So in our quest to get out every weekend, last weekend I decided that we should head down to the southern Berkshires. We’re in Williamstown every day of our lives it seems, but it had been years since I had been down to Lenox and Stockbridge. Literally years, when I lived in NYC we went to Tanglewood and Jacob’s Pillow one weekend and it lives on as a truly wonderful (and expensive lol!) memory. I had never even heard of Great Barrington, but some friends here recommended it, so we started there. We did not take scenic Route 7 but instead weaved over to the NY State Thruway, it’s faster but not as picturesque from Vermont.

Great Barrington was okay, apparently it’s really known for restaurants, we were not hungry but we did stop at Patisserie Lenox (which also has locations in Hudson NY and Northampton) for a coffee and pastry. It was cute, nice, a traditional patisserie. But if it were me, I’d do my research on restaurants before I hit Great Barrington and definitely eat there. It’s not super picturesque at all, but it has decent shopping too, you could easily while away a few hours there.

By far my favorite town of the 3 is Stockbridge. The centerpiece of Stockbridge is the Red Lion Inn, a very famous and classic inn that is absolutely New England gorgeous. We didn’t eat there or stay of course, but we did go inside and explore, I’m posting a few photos of the interior below. I’m definitely going to go back for lunch or dinner, and they have live music in their little pub at the weekends.

There are lots of good photo opportunities in Stockbridge, it’s a super cute little town. It was hard even on a gray Saturday to get a shot with no people in it however,

Lenox is a lot less picturesque and I didn’t even take any photos there, because there just wasn’t anything very charming or New England-y, but if you want to shop and eat, especially in summer, Lenox is the place. There are lots of high-end stores there (I mean, Berkshires high-end there’s not like a Gucci lol) but it’s good shopping and dining, a lot of New Yorkers come to Lenox for the summer Tanglewood and Jacob’s Pillow season so it definitely caters to that crowd and isn’t like, a sleepy New England town.

Overall I just don’t love the Berkshires like I love Vermont, it’s so weird once you cross the state line it’s a whole different vibe, Vermonters are more like Southerners, very friendly, not terribly sophisticated (in a good way) and definitely not cosmopolitan, and the Berkshires definitely has more of a Boston suburbs vibe (think crunchy ladies in $500 vegan leather jackets driving Priuses lol). I just love all of the different aspects of New England and I feel lucky the Berkshires are so close!