Great Barrington, Massachusetts
Monument Mountain Loop
A short, dramatic Berkshires loop to white quartzite cliffs and Squaw Peak.
- Difficulty
- Moderate
- Length
- 2.6 mi
- Elevation Gain
- 720 ft
- Duration
- 1.5–2.5
- Best Season
- Apr–Nov
- Permit
- Not required
- Dogs
- Allowed
- Features
- Quartzite cliffs, Berkshires views
About the trail
Monument Mountain is a Trustees of Reservations property famous for its white quartzite ledges and a literary footnote — Herman Melville and Nathaniel Hawthorne first met on a hike here in 1850. The Hickey Trail climbs to the open cliffs of Squaw Peak (1,642 ft) with sweeping views east across the Housatonic Valley to October Mountain. Descend the easier Indian Monument Trail for a loop.
Trailhead map & directions
Trailhead: 42.2376, -73.3531Get directions →
Turn-by-turn route
- From Great Barrington, drive 3 miles north on US-7.
- Park at the Monument Mountain Reservation lot on the west side of the highway.
- Take the Hickey Trail (blue blazes) up to Squaw Peak.
- Descend via the Indian Monument Trail (white blazes).
- Return to the parking lot.
Parking
Trustees lot off US-7. $5 suggested donation for non-members.
Tips from the trail
- Cliff edges are unfenced — keep kids and dogs close.
- Spectacular at peak foliage in early October.
- Combine with lunch in Great Barrington or Stockbridge.