Headed over to the southern Berkshires after work today to hike 1454 foot Flag Rock on yet another hot and humid afternoon. Flag Rock is part of the Trustees of Reservations Monument Mountain Reservation in the town of Great Barrington, and is located in the NW corner of the 555 acre property.
It has been several years since my last visit here and I was quite surprised by the progress done on a small parking area, trail signage, and even trail blazes. My previous visit, back in 2016, I had to park on the shoulder of the road in a grassy field before hiking the unmarked herd path to the top. Today, there is an actual parking area on the east side of Route 183(just north of Ramsdell Road) with orange trail blazing heading into the woods, as well as a trail map.
From the parking area(Elevation 738 feet)I headed east on the orange blazes of Willow's Trail, gaining elevation on a wide old woods road with just a bit of mud underfoot.
A short distance in, the trail turns sharply left(north), soon passing by a purple marked Crossover Trail on the right. Continuing past the junction, the trail continues to makes its way north, gaining elevation slowly but surely. Although the ascent is barely noticeable much of the time, the humidity had me perspiring quite a bit though.
The trail basically continues straight, going through a high pass, with steep, rocky slopes rising high above on both sides. After about 1.8 miles, and one last steep push up, the trail arrives at the clearing atop Flag Rock. From here, there are good views west directly over the community of Housatonic down below through the haze. Unfortunately, as evidenced in this photo, heavy rain was just about to move through.
The peak's namesake-Flag and Rock-with clearer skies further to the north just beyond Tom Ball Mountain's ridge.
On the southwest horizon, the southern Taconic ridgeline forms quite a formidable backdrop.
After a few moments up at the top, the front got a little too close for comfort, so I quickly headed back down, passing beneath the large cliff bands just below Flag Rock. With the winds picking up and dark skies above, I moved swiftly down, hoping to beat the rain.
Sadly, my attempts to beat the rain failed, as a torrential rainstorm caught up with me, drenching me in just a few minutes time. I arrived back at the car soaked, but actually feeling a bit refreshed. 3.7 miles RT, with just under 800 feet of climbing for the day.
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