Taking the Scenic Route Around Upstate New York

Jessica Antola

A week of hotel-hopping in the Berkshires and Hudson Valley takes you through a wealth of culture, food, natural beauty, and some pretty spectacular properties.

As a British novelist who’s lived in Manhattan for a dozen years, I miss the English countryside—rolling hills, stately homes, bucolic farmland. So I decided to head out in search of reminders of home. And where better to seek intimations of old England than a region of New England (the Berkshires) named after the pretty English county of Berkshire?

I decided to brave the weekend hordes escaping New York City who turn the Taconic Parkway into a racetrack—you Americans, it seems, like to speed fast and furious toward your tranquility. But as the traffic thinned on Route 23 and my knuckles unclenched, I eventually edged over the Massachusetts border. New England immediately reminded me, at least on the surface, of old England—all tree-fringed country lanes, old villages, and clapboard lodgings.

The best way to get an overview of a region is from a mountaintop, and a climb from the Monument Mountain parking lot offers the perfect Berkshires introductory ramble. A sharp upward trail sends bracing country air into your lungs, and from the rocky peak an idyllic three-state panorama surrounds you. The trek takes 90 minutes, and as you return to your vehicle you’ll feel joyously alive. (Although due to a lack of country pubs, not entirely English.)

Being a writer, I headed next to the Mount, the Berkshires home of Edith Wharton. Here my nostalgia was partly slaked as I strolled through landscaped parkland that conjured Downton Abbey. The house itself is enchanting, and if you’re lucky enough to be escorted by Elric, one of the Mount’s guides, prepare to enjoy literary tales aplenty.


An installation by Trenton Doyle Hancock at Mass MoCA. Jessica Antola

Now it was time to check in somewhere luxurious. The Mount stands at the southern edge of Lenox, an opulent town flanked by two hotels that make up the grandes dames of the Berkshires. Blantyre (rooms from $435), the younger of the two, was built in 1902 and recently underwent a dazzling refurbishment. My British senses tingled as I pulled up amid 110 acres of lawns and wooded splendor to a huge manor built to resemble a Scottish castle. A stay at Blantyre is like a visit to Hogwarts, if Hogwarts were converted into a five-star hotel. I was quickly wooed by the wood paneling and found myself marveling at the leaded glass while feeling thoroughly lord-of-the-manor. A hard day’s drive was rewarded by live piano music and a refined beverage from the Dom Pérignon Champagne Salon in the shadow of a prettily ivied building. Should you wish to dine away from your lodgings, there are two excellent spots nearby: the Old Inn on the Green in New Marlborough, a candlelit 18th-century stagecoach rest stop; and the Prairie Whale farm-to-table joint, which occupies a rambling old clapboard house in downtown Great Barrington. However, Blantyre’s food is exceptional. Apart from the obvious oysters and lobster, you might dine on squab, venison, or pheasant, as if this were the deluxe version of a poacher’s table. And the wine cellar at Blantyre is truly extraordinary. I challenged the sommelier to find something interesting, and he returned with an Armagnac almost a century old. “We have all sorts of stuff down there,” he told me, sweeping the dust from his shoulders.

The next day, it was time to leave Blantyre for another singularly named hotel: Wheatleigh (rooms from $595). Built in 1893, Wheatleigh features stunning architecture based on a 16th-century palazzo. Even before you enter you are greeted by the sound of an ornate fountain that looks to have been ripped straight from a piazza in Florence. At once lofty and intimate, Wheatleigh lulled me into a happy stupor, even before the wine-soaked family-style dinner. The night I stayed, the theme was Greek wines, and while an almost never-ending parade of platters was passed around—Greek salads bearing fist-sized chunks of feta, lamb bright with the tang of lemon and wild oregano—I think most of us consumed several amphorae of the excellent vino, leading to the buzzy atmosphere of an exclusive salon.


The outdoor heated pool at Wheatleigh. Jessica Antola

If all this grandeur gets to be too much, head to the Inn at Kenmore Hall (rooms from $295), an 18th-century Georgian estate near Pittsfield. While hardly ungrand, Kenmore Hall retains a sense of intimacy, having only five rooms (plus a carriage house that sleeps four), each exquisitely adorned with a high-low mix of local antiques and modern furnishings. After pouring yourself a drink from the courtesy bar, take a seat in one of the inn’s two chic parlors and allow Dutch owner Frank Muytjens, the former head of menswear at J.Crew, and his partner, Scott Edward Cole, to graciously light you a fire, then sit back and have a chat about fashion and design. I picked up a few tips myself. Since my visit I’ve been buying a lot of antique brass candlesticks—“You can find them for almost nothing,” Muytjens told me. Also, Cole tipped me off about the only potpourri in the world that could be described as elegant. (It’s from the Italian perfumery Santa Maria Novella, and has wowed several guests at my house.)

Enough luxuriating. The Berkshires is famed for live performances: You might choose Tanglewood (world-class music and picnicking), Jacob’s Pillow (acclaimed dance productions), or Shakespeare & Company (renowned theater). However, I had other plans. An hour’s drive from Lenox, North Adams was once an industrial town, and in one of the area’s exfactories thrives a sprawling art space spread over 16 acres, the Massachusetts Museum of Contemporary Art, better known as Mass MoCA. Here you might encounter one of Sol LeWitt’s monumental wall drawings inside a hangar-sized gallery alongside the burbling Hoosic River, and if you follow the Hoosic a few miles to the west, you’ll come to Tourists (rooms from $199), a former hot-sheet motel converted into a Sea Ranch–inspired hipster redoubt (John Stirratt, the bassist from Wilco, is one of four co-owners). Keep driving west toward historic Williamstown, home of Williams College, and you’ll come to the Clark Art Institute, whose superlative collection ranges from Gilbert Stuart’s iconic portrait of George Washington to 32 paintings by Renoir.


From left: A dining room at Blantyre; a guest room at the Inn at Kenmore Hall. Jessica Antola

By now I was cultured out, and it was time for a rest. Turning back southward, I headed to the exquisite farmland of New York’s Hudson Valley, where I had a reservation at Troutbeck (rooms from $275), a former inn in Amenia that dates back to 1765. By another chattering brook, in a stone hostelry, I could have sworn I was in the Cotswolds. I strolled around the impossibly perfect grounds, my only regret the lack of time for a game of tennis at one of the two courts. Because, alas, it was time for dinner again—and surrounded by farmland, Troutbeck is a place where farm-totable makes proper sense, as a meal here will make toothsomely clear to you. (Oh, the pork chop!) One last trip to the bar, a few racks of pool in the sunroom. It was almost a shame to go to bed—except, what a bed!

I could have relaxed at Troutbeck for a week, but one final short trip took me to Hudson, New York, a former ghost town that has been transformed into a mecca of refinement. Innumerable antiques stores line Warren Street (Finch was a favorite) and plenteous cafés offer refreshment. As the evening approaches, here’s an idea—make your way to the Maker Lounge, a carriage house converted into a darkly sexy cocktail bar. From there, slink over to chef Zak Pelaccio’s Fish & Game for elevated Hudson Valley fare in a 19th-century blacksmith’s shop. And afterward, maybe slink back to the Maker for one more Charlie Chaplin (sloe gin, apricot, lime). Timothy Doyle, local antiques dealer, is playing the piano. Close your eyes: This could be England. Or, admittedly, something even better.