Guide to Dutchess County, NY: Exploring the treasures (and Paul Rudd’s treats) hidden along the Hudson River

Towards the end of last year, as the leaves on the trees of New York were filling up the gutters, and the sights of Halloween peppered the sidewalks of small towns, I ventured north of NYC for the first time ever to the beautiful Hudson Valley Region.

It’s a place so beautiful, and filled with so much to see and do, that when you do make the trip, you’ll honestly wonder why on earth it took you so long to get out of the city and make it to this little slice of paradise.

Here’s your guide to one of the true hidden gems of America, and all the treasures you’ll find along the way.

Where is Hudson Valley, New York?

The Hudson Valley is a sprawling region, starting 150 miles above the tip of Manhattan, in New York’s state capitol of Albany, moving south to Yonkers, in Westchester County, about 20 minutes out of the Big Apple. If you’ve only ever spent time in Manhattan and the surrounding boroughs, you may be surprised at just how quickly the concrete jungle turns into some of the most beautiful scenery in the entire country.

There are 10 counties that make up the Hudson Valley, and for my recent travels in the region I spent my time in Dutchess County.

Dutchess County covers about 2072 square kilometres (800 square miles), running alongside both Massachusetts and Connecticut. Its county seat is Poughkeepsie, which at one point in time was the capitol of New York State (all the way back in 1777), and was where the state ratified the U.S. Constitution. Today, it’s as far North as you can travel on the MTA’s Metro-North line, making it exceedingly accessible by car and public transport.

How to get there

Once you’ve gotten yourself to New York City (with direct flights now possible out of Auckland, and connections available through any US entry hub), you’ll be able to get to Dutchess County in less than two hours.

In fact, the region is so accessible from NYC, it’s actually one of the terminus locations on the MTA’s subway system. They’ll get you as far as Poughkeepsie, with Metro-North operating three rail lines along the east side of the Hudson River, out of Grand Central Terminal in Manhattan: The New Haven Line, the Harlem Line, and the Hudson Line.

It will take you around two hours to get from Grand Central Station to Poughkeepsie – and is usually quicker than driving. Though having a car in the region would be helpful, there’s other public transport options, as well as Ubers and Taxis in the area.

Amtrak will take you further north than Poughkeepsie, and we travelled directly to Rhinecliff out of New York. Soaring past the Hudson River for the entire journey, right out of the tip of Manhattan, past the George Washington Bridge, is a sight to behold. Amtrak trains go pretty regularly, and you can look at the timetables HERE.

Where to Stay

While in Hudson Valley, we stayed in Tivoli, about 80 kms (50 miles) south of Albany, and 48 kms (30 miles) north of Poughkeepsie. This served as a perfect central location to tackle some of the best spots of the region. Tivoli was about 16 kms (10 miles), and less than 20 minute drive, from the Rhinecliff Amtrak station.

Our accommodation was the Hotel Tivoli (53 Broadway, Tivoli), a phenomenal boutique hotel, built into a century-old stone building. It feels like a classic hotel and bar you might find in any small town in Australia, where the bar is downstairs (in this case their incredible farm-to-table restaurant The Corner), and an assortment of comfortable rooms are upstairs.

The hotel is owned by painters Brice and Helen Marden, who have filled the hotel with their art collection, and have put thought into every aspect of the experience. From providing one of the most comfortable beds I’ve ever slept in (the pillows in particular were a godsend), with colours that match the aesthetic of the space; each of the ten rooms offers something a little different. No doubt regular guests would have their favourite, and ours was a room on the front end of the building, with the view of the hotel’s signage out our window.

The room has its own bathroom ensuite, filled with fluffy towels and fabulous amenities  – almost entirely high end local products, supplied by 2 Note Hudson. There’s a large still glass bottle of Connecticut’s Saratoga water, with glasses, as well as a local magazine Chronogram, sitting on a bench in our room.

An à la carte breakfast was included in our stay, with a daily hot option (this day it was scrambled eggs with bacon and potatoes) and granola and fruit to share, which were among the best tasting we’ve ever had. And as the picture above will show you, they don’t shy away from providing high quality mugs, bowls and cutlery. It’s the attention to detail that makes the Hotel Tivoli one of the best places to stay in the region.

For those who like their accommodation options in even older buildings, you can head to Rhinebeck, a five minute drive from Rhinecliff Amtrak station, where you’ll find the Beekman Arms & Delamater Inn (6387 Mill St, Rhinebeck). Beekman Arms is the oldest continually operating inn in the entirety of America. That’s 1766 for those playing at home – before the Revolutionary War! As you’ll discover through the article, it’s one of many establishments in the region that have lasted through the centuries.

