Great Barrington

Flag Rock is an out-and-back trail that provides a good opportunity to view wildlife located near Great Barrington, Massachusetts.

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

East Mountain via Appalachian Trail is an out-and-back trail where you may see beautiful wildflowers located near Great Barrington, Massachusetts.

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

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