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Yankee Inn
461 Pittsfield Rd. Routes 7/20
Lenox, Massachusetts, 01240, United States
413-499-3700

Hiking in the Beautiful Berkshire Hills

  • Valley River
  • Monument Mt Sunset

The Perfect Hike for Every Guest, by Danielle Goulet

  • Mt Greylock

There are so many breath-taking sights to see while staying in Lenox at The Yankee Inn, and there is no better way to experience the beauty of nature this summer than hiking! There are hundreds of beautiful hiking trails here in the Berkshire Hills, but I have listed some of my absolute favorites to help you choose the right place for you. Whether you desire to climb to the summit of a mountain, experience the historical thrills of the past, or hike to a picturesque waterfall, we’ve got you covered! During my most recent hike, this spring, at Sheep Hill Rural Lands Foundation, in Williamstown, MA, I actually experienced a little bit of everything, followed by a delicious lunch at the nearby 6 House Pub. All of the pictures shown on this page were actually taken by me, during various hikes, specifically, Bash Bish Falls, Monument Mountain, and Sheep Hill. Each place offers guests a unique and unforgettable experience of the beautiful Berkshires.

The first hike which I absolutely loved, here in the Berkshires, is Bash Bish falls which is pictured above. The trail starting from the New York side, which is closest to us here at The Yankee Inn, is very easy to navigate, and the scenery is exquisite! Once you arrive at the falls and small swimming hole, there are many perfect photo opportunities, or for the more adventurous spirit, you are able to climb the trail above the falls for an amazing view of the entire valley and hills. The trailhead for Bash Bish falls is located in Copake Falls, NY a short just a short distance from Lenox. This hike is perfect for our guests with young children, as the trail to the falls is quite short and the terrain is flat. There is also a nearby park with picnic tables, and a grilling area to make a perfect lunch spot.

  • bash bish
  • bishbash_main

The next hike which was certainly a favorite of mine was Monument Mountain, which is only a 15-20 minute drive from The Yankee Inn, located in Stockbridge, MA. Monument Mountain is the perfect challenge for hikers of every level, from beginner to novice. The mountain has two designated trails which both lead to its summit. The trail on the left side of the mountain is an easier ascend, and terrain is considerably flat, with a very slight incline. The trip to the summit and back down takes approximately 5-6 hours, and is perfect for children as well. The trail on the right side of the entrance is considerably steeper in certain parts, but is also a shorter trip to the top, with better views, in my opinion. Hikers can also see the infamous devil’s pulpit (pictured below), which is a giant rock formation in the center of a nearby valley. Brave adventurers each year attempted to scale this rock formation, and it is definitely worth seeing!

Finally, the most recent hiking destination which I visited was Sheep Hill, which is owned by the Williamstown Land Trust Foundation. Sheep Hill is a perfect spring hike destination because the land dries up from the melted snow quite fast. Near the parking area, visitors can observe the historical dairy barn which has been renovated and restored, a small pond, and the trailhead which displays a map of all the various hiking, snowmobile, and skiing trails on the land. The first sections of the trails spreads across the vast, grassy fields, with spots along the incline to stop for photo opportunities or a quick rest on provided benches. When hikers arrive at the top of the fields there is a panoramic view of the Berkshire mountains including the highest peak in Massachusetts, Mount Greylock. At the top of the fields is a dirt road, and if you cross over into the wooded area, you will discover various hiking trails and a map for connecting ones. I hiked the Fitch trail, which consists of a 5 mile loop, steep in some areas, but beautiful views including a small stream which the trail runs beside in some parts.

  • bishbash_main