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Dutchess County New York: A Gay Trip to Mid-Hudson Valley

Dutchess County New York: A Gay Trip to Mid-Hudson Valley

New York doesn’t end with New York City’s borders. During our trip to the Big Apple before World Pride 2019, we traveled north to the heart of New York State, the Mid-Hudson Valley region. We have been overwhelmed with a welcoming environment, calmness, and gay-friendliness. So, it was an easy task to put together this city trip weekend journal to introduce you to the heart of New York State the best way. Because, you know, New York is New York, right? Well, not quite… We boarded a Metro-North Railroad train and immersed ourselves into the county’s creativity, unexpected excellent cuisine, and omnipresent historical past. So, enjoy our gay travel journal of Dutchess County, New York, and see the gay-friendly Mid-Hudson Valley through a couple of men’s eyes.

– paid collaboration with Dutchess Tourism –

Our gay trip to Dutchess County, New York

Our gay adventure to Dutchess County, 1.5 hours north of New York City, was all about the natural beauty of the Hudson Valley’s blossoming spring nature and exploring the small towns. We could spend some relaxing days by the Hudson River and in the Catskill Mountains, enjoying delicious farm-to-table, organic food at various restaurants and the Culinary Institute of America. We could also learn about the legacy of Eleanor and Franklin D. Roosevelt as well as the stunning historical and contemporary art and architecture of Bard College, the Fishers Center of Performing Arts, and the museum Dia:Beacon. Curious? Let’s get started!

Dutchess County Upstate New York spring nature blue sky garden river view gay couple, a couple of men © coupleofmen.com
Gay Travel Bloggers Couple of Men enjoying Dutchess County Upstate New York © coupleofmen.com
Flying with KLM Royal Dutch Airlines © Coupleofmen.com

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By Train from New York City to Beacon

The trip from New York City to Dutchess County couldn’t be easier. After four exciting days in Manhattan, we jumped on the MTA in Grand Central Terminal and enjoyed our ride on an almost empty train up north. Our Tip: Get your train ticket at one of the ticket counters in the main hall and take a short walk to the right platform. If you can’t find your way, ask one of the friendly staff members at the information desk, located near the famous golden clock at the top.

Gay Reise Dutchess County Gay Travel Dutchess County Going upstate with an MTA train from Grand Central Station in New York City to Dutchess County © Coupleofmen.com

Right in the center of the gorgeous main hall of Grand Central Terminal, which should not be confused with Grand Central Station. The silver, shining train passes through the underground world of Manhattan before surfacing again in Harlem and continuing its journey along the Hudson River northbound. Next stop: the little town Beacon.

Gay Reise Dutchess County Gay Travel Dutchess County We are impressed by the cultural and architectural heritage of Dutchess County © Coupleofmen.com

Day 1 Beacon, Rhinebeck, Annandale-on-Hudson

DIA Art Exhibition | Beacon

In Beacon, the first thing we did was start our day with Breakfast at Glazed Over Donuts, a small, family-operated company that makes delicious donuts with special toppings. But no time to waste since we had a special appointment at the DIA:Beacon museum, exhibiting art from the 60s to the present in a former Nabisco box printing factory.

Gay Reise Dutchess County Dutchess County Upstate New York © coupleofmen.com
Gay Reise Dutchess County Take you time at DIA in Beacon because there is so much to explore in the exhibition spaces © Coupleofmen.com

Our highlights: going behind the glass to admire the gigantic art pieces by Michael Heizer embedded in the ground and the immersive sheets of steel by Richard Serra, arising into the space of the old factory building. Everyone who doesn’t arrive in a car (like us) can catch the shuttle bus from Beacon’s train station.

Gay Reise Dutchess County We were able to go behind the glass to admire the gigantic art pieces by Michael Heizer from closeby © Coupleofmen.com
Gay Reise Dutchess County Highlight No2: The immersive sheets of steel by Richard Serra arising into the museum's space © Coupleofmen.com

Plan your trip: Check here for more info, the opening days & hours >

Gay Reise Dutchess County Karl is impressed by the size of the art pieces at DIA Art Exhibition in Beacon, New York © Coupleofmen.com
Gay Reise Dutchess County Dutchess County Upstate New York © coupleofmen.com
Dutchess County Upstate New York © coupleofmen.com
Dutchess County Upstate New York © coupleofmen.com

Denning’s Point Distillery | Beacon

If you are in Beacon and Gin-Lovers like us, you should not miss a visit to Denning’s Point Distillery. Why? The company has a good atmosphere, and their spirits (especially the Gin) are delicious. No wonder they won for three consecutive years the award for the Best Hudson Valley Distillery! Denning’s Point is home to an old 19th-century building offering tours, tastings, and special events. Although we could not visit the place during weekends, we got the tip for our blog to mention the open blues jam sessions every 2nd and 4th Saturday of every month from 4-7 pm. Check their website for more details. Cheers!

