Gilt trip
Dutchess County, New York, USA


‘I have made about 1¾ miles of road this season, opening entirely new and beautiful views,’ wrote the American painter Frederic Edwin Church to sculptor Erastus Dow Palmer in 1884. ‘I can make more and better landscapes in this way than by tampering with canvas and paint in the studio.’ Quite a claim, given Church’s status at the time as the most lauded artist America had ever raised. The star of the second generation of the influential Hudson River School of landscape painters and co-founder of New York City’s Metropolitan Museum of Art, Church channelled much of his great wealth into buying piecemeal 250 acres of land he had spent his formative years painting, ultimately crowning his estate in New York state’s Hudson Valley with a sublime hilltop villa called Olana, the views from which he painstakingly embellished with grand landscaping projects such as that he described to Palmer.

Church’s magnificent, largely self-designed 1870s Victorian/Orientalist villa opulently fuses colonial grandeur with influences brought back from his extensive travels in the Middle East, and its interiors remain as he and his wife Isabel furnished and decorated them. Standing before it (time a visit for sunset if you can) and gazing down across rolling pasture, lake and forest, thousands of whose native trees Church planted, and the majestic, two-mile-wide Hudson, with the hazy outlines of the densely wooded Catskill Mountains forming a softly jagged horizon, it’s still eminently possible to feel the sense of wonder at the region’s seemingly endless natural bounty that inspired his luminous and minutely detailed paintings.

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And while Olana sits a few miles north of the border in Columbia County, this is a feeling that will become familiar over the course of my Dutchess County stay. Today just 90 minutes by train or car north of New York City, Dutchess County was a favoured holiday home for many of the burgeoning new-world metropolis’s most dizzyingly wealthy families and is rich in mansions in vast, landscaped grounds from the late 19th-century Gilded Age. Now New York state historic sites, these transport visitors to an extraordinary moment in the history of the US for a generation of settlers amassing wealth at a rate that history had never seen outside royal families, and whose consequent sense of limitless possibility was the American Dream’s grandiose foundation.

In the 20th century, Dutchess County – like many Hudson Valley counties – increasingly became a popular second-home location for New Yorkers and a forever retreat for those leaving urban dwellings behind, with many still commuting weekly or daily to work in the city. The result is a network of communities, some proudly vibrant, some contentedly rustic, each enjoying its own version of gracious 21st-century living. All seem high on Church’s reverence for the land’s bucolic allure, while shaped to a greater or lesser degree by the Big Apple’s progressive liberalism. For visitors, the county makes an eye-opening extension to a short stay in New York City, or a destination trip in itself, especially enhanced with easy day-forays into other Hudson Valley counties, all of which have attractions and charming character quirks of their own.

Meanwhile, the natural magnificence that captivated those early champions endures. To this traveller, one of the US’s most distinctive attractions is that, even while in the thick of one of the world’s biggest and most frenetically urbanised cities, you’re never more than 90 minutes from a spot where you can gaze across vast stretches of scenery undeveloped enough that you can imagine what early settlers saw – and Native Peoples for millennia before.

Hiker and biker heaven

With mountain ranges to east and west, and the mighty, tidal Hudson on its western border, 825-sq-mile Dutchess County – which, tantalisingly, trailed the first fiery flashes of peak leaf-peeping season during my visit – comprises rolling farmland, dense old-growth forest, river-valley views and sweeping skies. It has four national parks, and dozens more national, state and local parks, between them offering 75 trail systems, making its landscapes a gift for hikers and bikers of all kinds. The Hudson also provides scenic opportunities for sailing, kayaking, wild swimming and stand-up paddleboarding, though it’s worth heeding the clue in the river’s Wappinger name Mahikannituck (‘river that flows two ways’), as tidal currents mean a level of proficiency in such watersports is advisable.

The sheer breadth of the thickly wooded local mountain ranges makes their rugged drama hard to appreciate from a distance. And while Dutchess County has its own mountains in the Taconic and Hudson Highlands ranges, visitors staying, as most do, close to the river – the north and east of the county remain as they have been for centuries predominantly agricultural – can sample their wild glories most easily just across the Hudson in Ulster County.

