Natural Resources Council Bob's Way

Route 23, Monterey, MA

About Bob's Way

Bob's Way, located on Route 23 in Monterey, is a 263-acre reserve with two hiking loops through a serene natural environment. These loops provide up to 2.5 miles of easy-to-moderate hiking that can engage both casual walkers and avid hikers. Whether exploring the property's wetlands, mixed woods, or its many historical remnants, visitors can experience a diverse Western Massachusetts landscape with rolling hills sheltered by surrounding water. A beaver pond to the southwest harbors abundant wildlife viewing opportunities with porcupines, otters, beavers, and other mammals roaming the area. Those looking to explore plant life will find a thriving northern hardwood forest scattered with mountain laurel, which lights up the property in white, pink, and purple during peak blooming season. Excellent birding is available throughout the property.

The hiking trails at Bob's Way form a figure-8 shape, with each loop a bit over a mile long. While the inner and outer loops have similar scenery, the outer loop meanders past the beaver pond and additional wetlands not seen on the inner loop. Between these loops is the Truman Dowd Crossing, a flat, mellow trail that allows hikers to connect across the eastern and western sides of the property. This connection can also be formed with the Cathcart Crossing, which climbs 100 feet to Dave's Bench, a stone-sculpted seating area that overlooks the surrounding forest.

The trail system is well-marked, maintained, and suitable for use at all times of year. Snowshoeing and cross-country skiing are popular activities after a heavy snowfall, as the terrain at Bob's Way offers enough variation to work up a sweat but not so much as to make these activities exhausting. In the fall, the forest glows in red and yellow, making Bob's Way an excellent stop on a leaf peeping trip in the Berkshires.

Visitors can access the site from the parking lot on Route 23. The trailhead is marked with a rock reading "Bob's Way," and an informational kiosk rests a short distance into the woods. According to the Berkshire Natural Resources Council, which manages the site, Bob's Way is named after one of the greatest conservationists in Massachusetts history, N. Robert Thierot. His son chose the name to recognize that "with Bob, there was only one way. And it was always Bob's way."