Stockbridge

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...

Mary V. Flynn Trail is an out-and-back trail that takes you by a river located near Stockbridge, Massachusetts.

Bowkers Woods Lower Trail is a loop trail that takes you by a river located near Stockbridge, Massachusetts.

Beartown Mountain to Laura's Tower is an out-and-back trail that provides a good opportunity to view wildlife located near South Lee, Massachusetts.

Hickey, Squaw and Indian Loop is a loop trail that provides a good opportunity to view wildlife located near Great Barrington, Massachusetts.

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, ...

Hickey and Squaw Loop is a loop trail where you may see beautiful wildflowers located near Stockbridge, Massachusetts.

Housie Rail Trail is an out-and-back trail where you may see beautiful wildflowers located near Housatonic, Massachusetts.

Monument Mountain Summit is an out-and-back trail where you may see beautiful wildflowers located near Great Barrington, Massachusetts.