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

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.

Map

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

Trails

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.

The Dark Side in Great Barrington

Intro | Parking | Map| Trails | Current Issues

The Dark Side is, in many ways, the antithesis to Reservoir Rocks. It spreads through an older, shadier part of the forest and the boulders here are less trafficked, harder to get to, and spread out. Already grabbing your shoes and chalk, right? Yet for the enthusiastic climber willing to hike a little, some of the best boulder problems in Great Barrington can be found here. From technical moderates (V3-V5) in different styles, to an established V13 waiting for the first ascent of its sit start, or a seemingly endless supply of projects; the Dark Side will keep many climbers busy for seasons to come.

Parking

Currently parking for the Dark Side is granted through a memorandum of understanding between climbers and the South Berkshire Friends Meeting. The large parking lot is on 280 State Road, and they have requested that any climbers using it send them an email at: info@southberkshirefriends.org letting them know that you will be parking there to climb. Please note the Southern Berkshire Friends hold meetings on Sundays from 10:30-11:30am.

Map

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

Trails

The current access to the Dark Side is provided through a rough ‘climbers’ trail’ that runs about half a mile southeast from the South Berkshire Friends property to the Whale boulder. Heading from the parking lot towards the forest, you will walk through a marshy area with reeds and quickly bear left. Continue through the thicket and then duck under a bending tree to gain access to the forest. Once in the forest travel southeast towards the pin for the whale. You will travel uphill gradually, and after about 0.5 miles will start seeing boulders, the Whale being the biggest one around. The Whale has problems like Nostalgia V10, a sloper traverse on the far right of the block, or Tim’s Problem, a dynamic V5 on small holds. There is also a warm up traverse V3 climbing right using the slots to the left of Nostalgia. If you walk climbers left of the whale and around the hill is the Darkside Arete V13 and Moondance V8. Climbers right of the whale will take you to Commissioner of Adultery V5 and the Elyse Problem V6. Continue exploring to find some of the different projects waiting for a little wire brushing!

Current Issues

While the majority of boulders at the Dark Side are on East Mountain State Forest, this property abuts that of other landowners, including that of the generous South Berkshire Friends. Both with the approach and where you explore, please be respectful as you appreciate the excellent climbing.