As I drove across the Mid-Hudson Bridge and towards the Shawangunks, they seemed to swell skywards, Inception-style, to reveal sheer sandstone steeps and towering crags. Swerving vicarious vertigo at the Gunks, some of the US’s premier rock-climbing cliffs, I took a dreamy woodland hike to Minnewaska State Park’s idyllic and people-free Awosting Falls, before heading up to the park’s visitor centre to pair views over Lake Minnewaska with my picnic lunch (nearly losing it to a nonchalant porcupine which ambled my way from beneath some shrubs).

I dug deeper, too, into the extraordinary lifestyles of the super-rich, late-19th-century settlers, some of America’s founding families, who holidayed here. A Dutchess County jewel is Staatsburgh, the 79-room Beaux-Arts fall-season retreat of old-money settler heiress Ruth Livingston Mills and her Gold Rush-minted husband Odgen Mills. My guide Don tactfully indulged me as I dug for more and more details of extravagance and excess as he described the lavish balls and society dinners the couple would host and the innovations their wealth afforded, such as a dedicated coal-powered electricity plant to wow their guests with electric lighting. The painstakingly preserved interiors – especially the French château-style entrance hall and the huge dining-room table set for dinner and framed by views of endless Mills-owned landscaping through tall windows – recreate a scale of affluence and grandiose aspiration whose audacious newness in the world can still be vividly felt here.

Other notable examples are the nearby, 85-hectare Vanderbilt Mansion National Historic Site, a classically colonnaded pile famed for its ‘millionaire’s view’, built by the eponymous family of railway tycoons. Then there are Wilderstein, Clermont, and Springwood, the latter the lifelong home of Dutchess County’s prodigal son, President Franklin D Roosevelt. The beloved family seat where he lived, worked and entertained dignitaries from all over the world is now supplemented on its 365 hectares of grounds by the Franklin D Roosevelt Presidential Library and Museum. Never short of ambition, the former president oversaw this building’s construction himself, and it was overhauled in 2013 to update its depiction of the depths of the Great Depression, the challenges of World War II and the progressive leadership style FDR, the US’s only four-term president, pioneered. Also scrupulously illustrated are the extraordinary contributions of his wife – and mother of his six children – Eleanor, whose human rights and equality work were ultimately recognised when she was made the inaugural chairperson of the UN’s Commission on Human Rights in 1946. The museum also works hard to stay current with temporary exhibitions and recently launched the fascinating Black Americans, Civil Rights, and the Roosevelts, 1932–1962, which will run for the whole of 2024.

Layered culture

Beyond this rarefied social stratum, it’s in Dutchess County’s diverse towns, villages and hamlets that its contemporary lifestyle becomes intriguingly apparent, and more of Dutchess County’s fascinating, multi-layered history reveals itself. Generations of Dutch, then German, then English settlers have left their architectural marks, as have early industrialisation and subsequent affluence, as can be seen in each community’s distinctive and charmingly organic miscellany of modest stone workers’ cottages, gracious colonial clapboard villas and red-brick Victorian-industrial structures, almost universally lovingly upkept.

Plutocrats’ country piles aside, landmark buildings include Quaker meeting houses that served as safe spaces for fugitive ex-slaves, ancient Dutch churches and the odd intriguing folly, such as the wildly eccentric, ruined Scottish-style Bannerman Castle, built in 1901 on a picturesque islet in the Hudson just south of Beacon to store military-surplus equipment. In chic Rhinebeck, meanwhile, the Beekman Arms claims to be the oldest continuously operated inn in the US and is thought to be the place where a War of Independence-plotting Alexander Hamilton first met Aaron Burr, the man who would later kill him in a duel.

And with each community’s distinctive architectural cocktail comes a signature vibe. Rich in historic low-rise red-bricks, stylish Beacon, for example, has a low-key party vibe easily sampled in its lively music venue the Towne Crier Cafe, the dapper Wonderbar adjoining the cute retro cinema the Beacon Movie Theater, and gay hostelry The Roosevelt Bar. Gorgeously groomed Rhinebeck’s 1:175 restaurant-to-resident ratio gives a clue to its good-living priorities, with the five-star Mirbeau Inn & Spa, complete with white Rolls-Royce to collect guests from nearby Rhinecliff railway station, the area’s most lavish wellness destination. And in the very north, tiny Tivoli, population 1,020, quietly punches way above its weight as a mini-magnet for artists and academics – although that may be in part down to the sterling work of Fortunes on the tiny main drag, named New York state’s best ice-cream purveyor by Food & Wine magazine. (Halva and honeycomb, anyone?) The accommodation offer is across the board, from large, big-name hotel chains, to, more typically, polished and unique boutique hotels, bed and breakfasts and, unsurprisingly, an embarrassment of elegantly appointed home rentals.