Gay Reise Dutchess County Great 9 Gin it is! This bottle of delicious Gin made at Denning's Point Distillery made it all the way home to Amsterdam © Coupleofmen.com

Not into Gin? No problem. We also visited the Plan Bee Farm Brewery for a beer tasting with Family Emily and Evan Watson. Their goal is to brew 100% New York State ingredient beer grown on and around the farm in Poughkeepsie, New York. The special and unique sour taste of the beer is just another reason for the growing Plan Bee Farm beer fan community.

Oliver Kita Chocolates | Rhinebeck

Aware, exquisite, passionate, joyful, powerful, conscious – this is the philosophy of Dutchess County’s sweetest artist Oliver Kita. We all know about Karl having a sweet tooth, so a stop at the Oliver Kita Artisan Chocolate store during our trip was just obligatory (and worth it, Karl whispers). The cute little store on Market Street in Rhinebeck offers its organic chocolate bars and fine delectable chocolate creations to Hudson Valley visitors and locals.

Gay Reise Dutchess County Selfie moment with Oliver Kita, the master of chocolate in Dutchess County's Rhinebeck © Coupleofmen.com

Each level of the tasting experience reveals a distinct layer of sensation, featuring flavors of flowers, herbs, citrus, non-native fruits, berries, nuts, and spices. A cute little place of enjoyment and the best souvenir for family and friends with a sweet tooth like Karl… really, he loves chocolate!

The best organic chocolate bars and fine delectable chocolate creations at Oliver Kita Chocolates in Rhinebeck © Coupleofmen.com

Fisher Center & Bard College | Annandale-on-Hudson

On the road north from Rhinebeck towards our hotel in Tivoli, we passed by just another highlight of Dutchess Country: The Richard B. Fisher Center for the Performing Arts at Bard College in Annandale-on-Hudson. The first reason why any LGBTQ+ traveler should stop at this location is the magnificent and unique architecture designed by Frank Gehry. He is also the man behind the Dancing House in Prague, the Walt Disney Concert Hall in Los Angeles, and the Guggenheim Museum in Bilbao, Spain.

Gay Reisen Dutchess County "The Center" is located in Annandale-on-Hudson offering extraordinary arts experiences all year long © Coupleofmen.com

Secondly, the Fisher Center (as it is commonly referred to) offers its visitors extraordinary arts experiences, which is unusual for such a small town. The third reason has everything to do with summer: Since 2003, the Fisher Center hosts the annual Bard SummerScape festival featuring seven weeks of world-class opera, theater, dance, cabaret, film, and music.

Gay Reise Dutchess County Gay Travel Dutchess County Hand-in-hand in front of the The Richard B. Fisher Center for the Performing Arts at Bard College designed by architect Frank Gehry © Coupleofmen.com
Gay Travel highlight in Dutchess County: The Fisher Center © Coupleofmen.com

Gay-friendly Dutchess County Art Hotel Tivoli

However, before we tell you more about our adventure, we would like to introduce you to our gay-friendly accommodation, the Art Hotel Tivoli, situated in the town of Tivoli, located in the north of Dutchess County. The charming hotel rooms in this century-old building are filled with an eclectic collection of furniture, lighting, and art pieces that the owners have collected over the years. Brice and Helen Marden, big art lovers and artists themselves, ensured that every room and space in the hotel had an individual atmosphere.

Gay Reise Dutchess County Gay Travel Dutchess County Our room was bright offering a geat view of the cherry blossom and surrounding mansions © Coupleofmen.com

We enjoyed a complimentary breakfast at the farm-to-table restaurant The Corner, which featured homemade granola, freshly baked bread, free-range eggs, and a lovely hot coffee during our stay. Just everything we needed to get ready for our day in Dutchess County. Tip: If you are a light sleeper, bring your earplugs, as the building is an old mansion with some cracks and occasional creaks.

Gay Reise Dutchess County Art in every room: The Hotel Tivoli in Tivoli, New York is like a museum in itself with unique art pieces in every rooom © Coupleofmen.com

TripAdvisor: Hotel Offers Beacon | Hotel Offers Rhinebeck | Hotel Offers Poughkeepsie | Hotel Offers Hyde Park

Gay Reise Dutchess County Selfie in front of the gay-friendly Art Hotel Tivoli in Tivoli, New York © Coupleofmen.com Spring, Blue Sky, Old Mansion, Gay Couple Travel Blog
Gay Travel Guide New York City © coupleofmen.com

 New York Travel Guide

Jeder kennt New York, das Tor zur Neuen Welt, das auch Neues Amsterdam genannt wird! Heute kennt jeder den Staat New York wegen New York City, Sex and the City und natürlich wegen der Stonewall-Unruhen vor 50 Jahren. Wo soll man übernachten? Was kann man unternehmen? All diese Infos (und noch mehr) haben wir in unserem Gay Travel Guide für New York zusammengestellt!

