Our Favorite Day Hikes in Great Barrington, Massachusetts

We can’t think of too many better ways to spend a day than hiking through nature. With so much beautiful scenery here in the Berkshires, you’re sure to find all kinds of great places to hike near our Elsewhere in the Berkshires property, plus even more in the surrounding area that would be well worth the drive. Here are a few of our favorite day hikes right here in Great Barrington, Massachusetts.

Lookout Trail in Beartown State Forest

Visiting Beartown State Forest is a great plan whether you’re looking for a day hike or not. The 12,000-acre forest offers all kinds of activities, from swimming to fishing to boating in the summer, to cross-country skiing and snowmobiling in the winter. If you’re heading to Beartown State Forest with hiking in mind, you’re likely intending to walk the Benedict Pond loop, which is another excellent day hike we recommend. But we prefer the oft-overlooked Lookout Trail, a short and sweet half-mile trail that will take you to a peak overlooking the beautiful Berkshires scenery, including some stunning views of the Catskills and Taconic.

The Appalachian Trail

Naturally, we were going to mention the Appalachian Trail. This massive hiking trail spans more than 2,000 miles through the Appalachians, from Maine all the way down to Georgia. This includes a long span through the Berkshires, even passing right through Great Barrington. Our two favorite day hikes on the Appalachian Trail here in GB include Ice Gulch and East Mountain. The Ice Gulch trail features some pretty steep stretches along its 2.2-mile length, but the breathtaking view of the gulch itself, littered with massive boulders and emitting a cool breeze from its seemingly bottomless depths, are well worth the moderate difficulty. The East Mountain trail stretches for 2.8 miles and has a similar difficulty with a relatively steep climb, but it offers incredible views from its namesake ridge. Both of these trails are there-and-back hikes, which is factored into the distances.

Hopefully, these four day hikes at these two incredible locations will give you plenty of ideas for how to spend some of your time at Elsewhere in the Berkshires. If you have any questions about our property in the area, don’t hesitate to reach out!