Hickey and Squaw Loop

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, ...

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...

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 Benedict Pond ("Daily Parking Fee: $8 MA Vehicle, $10 non-MA Vehicle") where you can follow the road to t...

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 make sure to plan way ahead! Each site has a fire pit with grill and a picnic table surrounded by f...

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

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 signs. This pond is popular for people during the day to come hiking, swimming, fishing, and picnic. It ...