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You’ve seen the vista from Olivia’s Overlook, but did you know that it’s also the trailhead for more than 6 miles of hiking trail? From here you can access: Walsh (easy access), Charcoal, and Burbank Trails. Those trails connect to Brothers Trail, lead you to Monks Pond, or are very near to Jackson Pond’s boardwalk.

Since its construction, the Brecher boardwalk has tempted trespassers eager to see where it leads. The answer: stunning views of Jackson Pond.

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Yokun Ridge : 42.350966, -73.334756


Yokun Ridge North Trail Map & Guide

Yokun Ridge South Trail Map & Guide

Yokun Ridge Topo Map

Yokun Ridge Aerial Photo Note: this map describes the new Brothers Trail

Charcoal Trail: 1.6 miles roundtrip, 1 hour, moderate

Brothers Trail: 0.9 miles, 0.75 hours, one-way, easy

Burbank Trail: 3.2 miles roundtrip, 2 hours, moderate

Special features: Great views, Monks Pond, Jackson Pond boardwalk



Yokun Ridge is best accessed from Olivia’s Overlook.

From the center of Lenox (Routes 7A and 183): Take Route 183 west for 1.5 miles, passing Tanglewood. When Route 183 curves left, bear right onto Richmond Mountain Road (sign says to Rt. 41/Richmond). Drive 1.5 miles and the parking lot will be on your left.

From Pittsfield (intersection of Route 7 (South Street) and Route 20 (West Housatonic Street): Take Rt. 20 west 0.8 miles. Make a left onto Barker Road and drive 6.6 miles. Make a left onto Lenox Road and drive 1.8 miles to Olivia’s Overlook, on the right.

From West Stockbridge at the intersection of Route 102 and Swamp Road (across from Shaker Dam Coffee House & Stanmeyer Gallery): Head north on Swamp Road and make an immediate right onto Lenox Road. At 2.0 miles, turn right and continue another 0.1 mile to Olivia’s Overlook on the right.

42.3519, -73.3377 (Olivia’s Overlook trailhead parking)
42.3543, -73.3292 (Brothers Trail trailhead parking)
42.3427, -73.3319 (Jackson Pond frontage)


CHARCOAL TRAIL: Hang a right at the fork near the kiosk and follow the gentle trail to the rock ledges on West Stockbridge Mountain’s northern summit. Continue the loop by descending the Charcoal Trail, keeping an eye out for the tell-tale circular level areas where wood piles once smoldered. Follow the Brothers Trail toward Shadow Brook, Kripalu and Old Baldhead Road to witness amazing stonework put in place by the trail builders

BROTHERS TRAIL: Access the Brothers Trail starting at the trailhead at the base of Old Baldhead Road, crossing Richmond Mountain Rd and following the staircase down. From here you can enjoy the incredible stonework put in place by the trail builders and do an out and back hike, or experience a loop by connecting to the Charcoal trail then to Olivia’s Overlook and returning back to your car via the Burbank Trail to Monks Pond and following Old Baldhead Road down.

JACKSON POND: A path through the woods leads to a boardwalk with lovely views over Jackson Pond to Yokun Ridge. Birds galore in the intervening woods and wetlands.


At the center of the 734-acre Yokun Ridge Reserve is Olivia’s Overlook.  This popular overlook is also the trailhead for the 6 miles of trail that BNRC maintains on Yokun Ridge.  Trails range from the easy access Walsh Trail (a gradual climb to stunning views all the way to Great Barrington) to the long inter-locking loops of the Burbank and Brothers Trail.  You’d like to spend some time at a quiet pond?  Hike the Burbank Trail down to Monks Pond.  If you’re hiking with a little one, let them explore the pools of Shadow Brook on the Brothers Trail.  If you’re a bird watcher, park at the boat launch on Route 183 and walk over to Jackson Pond where BNRC maintains a boardwalk through the wetland there.

The bulk of the Yokun Ridge Reserve is made up of parcels donated by the Stokes family, the original owners of the Shadowbrook Estate.  Other donations were made by local families who loved these hills just as you do.


1. Alford Springs

2. Hoosac Range

3. Basin Pond

4. Stevens Glen

5. Olivia's Overlook at Yokun Ridge

6. Clam River

7. Hollow Fields

8. Bob’s Way

9. Steadman Pond at Hudson-Howard

10. Housatonic Flats

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