Culturally, lofty aspiration levels are sustained not only by New York City’s radiating influence on Dutchess County but by a wealth of illustrious college campuses too, which also, through their outstanding facilities, stir world-class public-view artistic offerings into the mix. Vassar College, in county seat Poughkeepsie, has the Powerhouse Theater, where Lin-Manuel Miranda workshopped what became his award-winning hip-hop musical Hamilton and which stages a six-week performance season each summer. And at the very least an Insta-must is Frank Gehry’s arresting 2003 Fisher Center, a space-age mega-pavilion, its sinuous stainless-steel shingles gleaming between towering ancient trees in the grounds of Annandale-on-Hudson’s venerated private liberal arts institution Bard College (alumni include Donald Fagen and Walter Becker of Steely Dan, Adam ‘Beastie Boys’ Yauch and Mia Farrow). Aside from attracting international music, theatre and dance talent in its year-round programme, the Fisher Center is also the hub of the locally adored seasonal festival SummerScape, whose cabaret Spiegeltent typically sees multiple appearances by New York City legend and Hudson Valley habitué Justin Vivian Bond.

LGBTQ+ life here, while low-key, is cosily embedded in the liberal community, with gay-owned businesses such as Poughkeepsie’s The Crafted Kup coffee house, Beacon’s metaphysical gift shop Witch Please by Les Loups de la Lune and The Amsterdam restaurant and bar in Rhinebeck high-street landmarks. Locals recount with pride that the mayor of New Paltz, just across the river in Ulster County, performed America’s first same-sex weddings in 2004 – seven years before the state legalised them. All sizeable communities have convivial annual Pride celebrations, from parades to performances to dance parties, which synch to build a swelling rainbow tide ahead of New York City’s big march on the last Sunday of each June, while a year-round programme of LGBTQ+ socials, performances, sports events and more in Dutchess and its neighbouring counties can be found on the website Big Gay Hudson Valley.

Beacon has another cultural ace up its sleeve in Dia Beacon, an outpost of the Dia Art Foundation and international gallery network and, at 15,000 sq metres, one of the biggest contemporary art exhibition spaces in the US. Housed in a vast red-brick former box-printing factory for the biscuit company Nabisco, it dazzles by its sheer volume, its immaculately rendered industrial rawness suffused with natural light through enormous windows. That same capacity enables it to house colossal works, such as the towering curved sheets of corroding steel of Richard Serra’s Torqued Ellipses series and a whole sub-gallery of Louise Bourgeois’ scary/sexy bronze and steel spiders, interspersed with meditative expanses of hushed empty space.

Home of ‘the real CIA’

Another revered institution is what locals call ‘the real CIA’, its establishment pre-dating America’s Central Intelligence Agency’s by just over a year. Based in Hyde Park, the huge, Hudson-side Culinary Institute of America hones the skills of aspiring chefs from all over the world, as it did those of Anthony Bourdain and celebrity chefs Kwame Onwuachi and Anne Burrell. It also has five public restaurants serving everything from consummate American grills and baroque patisserie creations to The Bocuse Restaurant’s exceptional modern French fine dining. Happily, many of its graduates launch their own Dutchess County restaurants, with Mirbeau Inn & Spa’s Willow by Charlie Palmer and Poughkeepsie’s Essie’s Restaurant, which showcases the Caribbean and Deep South traditions that chef Brandon Walker learnt from cooking with his family, stellar examples. On the wine front, suffice it to say that the Hudson Valley was the first wine country in the US, and local craft brewing and distilling scenes are also booming.

