Flag Rock

This moderate route to Flag Rock begins at a roadside pull-off on Route 183 in Great Barrington, just beyond Taft Farm. From the trailhead, follow Willow’s Trail as it climbs steadily through mixed forest, weaving past rock outcrops and occasional ledges. At the junction with the Cross Over Trail, stay on Willow’s Trail and continue uphill. The final stretch becomes steeper, with sections of uneven footing and short rocky scrambles. After cresting the ridge, the trail leads directly to Flag Rock, a broad, open ledge with sweeping views across the Housatonic River Valley. On clear days, hikers can spot the Taconic Range and even the distant Catskills. Follow the same path to return to the trailhead and complete the route. This route stays within Monument Mountain Reservation, managed by The Trustees of Reservations, but passes close to private property near Flag Rock. While well-marked, some connecting trails in the area may be less maintained—remain on the main trail and respect property boundaries near the summit. Flag Rock is accessible year-round, with winter snowshoeing possible depending on conditions. The open ledge provides a rewarding destination and a classic example of day hikes in the Berkshires with standout valley views.