A large boulder covered in snow.

Flag Rock in Great Barrington

Intro | Parking | Map| Trails | Current Issues

Flag Rock is a satellite climbing area in Great Barrington with about a dozen established boulder problems and good potential for further development. The climbs here range from tall moderates to classic harder lines featuring small holds and powerful movement. The approach is shared by a popular hiking trail on the back side of Monument Mountain that leads to a scenic overlook. While not as developed or concentrated as other areas in Great Barrington, and protected by an approximately 1.5 mile mostly flat approach, the high quality of the climbing and potential of the area merit a visit.


Parking for Flag Rock is the roadside pull-off on the side of Route 183 in Great Barrington. Coming from the south (from the town Great Barrington) the trailhead is on the right 0.2 miles after Taft Farms. If traveling from the north from the town of Housatonic, the trailhead is 0.3 miles on the left after the Paper Mill. The parking lot is open year round and many hikers also enjoy the area.


Click here for a link to the interactive map above of all the Western Mass crags discussed on this site.


After parking in the lot on Route 183, begin hiking on the Willow’s Trail. There is an uphill section at the beginning of the trail but after a bit it levels off. There are multiple forks in the well maintained hiking trail, keep left at all of them. After about a mile and a half the trail opens up and you will start seeing boulders on both sides. Some of the initial climbs are moderate, including a highball V1 crack on the right side of the trail, with a shorter V4 problem on the left side of the same boulder. Keep following the trail north and you will come to the Jason Goes Rafting boulder, the prize of Flag Rock that has been decorated by some local ‘artists’. Paul Robinson got the first ascent of the overhanging crimp line in 2004, which gets between V8-V10 depending on who you ask. There are more moderate highballs on either side of the boulder and a great deal of potential for first ascents around. Bring all the pads you can muster, preferably by way of good friends!

Current Issues

Flag Rock is currently open to climbing without access issues. Please help to keep it this way by parking responsibly, keeping noise down, brushing ticks/chalk, respecting other land users, and leaving no trace.

Western Mass Bouldering History: A film presentation on the past, present, and future of New England’s best bouldering

Western Mass Bouldering History: A film presentation on the past, present, and future of New England’s best bouldering

A presentation by Jonah Meyer and Kai Webler.

Watch archival footage of historic first ascents, learn more about the development of bouldering in Western Mass, and watch high-end video of modern first ascents.

Tuesday, February 26th
7:00-9:00 Central Rock Gym Hadley, Party Room


” Western Mass Bouldering History” is one of two Winter Seminars hosted by the Western Mass Climber’s Coalition this year. Seminars are free and everyone is invited to participate.