Sloop on Hudson River in Dutchess County

Dutchess County:
Dream land


Ninety minutes north of Manhattan, Dutchess County in Upstate New York’s Hudson Valley offers majestic, rustic landscapes studded with opulent monuments to a foundational moment in modern American history. In between lie characterful towns and villages whose charm and culture – and heartfelt LGBTQ+ welcome – punch way above their weight.

“Many people move to the Hudson Valley because they want to escape the big cities, most typically New York,” says freelance marketeer Stephan Hengst. “And what’s great is when they come upstate, they bring with them a lot of arts, culture, education and creativity. And they start opening businesses and building new networks, and suddenly you have a very diverse, eclectic community that does some pretty amazing things.”

Reasons to settle in this part of the world don’t require much imagination. Bordered to the west by the mighty Hudson River, the 825 sq mile/2140 sq km Dutchess County is framed on two sides by mountains and comprises rolling pastureland, lush old-growth forest and endless views from its gentle riverside hills. With dozens of national, state and local parks, the county’s unspoiled landscapes today magnetise hikers, bikers and climbers.

The great escape

It’s on some of those riverside hills that the first generation of New York City (part-time) émigrés created perhaps the county’s biggest headline attraction, a collection of palatial holiday retreats that evoke the unprecedented extravagance and luxury of the Gilded Age, and the vaulting aspiration that shaped the American Dream. Among the most jaw-dropping are the 79-room Beaux Arts mansion at Staatsburgh State Historic Site, and the nearby Vanderbilt Mansion, both set in vast, spectacular grounds and both offering tours whose guides are happy to dish on the owners’ decadent lifestyles and rapacious social climbing.

The most famous, however, is Springwood, the former home of Dutchess County’s prodigal son, President Franklin Delano Roosevelt and now the Franklin D. Roosevelt Presidential Library and Museum. A monument to the progressive leadership of America’s only four-term leader, the estate also diligently documents the extraordinary human rights activism of his wife Eleanor, whose own house Val-Kill, rumoured late-life love-nest of the first lady and her close friend Lorena Hickock, can be visited close by.

Over the course of the 20th century, Dutchess County became a popular holiday-home location for more and more New Yorkers, and today is home to large numbers of residents who commute daily or weekly to the city. For the visitor, this proximity makes the county a great extension to a city break, although there’s plenty to do here to fill a whole holiday, and more attractions and inviting communities within easy reach in neighbouring counties.

This migration brought with it cosmopolitan tastes, progressive values and wealth that have shaped a network of communities from sleepy hamlets to manicured villages to bustling towns, each with its own distinctive brand of stylish, gracious living. Beacon’s historic red-brick streetscapes, for example, bristle with hip boutiques and cute bars and restaurants, while dining hotspot Rhinebeck exudes a refined, preppy charm and boasts some stunning clapboard colonial villas.

Culture meets cuisine

The county is also home to several venerable institutions which play their parts in its rich culture. The 161,000 sq ft/15,000 sq m Dia Beacon is one of the biggest contemporary art exhibition spaces in the US. The building, a converted packaging factory, is a showpiece in itself, its vast halls a masterclass in minimal architectural restoration, and among the monumental works there are extraordinary pieces by Louise Bourgeois, Richard Serra and Michael Heizer. Another is the mythical Vassar College in Poughkeepsie, whose beautiful collegiate campus includes the Frances Lehman Loeb Art Center, its huge collection comprising works by Andy Warhol, Georgia O’Keefe and Keith Haring. Here too is the Powerhouse Theatre, where Lin-Manuel Miranda workshopped his hip-hop musical Hamilton before it became a worldwide smash hit.

Close to Annandale-on-Hudson meanwhile is the illustrious liberal arts institution Bard College, whose Frank Gehry-designed Fisher Center, a surreal, curvaceous stainless-steel-clad concert hall, draws leading international music, dance and theatre talent year-round. The Culinary Institute of America in Hyde Park is another establishment that deliciously enriches local culture daily. Anthony Bourdain trained here, and the massive riverside campus has four restaurants which are open to the public, including the renowned modern French fine-dining spot The Bocuse Restaurant. The first of three ‘CIAs’ across the country, it’s perfectly placed to tap into the county’s stellar agricultural traditions, which were honed as demand from an expanding New York City for outstanding produce grew. The region was also the US’ first-ever wine region, and its wineries thrive still, many offering polished visitor experiences, as do a growing number of craft breweries and distilleries.

Dive deeper into Dutchess

To get to Dutchess County, you can hire a car, picked up either in New York City, the airport, or the county seat Poughkeepsie. Our recommendation is the Hudson-hugging, 90-minute train journey from Manhattan that beams glorious river views to your seat… it’s a must. Find out more >

Dutchess County has a growing number of accessible parks, recreational activities, events and sensory-friendly experiences. They’re proud of their homegrown ThinkDIFFERENTLY initiative, which strives to create a supportive destination for all. Find out more >

Everyone is welcome in Dutchess County! So it’s no wonder that the LGBTQ+ community has long found it to be a friendly, accepting environment. On top of everything that makes it a fascinating destination, there are LGBTQ+ events and goings-on throughout the year. Find out more >

Queer as folk

And while perhaps not obvious to the untrained eye, Dutchess County’s LGBTQ+ scene is in rude health. “Queer people have been moving here for ages,” says Stephan, “but because there used to be no designated bars or parties per se, I’d hear a lot of them say they felt disconnected, and ‘How do I meet other gay people here?’”

A keen socialite and consummate networker, Stephan’s response was, with his husband Patrick Decker, to set up Big Gay Hudson Valley, at first a Facebook group, and now a website and event production company.

“We were lucky in that we’ve always had a lot of overlapping social circles and we knew there was lots of cool stuff going on, LGBTQ+-run businesses, hospitality, resources, theatre, art exhibitions, parties and so on. So we set up Big Gay Hudson Valley to promote it all in one place and bring people together. And now we put on events, from pop-up bar nights to more elaborate productions with amazing venues like the Vanderbilt and Locust Grove estates, the Beacon movie theater and the Cunneen-Hackett Arts Center in Poughkeepsie,” says Stephan.

“Not that there wasn’t plenty going on already. Vassar College for example was originally exclusively for women and has a long legacy of queer presence in the community. Mary-Kay Lombino, curator at its Francis Lehman Loeb Gallery, has spent most of her career curating queer art. And did you hear about the SummerScape season Bard College puts on every year? A big part of that is the Spiegeltent. And the programming there is gay. Gay, gay, gay, gay, gay.”

Plan your trip

To help plan your next luxury trip, visit or speak to your travel advisor. Whatever your tastes, there are many brilliant places to stay in Dutchess County, everything from chic boutique hotels to charming bed and breakfasts.

Photography courtesy of Dutchess Tourism, unless otherwise stated

This article is in partnership with Dutchess Tourism

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