“The Rolling Stones came, the Beatles, [Jimi] Hendrix, they all came up here to party with him. This place was, like … really crazy.”
I’m 90 minutes north from the heart of New York City, sitting inside the guard house of a $70 million 1000-hectare estate that was once the temporary home of 1960s psychedelic revolutionary Timothy Leary.
I’m sharing a bottle of cabernet franc made just across the valley at Millbrook Winery with a man who has looked after this estate for near on 50 years.
“Here we were, not two hours out of NYC and there were hippies turning up every day, and rock stars too, there were 50 people sleeping here every night. Forget Woodstock, it was this county that was the craziest place in America,” he says.
“The psychedelic counterculture was not created in California,” New York historian Devin Lander concurs. “It was created in Millbrook [in Dutchess County].”
Half a century or so on, Dutchess County keeps flying under the radar. NYC receives 65 million visitors a year – while two hours east, hotel rooms in the Hamptons are booked out the whole northern summer.
But I’m here midweek in summer and I have the whole county to myself (New Yorkers will spoil this solitude, come the weekend). Yet, I took an Amtrak train – from mid-town NYC – for barely 90 minutes to get here. And rock stars and movie stars live here – or did (think: David Bowie, Liam Neeson, Meryl Streep, Paul Rudd, Uma Thurman, Al Pacino).
This might be America’s best-kept secret midweek destination. The moment I detrain, I’m taken: The big city seems a lifetime ago.
I’m deposited in a hamlet called Rhinecliff (Julia Roberts’ actor brother, Eric, was recently a resident), and walk down its leafy main street. There’s not much here but a picturesque grocery market called The Epicurean where locals gather; some record podcasts inside, in a tiny studio within the store.
I know this because I purchased a local cider and am drinking it on a seat outside and I’ve met every local coming in to shop. It’s that kind of place. They appear to be mostly artist types, refugees from the big smoke, keen for a quieter life, but not ready to head out to pasture.
We move down the street to local bar, Kips Tavern, which looks across the Hudson River into wilderness. No one appears to miss the city.
I’m not staying here – there’s no accommodation, even if my new-made friends might house me.
I travel seven minutes east instead to Rhinebeck, Dutchess County’s best-known town, though hardly a name that registers beyond NYC.
This county is a gathering of historic hamlets linked to the earliest days of modern-day America (Rhinebeck, for example, was established in 1686), spread among the first genuine wilderness outside NYC. There’s breweries, wineries and distilleries to visit in between all that forest – bears and beers, I like that.
There’s certainly a level of sophistication I expected this close to America’s largest city: My hotel is a French provincial-style spa resort, Mirbeau Inn and Spa, built next to the longest continuously-run accommodation in the US, the Beekman Arms.
The Beekman Arms in Rhinebeck is the US’s oldest continuously run inn. Photo: Dutchess Tourism
It’s where Chelsea Clinton got married in 2010. But except for the odd flash of mega bucks, it doesn’t feel like that sort of place.
There’s a down-homey feel to it all; staff at my favourite cafes remember my name, and my order (which, incidentally, is the best tasting latte in the US).
I could spend my days just driving through the county because it’s that pretty; but there’s plenty to do here.
I take a scenic flight in a 95-year-old biplane at the Old Rhinebeck Aerodrome to understand the scale of the wilderness, then travel for lunch to the planet’s most revered cooking college, Culinary Institute Of America, housed within a 70-hectare, 19th-century Jesuit School beside the Hudson River.
For less than $US50 ($72), I eat a three-course French meal prepared by the world’s greatest chefs-to-be at a school where the likes of Anthony Bourdain learnt magic.
But the whole county reeks of this kind of creativity; there’s four drive-in theatres with the most charming of them, Four Brothers Drive-In, set around a margarita bar where former resident Ethan Hawke is often seen.
Much of the area looks more like England than the US. Photo: Dutchess Tourism
Even in tiny little hamlets removed from the rest of the county, like Wassaic with barely 200 residents, locals have converted a decrepit old seven-storey wood grain elevator into the oddest art gallery (Wassaic Project) you’ll find in the country (there’s art produced by artists-in-residence on every floor accessible only via creaky wooden steps).
I move on from my hotel in Rhinebeck to the century-old Hotel Tivoli on a main street that looks like a movie set.
People line up next door at an ice-cream shop, and there’s a small town quaintness about the place that makes me wish I was staying for longer. I know I’m in Dutchess County when I step inside and find an eclectic collection of art and furniture (it’s owned by a painting couple with a penchant for collecting art).
Dinners out on its century-old, wrap-around verandahs as the tiny town kicks into life in the early evening (then finishes by 10pm), eating farm-to-table produce grown within the county, is as big a night round here as anyone needs (or gets).
Five days later, I’m back on the train south. And just like magic, I’m standing opposite Madison Square Garden in NYC’s mid-town wondering if all of this was really just some Timothy Leary-style psychedelic trip.
The writer travelled courtesy of I Love New York and Dutchess Tourism