Hike Flag Rock in Great Barrington, MA; Trail Guide

view on top of flag rock in massachusetts with view of green trees and some yellow leaves at end of summer

If you’re looking for a super scenic hike WITH VIEWS in Great Barrington that’s NOT busy and popular then look no further than Flag Rock! Flag Rock is the much quieter western side of the 555-acre Monument Mountain Reservation.

You’ve likely seen the main entrance for Monument Mountain on Route 7 – it’s a huge lot that’s usually crowded and full on weekends. You can still hike and take advantage of all the beauty here, but on the less popular trail going up to Flag Rock – a secret (or lesser known) lookout and hike in Great Barrington.

I lived in Great Barrington for several years and it wasn’t until I was living back in Connecticut that I discovered this hike! Go figure… 😉 But it’s a testament to it being a hidden gem with most people flocking to the other side of Monument Mountain to go up the Hickey and Peeskawso Trail (that’s a mouthful!).

I couldn’t believe how nice this trail was. It’s mostly a wide path through the woods with signs along the way, which makes it very easy to follow even if you’re normally not great with trail directions.

This guide will tell you everything you need to know to hike Flag Rock – where to park, what the trail is like, and even turn-by-turn trail directions so you can’t get lost! ☺️

Flag Rock is located within the 555-acre Monument Mountain Reservation managed by The Trustees of Massachusetts; the nation’s first and Massachusetts’ largest preservation and conservation nonprofit.

Located in the quaint Berkshire town of Great Barrington, Massachusetts, founded in 1761, and known as the birthplace of civil rights leader W.E.B. Du Bois, it has long been a hub for progressive thought and action. There is so much to do in Great Barrington from its cultural and art options to numerous renowned cafes and restaurants to hiking trails like this one up Flag Rock.

Table of Contents

🥾Let’s hike Flag Rock! Trail Guide Below ⬇️

Hike the well-marked and easy to follow Willow’s Trail to the top of Flag Rock with wide open views facing west toward the Catskills.

Flag Rock Trail Overview📍

Miles: 3.83 miles
Elevation: 797 ft elevation gain
Level: Moderate
Trail Type: Out & back
Average Time: 1 hour 45 minutes
Parking: Navigate here: 42.23638, -73.34816, a small pull off for a few cars on Park St
Dog-friendly: yes 🐶
Trail Highlights: easy-to-follow trail and western facing views over Housatonic River Valley

Find the trailhead: From Mason Library at 231 Main Street in Great Barrington, turn right (head north) on Main Street (Rt 7). After 0.4 miles turn right onto State Road (US-7). After 1.9 miles, turn left onto Old Stockbridge Rd (RT-183). After 0.5 miles on Old Stockbridge Rd, stay straight as it becomes Park St N (RT-183). After 1 mile you will see a small pull off with room for a few cars and a trailhead sign on the right side of the road.

Starting from a small parking area on Route 183 (Park Street N) on the western side of Monument Mountain, you’ll pick up the orange blazed Willow’s Trail which winds through diverse ecosystems. You’ll hike through evergreen spruce and pine forests to deciduous trees like oak and maple, with vibrant underbrush of mountain laurels, hobblebush, and ferns.

You’ll walk about 1.9 miles with a gradual incline along Willow’s Trail, staying left the whole time on orange, until you come to an impressive overlook with an American flag set atop a rocky outcrop. This highlight offers hikers and hounds breathtaking westerly and southerly views of the Housatonic River Valley and the surrounding Berkshires.

🗺️ TURN-BY-TURN TRAIL DIRECTIONS 🧭

1.) From the top left corner of the parking lot, find the trailhead with a map along with several signs welcoming you to Monument Mountain, where you will start on the wide dirt path along the orange blazed trail. 🧡