The Insider’s Guide to the Berkshires

Ever wish you could text the most stylish people in the world to ask them for their lists of things to do in the places they know best? Here are insider travel tips for those who would never be caught dead in a tourist trap. Bon voyage!

Who

Everyone knows that the Hudson Valley is all the rage these days, but the region just across the Massachusetts border is no less breathtaking or chic. With its mighty mountains, cotton-ball clouds, and heavy-hitting cultural scene, the Berkshires have far more on offer than one might think. To wit: Not a single expert who spoke with W suggested leaf peeping—though, if you’re inclined to see the area's foliage in its full glory, go in October.

Four taste-making Berkshires residents share advice on how to explore the area known for its big-sky beauty and small-town quirks: Ruth Riechl, an author and former editor of Gourmet magazine; Thando Hadebe, the Art Director of Tory Burch; Frank Muytjens, the former J. Crew menswear designer and co-owner of the Berkshire’s Inn at Kenmore Hall; and Julie Rubiner, the head designer of Eileen Fisher (and wife of Matt Rubiner, the area’s most celebrated cheesemonger).

What

What to Bring

Even if you’re leaf agnostic, you’ll flip for all the other autumnal charms of the Berkshires. With ample mountains to hike and picnic-ready pastures, grippy shoes are in order—for example, Salomons.

Bring a baseball hat to protect your skin from the daytime sun, and pack your favorite fleece or barn jacket for the chill that sets in at cocktail hour.

Fireside reading sessions are key to any Berkshires experience, so don’t forget a good book and a pair of your finest slippers.

What Not to Bring

The Berkshires does chic in its own way. Vintage Saabs outnumber flashy sports cars, Blundstones beat out Manolo Blahniks, and nobody messes with makeup, so leave your red lipstick at home. Reichl describes the local style as “rich hippie,” so pack an Owala water bottle and grab your favorite jeans and a handful of James Perse T-shirts. If you plan to go to Hy's Fried—a new fried chicken restaurant with a DJ booth and epic post-dinner dance parties—that’s your excuse to bring a sparkly dress from Rachel Comey.

What to Keep in Mind

The Berkshires have an enormous footprint, with some 30 towns scattered across 2,000 square miles. Unless you’re staying for months, a successful visit will entail keying in on a few locations. The bustling (for the Berkshires) town of Great Barrington is not to be missed. West Stockbridge has an old-timey New England feel that is best experienced in the lobby of the Red Lion Inn, curled up by the fireplace and nursing a hot toddy.

To fully experience the area’s splendor, leave your pretenses at home. “The thing that amazes me about the Berkshires is the sense of community, even with people I’m meeting for the first time,” says Muytjens, who lives in the Berkshires full-time. “I get coffee at the same cafe every day, and there’s a man I sometimes see at the hardware store across the street. I don’t know his name, but we greet each other every time.”

Where

Where to Stay

Inspired by classic American motels, Tourists, in North Adams, offers yoga, hikes and Pilates.

Wellness hounds also love Miraval, in Lenox, which is known for its exquisite spa and portfolio of swimming pools.

The old-school move is to stay at the Red Lion Inn, a historic Stockbridge mainstay with a charming cellar pub. An intimate option is the Inn at Kenmore Hall, a converted Georgian boarding school that is a small yet smart tribute to good taste.

Where to Eat

If there’s one thing that might connect the elaborate constellation of people and places that comprise the Berkshires, it’s a love of local, fresh food. The grown-up answer to Erewhon, Guido’s is a gourmet supermarket where you might spot Meryl Streep or Morgan Spector. “It’s not pretentious and it’s not crazy expensive,” says Reichl. Another can't-miss foraging spot is Rubiner’s, the iconic wine and cheese shop located in a former bank building on Great Barrington’s main drag. “Matt Rubiner knows more about cheese than anyone I know,” says Reichl. Ruby's—Rubiner's cafe—serves sensational baked goods and grilled cheese sandwiches.