Agriculture was traditionally the county’s principal business and evolved organically, the breadbasket to an ever more demanding New York City. As such, it never tipped over into ultra-industrialised, broad-distribution production, and the head start this gave it on recent decades’ resurgence in locavore culture and organic farming drives a pretty much universally high-quality dining offer, whether in a smart restaurant, cosy bistro, at a pop-up at one of the wealth of local farmers’ markets or a gorgeously retro Americana diner, of which the county has many (with the American/Greek Yankee Clipper Diner in Beacon a standout).

Good food, principally of the farm-to-table variety, is a universal passion too. Such was my visit’s timing, I heard excited chat in numerous cafés, shops and bars about the imminent annual appearance of some of Montgomery Place Orchards’ 70 varieties of apples – and, crucially, cider donuts – at its roadside stall on Route 9. Another major buzz centred around the opening of a new 5,000-sq-metre sake production facility from premium Japanese brand Dassai, with stated ambitions to partner with US suppliers to make Dutchess County the birthplace of the first true American sake. Joining one of the first visitor tours, I heard of partnerships already forming with local restaurants excited to co-create new fusion experiences, pairing sake with American meats and cheeses, for example, as new avenues for local gourmet innovation. The tour itself is surprisingly compelling, and mesmerising through its combination of ancient, painstaking, by-hand techniques with a hi-tech setting worthy of Japanese starchitect Tadao Ando – a little like an immersive Zen Bond film directed by Tim Burton. As an extra bonus, the tasting that concludes the tour lets me mark my departure from Upstate New York with a draft that could hardly have been more apposite. Sweet, soft, complex and a little heady. Dutchess County, kanpai!

Photography by Grant Taylor, Martin Perry, Rupert Mellor, Heather Mcardle, Stephan Hengst and courtesy of Dutchess Tourism and New York State OPRHP

Get out there


… hire a car. There’s so much to see and do within short hops, and you can either pick up a rental in NYC or county seat Poughkeepsie – the 90-minute train journey there from the city is virtually at river level for much of the ride, making a lefthand-side window-seat pole position for glorious valley views.

… check out the ‘mobile passports’ for the Dutchess Tourism Trail Finder. Themed for cultural inspiration, local history, wineries, and restaurants, the passports suggest itineraries and offer some discounts.

get a bird’s-eye view. Whether you’re hanging from a cliff (in a fun, sporty way), surveying the scene from the Ferncliff Forest fire tower close to Rhinebeck, or cycling the iconic repurposed railroad bridge Walkway over the Hudson, the world’s longest elevated pedestrian bridge 65m/210ft above the river, the blessed local geography is manna to the eyes. You can even fly in an open-top 1929 biplane out of the Old Rhinebeck Aerodrome.


forget to honour your inner divine feminine. The extraordinary achievements of First Lady Eleanor Roosevelt, engagingly celebrated at her getaway Val-Kill, can overshadow other great local women, whose historic sites include Beacon’s Madam Brett Homestead and the Beatrix Farrand Garden at Bellefield.

expect to get a walk-in restaurant table at weekends. Book ahead, especially in summer, when a packed calendar of fairs add daytrippers to the full complement of weekly commuters rolling into the towns and villages.

feel you have to miss out on LGBTQ+ revelries just because you’re out of town. Beacon’s The Roosevelt Bar serves the community seven days a week, with drag hosted by Andramada on Fridays, while Poughkeepsie’s Reason & Ruckus bar hosts Dive Bar Disco every other Saturday. The Hudson Valley area is also home to queer art exhibitions and classes, sports clubs, river cruise parties and live music performances.

The inside track

Stephan Hengst and Patrick Decker

A lack of connected community among the Hudson Valley’s large numbers of queer residents inspired husbands Stephan Hengst and Patrick Decker to set up Big Gay Hudson Valley, at first an information website and now also a producer of diverse LGBTQ+ events – it’s as fabulous as Dutchess County gets.


Head further into the county and you’ll find spectacular vineyards and distilleries. Millbrook Vineyards & Winery and Taconic Distillery are great, but Milea Estate Vineyard really stands out.


Rhinecliff is home to one of our favourite places to hang out in the county. Kips Tavern has some of the best food, best service and best value around. And it always has a cool queer scene going on.


The Frances Lehman Loeb Art Center is incredible. It’s at Vassar College, which was originally women-only and has a strong queer history. Among its collection are works by Warhol, Haring and O’Keeffe.