The Best Hiking in 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 ...

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

Appalachian Trail: Monterey to Sheffield is a point-to-point trail where you may see beautiful wildflowers located near Sheffield, Massachusetts.

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

On a spontaneous adventure, we were lucky to have ended up car camping at the beautiful Beartown State Forest. From the main entrance of the state forest, the campsite is only a few minutes drive to the right of the road. The campsite is popular, but only limited to 12 sites, so during the summer...

If you ever decide to go to the beautiful Beartown State Forest, be sure to enjoy the short but worthy hike to the vista on the Lookout Trail for views that stretches out to the mountains. There are two places to park:  1. From the main entrance of the park, you can get a spot at the lot at Bened...

This is no ordinary loop, it's rain forest-like feels with small hills and curves, wooden bridges over marsh, and lookouts over the pond will keep you in awe at every corner! The trail is easy to find and easy to follow. When you park at the boat launch area, follow the blue blazes and trail sign...

Appalachian Trail from Jug End to Bear Mountain is a point-to-point trail that takes you by a lake located near Great Barrington, Massachusetts.

Jug End Road is a loop trail that takes you past scenic surroundings located near South Egremont, Massachusetts.

Alford Springs Reservation is a loop trail that takes you through a nice forest located near Great Barrington, Massachusetts.

Turkey and Airplane Trail is an out-and-back trail where you may see beautiful wildflowers located near Great Barrington, Massachusetts.