Monument Mountain Reservation The Trustees of Reservations Flag Rock Trailhead

Park Street, Great Barrington, MA

About Flag Rock Trailhead

The Flag Rock Trailhead provides access to an excellent hiking trail, the Willows Trail, which travels through the forests of the Monument Mountain Reservation. It is a beautiful trail of moderate challenge, as it is a steep climb up the mountain in some areas, and it can be rocky. However, the scenery of the trail and the view waiting at the end make it worth the challenge, making this an ideal family-friendly hiking destination in the Berkshires. The path is broad and passes through many diverse ecosystems that will capture the attention of any hiker. Evergreen forests of spruce and pine trees shadow the trail in some parts, and deciduous trees of oak, maple, ash, and other natives of New England create a pleasant atmosphere for the path. A dense underbrush of mountain laurels, hobblebush, and a wide variety of ferns add vibrant color to the forest. The Willows Trail also passes by stunning rock outcrops that engage the imagination. At the end of the trail, the Flag Rock lookout spot gives a spectacular view to any hikers who reach it, looking out over the valley below. 

Lands north of Flag Rock are private property, please do not utilize trails beyond Trustees property.

A large parking area and kiosk with maps and notices about the trail are available and make this an easily accessible trailhead for families and people of all ages. The Willows Trail at the Flag Rock Trailhead is an excellent family-friendly hiking spot in Western Massachusetts and a destination that nobody should miss.