Trail of the Ledges and Overbrook Trail

You will park at the end of Park Street in Stockbridge, Massachusetts.  From the parking are you will cross a beautiful bridge over the Housatonic River.  The trail crosses railroad tracks and immediately begins to climb into the woods.  You will reach a split in the trail, a left will take you steeply up the slopes of the hillside.  After less than a mile of climbing, you will see the 30 foo...

At 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under 3 miles round trip.Personally, I chose to take the Hickey Trail for the bulk of the elevation gain, ...

Mt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.

Kinderhook Creek is a loop trail that takes you by a river located near Stephentown, New York.

When you reach the falls, you can cliff jump into a large swimming hole at the base. The best time to visit the falls is from April to November. Please note that dogs are not permitted here. Parking is at a cemetery, and the gates are open from 8am to 9pm. Use common sense before cliff jumping - check your route and ensure it is clear of rocks!

Park at the Junction of Sperry Rd and Rockwell Rd. To get to the trailhead, hike along Sperry Road for about 30 minutes. (Not to the end of the road, see map below.) Then hike along the March Cataract Trail, an out-and-back. You can bring dogs on leash. The trail is short but steep in some parts also the trail is accessible March-October. Enjoy the wildflowers, wildlife, and waterfall on this p...