The Berkshires Blog

Fifteen Great Hikes In & Around the Berkshires

Fifteen Great Hikes In & Around the Berkshires


Benedict Pond Loop- Wooded 2 mile trail around a pleasant mountain pond with swimming available at the same location. Take 20 east to 102 west, about 2 ½ miles to a left on Meadow Rd., then turn right on Pine St. to Beartown Mountain Rd. Continue about 5 miles On a rough state forest road to the Pond. (Monterey & Great Barrington) Note: use main entrance for better roads.

Canoe Meadows- Walk along graded roads & wooden walkways through a wildlife preserve owned by the Audubon Society. Up to 3 miles. Go west on 20 about 7 miles to a right
turn on Holmes Rd., just past the Mobile station. Follow Holmes Rd. for about 2 ½ miles & watch for signs on the right. (Pittsfield) Note: there is a fee.

• October Mountain Loop Trail- 1mile loop through forest near the campground. Excellent with small children. Take 20 west ½ mile to right on Center St., then bear left on Columbia St. Watch for signs to State forest at Bradley St. in about 1 mile. (Lee)

• Olivia’s Lookout- Short quarter mile hike to two excellent lookout spots, east & west. Take 20 west to 183 south to Richmond Rd. just past the main gate at Tanglewood. Continue about 1 mile up the hill to a parking area on the left. (Lenox, West Stockbridge, Richmond)

• Pleasant Valley Wildlife Sanctuary-Series of nature trails of various lengths Suitable for children & the handicapped. Upper trails offer longer distances, steep terrain & excellent views from Lenox Mountain. Take 20 west about 2 miles & turn left on West Dugway Rd. just past Bennigan’s Restaurant. Continue about 1 ½ miles to the sanctuary. (Lenox) Note: there is a fee.

• Tyringham Valley Floor- Two mile hike through woods & on wooden walkways on the famed Appalachian Trail. Hike across valley & back with excellent views. Take 20 east to 102 west to left on Tyringham Center & turn right on Jerusalem Rd. Drive up a short hill & watch for gas pipeline crossing. Park by the road & look for white blazed trail on steps over a stone wall on left side of the road. Walk about one mile to Main Road & return.(Tyringham)


Basin Pond- Wooded walk to breached dam, which twice failed causing loss of life & property. About 3 ½ miles. Take 20 east about 4 miles to Becket Rd. Turn left & go up hill about ¼ mile to a parking area on the left. Signs point to the red blazed trails. (Lee)

• Finnerty Pond- Walk old wood roads to an unspoiled mountain pond at an intersection with the Appalachian Trail. About 2 miles each way. Take 20 east about 4 miles to Becket Rd. Turn left & go up the road to a small parking area by a yellow gate. Trail is easy to follow with one major intersection, where you will bear right. (Becket & Washington)

• Historic Becket Quarry- See an outdoor museum at a quarry abandoned in the 1960’s with much of the original equipment still in place, including the derrick, winches, old trucks, building, small rail cars, & railroad track. Hike about 1 mile from the parking area, more to see other areas of the quarry. Take 20 east about 14 miles to the intersection with Route 8 north. Turn right on Bonny Rigg Hill Rd. Continue about 1 ½ miles to a left & Quarry Rd. & Continue about 1 mile to the quarry parking area. (Becket)

• Schermerhorn Gorge- Hike past cascading water to Felton Pond & return. Take 20 west to a right on Center St. Bear left at Columbia St. & watch for October Mountain State Forest signs at Bradley St. Go past the campground & reach Woods Pond on your left. Turn right & continue on your left. Turn right & continue on a very rough dirt road called Woodland Rd. for ½ mile to a small parking area. Follow the blue blazes up past the cascade to the pond. Come down the opposite side of the falls for a different view. (Lee & Washington)

• Stone Arch Bridge Trail- View scenic & durable bridges built in the 1830’s, some still in use by the CSX Railroad. About 2 miles each way. Take 20 east about 18 miles to the village Chester. Go left on Middlefield Rd. & watch for a kiosk on the left showing the trail in less than 2 miles. (Chester & Middlefield)

• Tyringham Cobble- Hike about 2 ½ miles on a loop through farm fields & up a small hill for a charming view of the valley. Includes about 1 mile on the famed Appalachian Trail, which is blazed white. Side trail is blazed blue. Hike the circle going clockwise. Take 20 east to 102 west to a left on Tyringham Rd. Continue 4 miles to the little town of Tyringham. Turn right on Jerusalem Rd. & find a grassy parking area a short distance up the hill on the right. (Tyringham)


• Monument Mountain- Hike 3 ½ mile loop to spectacular views of the Housatonic Valley, The Catskills & Mount Greylock. Strenuous hiking. Steep drop-offs. Not recommended for small children or pets. Take 20 east to 102 west 4 miles to 7 south. Parking on Route 7 about 2 ½ miles south of Stockbridge center. (Great Barrington)

• A-T to Goose Pond- Hike a 3-mile round trip to a shelter on the famed Appalachian Trail at lovely Goose Pond. Woodland hiking. Take 20 east about 5 miles to an A-T, parking area & go south following the white blazed on A-T, passing Greenwater Pond, crossing the Mass. Turnpike on footbridges & up a fairly steep hill to the shelter. About 1 ½ miles each way. (Becket & Lee)

• A-T Mount Everett- Hike to the top of 2600+foot high hill, the highest in Southwestern Massachusetts. Intersect the A-T & hike to the summit with views of New York &
Connecticut. Take 20 east to 102 west & reach Route 7 in Stockbridge. Continue 8 miles through Great Barrington & turn right on 23 west & go about 3 miles to South Egremont. Just past the village, turn left on Route 41, then right on Mount Washington Rd. which becomes East Rd. in the town of Mount Washington. About 7 miles from South Egremont you will find a parking area on your left with a sign for Mount Everett State Reservation. Hike up the fire tower road to the white blazed A-T & turn right up the hill to the summit. The hike is about 2 miles each direction. (Mount Washington & Sheffield)