For a fun diner lunch, try Neon Newt, which serves sandwiches that have le tout Berkshires talking. If you fancy a proper sit-down place, head to Heirloom Lodge, in West Stockbridge, where California food legend Matt Strauss makes luxuriously pared-down dishes served under the space’s cathedral-like wooden beams. “Matt ran what was one of my favorite restaurants in Los Angeles before moving to the Berkshires,” says Reichl. “The food is very vegetable-forward, and it’s wonderful and surprising.” For dinner, Muytjens heads to Mezze, Nancy Thomas’s farm-to-table restaurant. “It’s simple, but everything is special there,” he says. “The last time I went they had a martini with gin that was tomato infused. I am obsessed with finding my own bottle.”

Where to Load Up on Culture

To get your creative juices flowing, head to Shaker Mill Books, in West Stockbridge, and browse the collection of secondhand books and new editions. If you go on a Saturday, you can see their Barn, which is filled with bibliophilic art projects—specifically, furniture and clothing made out of books.

Before heading to the Berkshires, check out the websites of local music and performance venues, like Tanglewood, Jacob’s Pillow, and the Williamstown Theater Festival, to see what’s playing. For historic homes, Muytjens recommends Chesterwood, the house and studio of Daniel Chester French, the creator of the Lincoln Memorial. “You feel like you’re in the Age of Innocence,” says Muytjens. “The gardens are amazing and the studio is as it was. He had train tracks and put his sculptures on the platform and reeled them outdoors to see how they looked in the sun.” If you love anything Gilded Age, visit The Mount, Edith Wharton's stunning former residence.

You can’t miss Mass MoCA, a massive contemporary arts museum in North Adams. In Williamstown, the Clark Institute is a first-rate art museum with an impressive Winslow Homer room. Muytjens likes to picnic on the property’s outdoor sculpture grounds.

Where to Shop

If you want to pass for a local, head to Karen Allen, in Great Barrington, where Reichl buys the vast majority of her “rich hippie” clothing. Allen, a former actress who appeared in movies like Raiders of the Lost Ark, now knits. “It’s a mix of curated labels and colorful pieces that she made herself,” says Reichl. Eileen Fisher—the unofficial outfitter to Great Barrington’s female population—has a shop with a resale section as well as an area devoted to discounted samples from the label’s Design Studio, the arm that creates prototypes that often don’t end up in the next season’s line. For a different type of indulgence, walk to Farnsworth, a high-design marijuana dispensary that has something for everyone. If you need a host gift, look no further than their collection of vintage lighters.

The area shines when it comes to antiques. Two exceptional multi-vendor bazaars are Berkshire Galleries and Knollwood. “They have amazing stuff,” Muytjens says of the latter. “I’m obsessed with the 1800s bird baths and the vintage pillowcase collection.” Meanwhile, Rubiner is a Berkshire Galleries loyalist. “It’s so well curated," she says. "I recently got a Shaker-style kitchen cupboard that holds all our pretty pottery.”

Where To Have Fun After-Hours (and Recover the Next Day)

If you’re staying in a home with a kayak, Hadebe recommends an afternoon jaunt to Buckley Dunton, an unusually serene lake. Follow it up with a drink and show at The Dream Away Lodge, an old live-music venue in Becket with eclectic programming and bullseye cocktails. “It was once frequented by Joan Baez and Bob Dylan,” says Hedebe. “Now, it’s a lot of old hippies and young visitors to the area. It’s the perfect Berkshires mix.”

When you wake up the next morning with a slight hangover, head to Monument Mountain, a ten minute drive from downtown Great Barrington, for a satisfying hike.

When

There’s a Berkshires season for everyone. The fall is great for hiking and poking around in a cute New England town as the leaves change, but come back when it’s snowing for glorious skiing. The summer and spring are utterly dreamy, too.