Plane & buche deinen New York Trip >

Day 2: The Catskill Mountains – Poughkeepsie – Hyde Park

Explore Nature & The Catskill Mountains

Most well-established New Yorkers like to escape the busy city life occasionally upstate. One reason, undoubtedly, is the beautiful nature and stunning views of the Hudson River Valley. The county of Dutchess, which spans the east side of the Hudson Valley, opens up the view, especially from the northern part of Dutchess, over the county of Hudson and, distantly, the Catskill Mountains.

Gay Reise Dutchess County Spring view of the Hudson River Valley in Dutchess County © Coupleofmen.com

After early morning breakfast at our hotel, we hit the road to get a glimpse at one of the New Yorker’s favorite destinations for a day trip. Coming from Tivoli, we crossed the Hudson River over the Kingston-Rhinecliff Bridge, passed through the Dutch Colonial Town of Hurley, and reached the Awosting Falls at Minnewaska State Park Preserve Shawangunk Mountain ridge.

Gay Reise Dutchess County Walking hand-in-hand to the Awosting Falls at Minnewaska State Park Preserve © Coupleofmen.com
Hand in hand in Gay Travel Dutchess County © Coupleofmen.com

Unfortunately, we didn’t have so much time to spend there since we still wanted to see so much more, but the view of the Catskill mountains on our way back to Poughkeepsie was stunning. Definitely on the list for our next trip to Dutchess!

Gay Reise Dutchess County Sitting by the Awosting Falls at Minnewaska State Park Preserve on the Shawangunk Mountain ridge © Coupleofmen.com
Happy at Trixie Motel in Palm Springs © Coupleofmen.com

Gay Travel Index 2025

The Berlin-based Spartacus informs LGBTQ+ and queer travelers about how gay-friendly a holiday destination is according to several ranking factors and criteria.

Which country ranks first? Where is it safe to travel to as a gay and LGBTQ+ traveler?

You can use the GTI to prepare for your gaycation and as a guide when choosing a holiday destination.

Go to the 2025 Gay Travel Index >

Coffee to go for a spectacular view | Poughkeepsie

Gay-owned and delicious: The coffee at The Crafted Kup in Poughkeepsie is one of the best coffees in town, if not in Dutchess County. We had the opportunity to meet Tanner Townsend, owner of The Crafted Kup, who provided us with insight into his work, the snacks and coffee, and shared some thoughts about LGBTQ+ life in Dutchess County. For him, living here is not about going out or enjoying an active gay scene. New York City has plenty to offer to fill those needs. But when you want to enjoy nature and take a little break from the overwhelming energy of NYC, then Dutchess County is the perfect getaway or place to call home. One last coffee to go, and off we went to see the world’s longest elevated pedestrian bridge in Poughkeepsie, Walkway Over the Hudson. Next stop: American History!

Meeting Tanner in his coffee shop during our gay travel Dutchess County trip© Coupleofmen.com

The Legacy of the Roosevelts

You know us. We are eager to learn new things, especially when directly or indirectly connected to human rights and the LGBTQ+ community. During the preparations for our trip, we came across former US president Franklin D. Roosevelt and his wife, Eleanor. For those who are unfamiliar with President Franklin D. Roosevelt, also known by his initials FDR, he was a member of the Democratic Party and the 32nd President of the United States of America from 1933 to 1945. The biggest challenges of his presidency were handling World War II and being diagnosed with poliomyelitis (at this time). Together with Abraham Lincoln and Georg Washington, FDR is one of the most influential and greatest US-American presidents. Since he was born in Dutchess County in Hyde Park, we had to visit some historic monuments, too. There, we also learned about another Roosevelt, who was at least equally important to history, but for human rights and the support of the LGBTQ+ community, Eleanor Roosevelt.

desk of Eleanor Roosevelt in her house on Val-Kill

Val-Kill – Eleanor Roosevelt National Historic Site

Our first touchpoint with Roosevelt was a visit to Val-Kill, the Eleanor Roosevelt National Historic Site, the first and only historic site dedicated to a U.S. First Lady. As the name Roosevelt might already reveal, the family of the Roosevelts has a Dutch heritage, which Eleanor preserved by naming her later permanent residence Val-Kill (Dutch: loosely translated as “waterfall-stream”).

