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Berkshire Hikes

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Colin suggests his top picks for hiking in Berkshire County

There are so many great places to hike in Berkshire county, it can be a little overwhelming for newcomers to the area to pick a spot. The appeal of the county’s namesake – the Berkshire Mountains – is undeniable, which can mean that sometimes the smaller, shorter hikes might get overlooked. Maybe you’re looking just for a relaxing stroll through the woods without the steep hills you’d find at Greylock or Monument Mountain. Or maybe you’ve got a big group and you’d like a walk with wide paths so nobody has to shout to have a conversation. Or you want to have a picnic in a scenic spot but don’t want to lug around the supplies for half an hour each way.

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Kennedy Park is the place to go if you’re looking for a hike through the famous Berkshire woods but you don’t want to spend half the day doing it. The great thing about the park is how well-maintained and laid-out it is. There are trail maintenance teams that go out year-round, so it’s only closed in the most extreme snow. You can pick up a trail map over at the nearby Arcadian shop or pull up a PDF map from here. The nice thing is that the park isn’t that big and there are a lot of trails in it, so rather than having to turn around and walk back the same way when it’s time to head back, you can almost always find a different route that will circle around back to where you began.

Two of my favorite areas are easily accessible from Rt. 7 or 7A. The first, on 7A, is the scenic picnic area shown at the bottom left of the map, which you can access by parking at the white church on the hill (except Sunday mornings) and walking up the access road right next to it (people do sometimes drive up this road, but space is limited and it’s technically for park staff). Once you get to the chain gate, step through and head up the hill to your left. It’s a little bit of a climb, but five or ten minutes later you’ll be at the picnic area with tables, a fire pit, and a lovely overlook where you can get a bird’s eye view of the western Lenox hills and attractions like Tanglewood and Kripalu.

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The second route is much more of a relaxed, shady stroll. Best place to park is at the Arcadian Shop (stop in while you’re there!) where the trail begins right from the parking lot. If you’re looking at the map, I recommend taking the #11 trail in to the #1 trail, and then back up on the #6 & #5 trails to the #11 trail again, but you’re free to make your own route! The icons on the map indicate the steepness of the trails so use those to plan a relaxed or a challenging walk to your liking.

The Arcadian Shop is located at 91 Pittsfield Rd. (aka Route 7/20), and the Church on the Hill is located at 55 Main St. in Lenox, MA. Enjoy your trek through this lovely park!

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