Leaf-Peeping Season in the Berkshires

The majority of us here at the goop offices in Los Angeles are not actually from Los Angeles. We come from all over—the North, South, East, and Midwest. And for most, it didn’t take much more than a few mid-November beach days to outweigh whatever nostalgia we felt for season-appropriateness. Our most recent transplant, editor in chief Danielle Pergament, and her love for a small town in Massachusetts, jogged our memory.

I just became a fall person. I’m an East Coaster, and to be honest, the charm of foliage was always if not lost, a little misplaced on me. Don’t get me wrong—crimson oak trees are certainly beautiful. But all those crunching leaves and scratchy sweaters also came with a silent message: The beach is closed, school is starting, and grey slush season is not far away. But a few weeks ago, I became a fall foliage proselytizer. See, my family and I just moved to Los Angeles—we are now people who bodysurf in the Pacific Ocean before dinner and can lay claim to a palm tree. I’m hardly complaining, but in leaving the East Coast, we also left a lovely, lopsided cabin in Monterey, Massachusetts, in the heart (or just south of the heart) of the Berkshires.

I haven’t laid eyes on the place in months, but I can guarantee that the porcupine is still sleeping in the apple tree, the creek is still populated with my daughter’s fairy houses, the bear still ambles by at dusk—and the leaves are a riot of blazing colors.

As much as I miss a proper fall, I also miss the food, the hiking, and the shopping (which sounds weird coming from someone who lived in New York and now lives in Los Angles, but: trust). There’s something about the Berkshires that attracts people with great taste; a cool, bohemian bent; and world-class culinary skills. (Dan Barber’s farm, Blue Hill—as in the Blue Hill restaurants—is here.)

It’s about two and a half hours from New York City, and the drive gets prettier and prettier as you head north. When the roads get smaller and less paved, just beware of the wildlife. And if you see a huge, shaggy brown dog trot into the woods, well, chances are it isn’t a dog.

Danielle’s Picks

  • Blantyre


    I haven’t been (yet) because it just reopened a few months ago, but this Relais & Château hotel in Lenox looks like a New England Hogwarts—with towers and spires and a beautiful, creepy-cool vibe. It has a world-class restaurant, an in-house spa, acres of rolling hills, a cottage designed by Serena & Lily, and BMWs on loan if you want to cruise around and check out the foliage. It also has something called a Champagne Salon, which sounds like a glorious place I plan to visit very soon.

  • Butternut Ski Resort

    Butternut Ski Resort

    As its name would suggest, Butternut is adorable. In the winter, it’s the place for skiing, tubing, snowboarding, and hot chocolate. But this time of year, Butternut runs the chairlifts as a sort of aerial tour of the foliage. Granted, if you’re in the Berkshires in September, you can’t not see the changing leaves, but this view is next-level.

  • Cantina 229

    Cantina 229

    Josh and Emily Irwin own one of those farms that make you think for a hot second that you could maybe be a farmer: the meadows and the free-roaming chickens and the views and the quiet beauty of the place. Josh runs the kitchen, and everything that comes out of it is amazing. The menu has an unexpected international flair, and it changes all the time. The bibimbap is a mainstay probably because it’s ridiculously good. The bartenders are no slouches either—drinks are potent and expertly made. If your weekend turns into a week, go on Tuesday—Taco Tuesday is a foolproof crowd-pleaser.

  • Hike


    There are amazing hikes all over the place in the Berkshires. My favorite is Bartholomew’s Cobble—the slope is gentle enough that my kids don’t burn out. But once you get to the top, it’s just magic. My daughter says it looks like The Sound of Music. And granted, the Berkshires may not have the altitude of the Austrian Alps, but the beauty—especially when it’s delivered in so many vibrant colors—is intoxicating.

  • Rubiner's Cheesemongers & Grocers

    Rubiner's Cheesemongers & Grocers

    I am such a regular at this cheese shop that Matthew Rubiner, the owner, has become a great friend. He is a man with an encyclopedic knowledge of cheese and impeccable taste. The shop is in the old bank right on Main Street in Great Barrington and is as charming and grand as an old bank with giant pillars can be. If a cheese store can have gravitas, this one does. I can’t get into the selection of cheeses because this post will turn into a book, but I will say this: Get the Robiola di bufala and the Mühlistein. Also the Dutch Wilde Weide. They will ruin all others for you. Beyond a world-class selection of cheese, Rubiner’s also sells the crackers, olives, nuts, cured meats, caviar, chocolates, and everything else you would possibly need to create the world’s most enjoyable hors d’oeuvres.

  • Rubi's Coffee & Sandwiches

    Rubi's Coffee & Sandwiches

    Just behind Rubiner’s is its café. Tucked into a charming brick alley, Rubi’s offers 175,423 kinds of grilled cheese sandwiches—including a fried egg grilled cheese in which the yolk miraculously doesn’t harden and somehow spills out over the gooey Compté and crusty bread and the whole thing will make you see God. It’s not possible to have a bite of food here that’s short of outstanding.

  • The Great Barrington Farmers' Market

    The Great Barrington Farmers' Market

    The local farmers’ market runs every Saturday from 9 a.m. to 1 p.m. from May through October. This is not only the place for hay rides, freshly baked bread, bright vegetables from Farm Girl Farm, and grilled sausage from North Plain Farm—it’s also the social event of the week. Plan to hang out for a while, get some stuff for dinner, and stay for lunch: There are tables set up for the occasion.

  • The Inn at Kenmore Hall

    The Inn at Kenmore Hall

    Scott Cole used to run the Monterey General Store, and everything in the shop was simple, curated, and beautiful. It was more like the home of the world’s chicest farmer than a general store. Just over a year ago, Cole and his partner, Frank Muytjens, formerly the head of menswear at J.Crew, bought an old home (as in 1792) and poured love, sweat, and Farrow & Ball paint into the project. It is now the Inn at Kenmore Hall—five rooms and a carriage house that have been redone as only two people with exquisite taste could do. Every last detail is comfortable and elegant, the proprietors are friendly and delightful, and the meadows around the inn are so vast and majestic, they can only be called grounds. You’ll never want to leave.

  • The Prairie Whale

    The Prairie Whale

    Mark Firth started Diner and Marlow & Sons in Brooklyn before packing up and opening a farm-to-table restaurant in the Berkshires. The place is fun and lively and reliably packed. Go early and have a drink at the bar—it’s a great scene.

  • Twigs


    I can’t go into this store without buying something—No. 6 clogs, a breezy Ulla Johnson dress, great Nili Lotan cargo pants. You’d never expect such a cool, well-curated store to be in the middle of farm country, but the vibe of the place is completely in keeping with the Berkshires: arty, creative, easygoing, and so pretty. If I time my visit right, afterward I go a few doors down to Allium for a Negroni and a kale salad or Botanica for a Mi Corazón, a smoky tequila drink.

  • Miraval Berkshires

    Miraval Berkshires

    Miraval’s newest property—a centuries-old Tudor-style mansion—is set on 380 acres, with plenty of room for the adventurous to roam and the exhausted to relax (the resort takes its device-free policy seriously, so it’s the perfect place for a digital detox). Hike or bike the secluded trails, explore Laurel Lake by paddleboard or kayak, hit the challenge course for some hatchet throwing (really), or take in a yoga or Pilates class. The spa menu changes with the seasons, but Ayurvedic treatments are always on, along with unique offerings like the guest-favorite kombucha facial. Mix in a beekeeping class, a trip to the equine center, and consciously cooked, complimentary meals and you’ll find that the perfect adult summer camp does exist.