The Trustees of Reservations Flag Rock WCE
Grove Street, Great Barrington, MA

  • Free
  • Near Public Transit
  • Trailhead
Safety Tips
Flag Rock WCE in Great Barrington, MA | Berkshires Outside
Flag Rock WCE in Great Barrington, MA | Berkshires Outside
Flag Rock WCE in Great Barrington, MA | Berkshires Outside
  • Public Land
  • Private Land
  • Bus Route
  • Trail
  • Major Trail

About Flag Rock WCE

Flag Rock is a stunning lookout spot within the Monument Mountain Reservation in Great Barrington, MA. The lookout spot gives a fantastic view of the valley below and mountains in the distance from a large rock face that is flat and comfortable to sit on and enjoy the scenery and breeze of the mountaintop. It can be accessed from several locations around the reservation, but the Willows Trail is the best hiking trail. The Grove Street trailhead is a shorter, more direct route to the lookout spot, and the Park Street trailhead is a longer trail that travels through the beautiful forests of the Monument Mountain Reservation as it reaches the lookout. It 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 trail. 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. The Flag Rock WCE is perfect for family-friendly outdoor activities due to its easy accessibility and beautiful scenery.


Grove Street, Great Barrington, MA

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Clubs, Retail & Rentals

Looking to meet up with others for team sports or group activities? Check out our list of clubs and leagues in the Berkshires. We also link to an array of outdoor recreation resources: retail shops for gear, rental facilities for equipment, and guides to get you where you want to go! Our list of summer camps will help you plan an overnight or day camp adventure for your young ones.