Gay Reise Dutchess County Happy to learn about American FEMALE history: Selfie moment in front of Eleanore Roosevelt' Val Kill © Coupleofmen.com

But who was Eleanor Roosevelt? During our tour with a representative from the National Park Service, we learned about her unconventional, proactive political role as First Lady (FDR’s “eyes, ears, and legs”), her dedication to her daily newspaper column, “My Day,” and her role as a mother of six children. After her husband died in 1945, she became an early civil rights activist, serving as an appointed delegate to the United Nations General Assembly and helping to establish the Universal Declaration of Human Rights.

Gay Reise Dutchess County Daan is noticeably impressed: So many important people of World's history met Eleanore Roosevelt in Val Kill - like John F. Kennedy © Coupleofmen.com

She was also the first chairperson of the United Nations Commission on Human Rights, among other notable positions. There is much more to learn about her, but you have to visit Val-Kill. A tip for your Dutchess County bucket list!

Gay Reise Dutchess County Selfie with our tour guide at Val Kill: Don't miss a thing and join a tour with a representative from the National Park Services at Val Kill © Coupleofmen.com

Franklin D. Roosevelt Presidential Library & Museum

For many US citizens, a must-do in a lifetime; for us Europeans, totally unknown: the significance of the 13 presidential libraries across the USA. The first one ever created is the Franklin D. Roosevelt’s Presidential Library and Museum in Springwood, Hyde Park. There, we could learn all about the Roosevelt presidency, from the Great Depression through the New Deal years and World War II, illustrating Franklin and Eleanor Roosevelt’s relationship with the American people.

Gay Reisen Dutchess County Learning about American history at the Franklin D. Roosevelt Presidential Library & Museum © Coupleofmen.com

Many U.S. Americans travel around the country to visit all presidential libraries to better understand the decisions, the historical context of the states, and the people’s relationship to the president and his family. Just a short walk from the library, we visited the Franklin D. Roosevelt National Historic Site and the graves of Franklin and Eleanor Roosevelt, set within a rose garden and interested in US-American history? Please put it on your list!

Gay Reise Dutchess County Gay Travel Dutchess County Selfie with Eleanor and Franklin D. Roosevelt (FDR) in front of the Museum © Coupleofmen.com
Gay Travel Dutchess County highlight: Franklin D. Roosevelt Presidential Library & Museum © Coupleofen.com

The Culinary Institute of America | Hyde Park Restaurants

Hungry? So are we. Time for dinner, but not just anywhere! Dutchess County is home to The Culinary Institue of America. Cooks from all over the world come to the cooking school in Hyde Park to learn the fine art of creating a culinary treat and embark on a taste adventure. We had a reservation at The Bocuse Restaurant to test classic French cuisine, American style.

Photo of the impressive main building of the Culinary Institute of America at Hyde Park © Coupleofmen.com

The best thing about the institute and the connected restaurants is that they are all cooked and served by individuals in education, which gave us an unexpected insight into their educational process of becoming professionals. The Bocuse Restaurant is a unique and exciting, world-class dining experience. Our Tip: Go for the Table-Side Ice Cream, made right at your table with liquid nitrogen! Yummy!

Creative and delicious dinner creation at The Bocuse Restaurant with fine french cuisine © Coupleofmen.com

Another dinner spot we can recommend is the Terrapin in Rhinebeck, known for its excellent farm-to-table menu. We had a terrific time there, and the cocktails suggested by the waiter were extraordinarily delicious! Make sure to check it out!

Gay Reisen Dutchess County What an experience: Delicious and educational! While having dinner at the Culinary Institute of America, we could watch cooks learn their profession! © Coupleofmen.com

Gay Travel Dutchess County – from NYC to Mid-Hudson Valley and back

We took the MTA train back to New York City, which, again, brought us along the scenic Hudson River, passing by the Military Academy at West Point: beautiful views of the river valley, and, all the way in the distance, the skyline of Manhattan.

It was an extraordinary New York adventure and a perfect way of mixing some relaxing days between the busy big-city life of NYC. We hope to come back one day to see the rest of the Hudson River Valley in New York State.

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Gay Reise Dutchess County Gay Travel Dutchess County Dutchess County Upstate New York © coupleofmen.com

Do you want to know more about travel news from the LGBTQ + community? Follow us on InstagramThreadsTikTokYouTube, and Facebook! See you around in the United States of America, Northern America, and on one of our next gay pride trips worldwide! Karl & Daan.

Please note: This trip was made possible in close collaboration with Dutchess County Tourism, Delta Air Lines, as well as the valuable tips and assistance provided by our wonderful readers, followers, and friends from around the world. Nevertheless, our photos, videos, opinions, and writings are our own, as always.