Where to taste the sweet local produce

For those looking for some fresh fruit and produce, head to Montgomery Place Orchards in Red Hook, and their roadside market known historically as the “Wayside Stand” (4283 Route 9G, Red Hook).

It’s only open seasonally – from mid-May to Thanksgiving in November. They lean towards apples here – with some 70 types grown and on sale. But it’s also a place to enjoy a variety of fruit, from berries and peaches to watermelons – depending on what time of the season you arrive. They also sell a wonderful array of local produce at the stand, which dates back to the 1935 Dutchess County Fair, with jams, cheese, soap and even Apple Cider Donuts, which are honestly worth the trip alone. For more details about the market, head HERE.

If those donuts didn’t quell your sweet tooth’s desires, head to Rhinebeck’s fabulous Market Street and Samuel’s Sweet Shop (42 E Market St, Rhinebeck).

The candy store is co-owned by: The Walking Dead‘s Jeffrey Dean Morgan; his wife Hilarie Burton (whom you may remember from One Tree Hill); Paul Rudd, his wife Julie Rudd; actor Andy Ostroy and long time employee John Traver (whose favourite candy, fun fact, is Real Australian Kookaburra licorice).

It may seem unusual for a bunch of Hollywood types to co-own a sweet shop in upstate New York, though it is just about the story you might expect it to be. Originally called Samuel’s of Rhinebeck, and opening in 1994, after the owner Ira Gutner passed away in 2014, and the store faced closure, Morgan and Rudd – who call Rhinebeck home – decided to join forces to save the business. They changed the name to Samuel’s Sweet Shop, and the rest is history.

Though they are known to pour coffee from time to time, we didn’t see any of the famous faces in the flesh while we were visiting (on Halloween, no less!). But you’ll spot their mugshots throughout the establishment, telling you about their favourite treats or even being edible themselves, on the top of a house made Rice Krispies Treat.

Where to Eat

With ample fresh produce in the area, upstate New York and Dutchess County are filled with incredible dining options. And you don’t have to go far from Broadway in Tivoli to find it.

Look no further than The Corner at the Hotel Tivoli, who offer an impressive dinner menu Thursdays to Mondays, and brunch on Sundays 11am-230pm. The dinner menu features an impressive array of options, from steaks and seafood stews to duck breast and chicken tagine. Every dish I tasted was cooked to perfection, with an emphasis on local ingredients and impeccable presentation, which comes as no surprise given the quality of the Hotel itself. Also look out for Monday burger nights! You can see their menus HERE.

Across the street, you’ll find the Tivoli General (54 Broadway, Tivoli), which is owned and operated by an Australian born Cameron Price and his wife Andrea Shilling. They sell a highly curated selection of produce and groceries – including Meredith Dairy Goat Cheese (which Australian readers will know is as good as you get in that department), as well as coffee and a breakfast and lunch menu. Of course, flat whites are included on the menu, as are incredible toasted sandwiches, which we enjoyed on our way out of town.

Across the street, Fortunes Ice Cream (55 Broadway, Tivoli), is – I am told – worth the trip to Tivoli alone, with rotating flavours and dairy free options available.

The reason I never ate there was in part due to GioBatta Alimentari (69 Broadway, Tivoli), an Italian restaurant just up the road from the hotel, where you’ll find absolutely beautiful meals. We devoured some perfect calamari and  linguine vongole, and absolutely stuffed ourselves without leaving room for dessert.

If you need a nightcap, Traghaven Whiskey Pub (66 Broadway, Tivoli) is across the street, and offers the largest selection of Irish whiskey in the region.

Back in Rhinebeck, which is a 15 minute (10 mile) drive from Tivoli, you’ll find the farm-to-table restaurant Terrapin Restaurant (6426 Montgomery St, Rhinebeck), which sits in a former church built 200 years ago (in 1823) by Richard Scott as the First Baptist Church of Rhinebeck.

The restaurant, which opened in 1998 by Executive Chef/Owner Josh Kroner, was one of the first of its kind in the Hudson Valley, offering the farm-to-table that’s experience now something of a norm throughout the region. You can build your own sandwiches, enjoy soul food plates, and the grilled pork chop with apple demi-glacé, topped with maple-bacon almonds, is a specialty. I had the fried chicken plate, with potatoes and gravy, greens, and mac and cheese. It was the sort of soul cooking you wouldn’t necessarily expect in this part of the country, but it was divine. And the atmosphere of this 200 year old church only served to amplify that experience.

Speaking of experiences, there’s nothing quite like eating at Anthony Bourdain’s alma mater, the other CIA, the Culinary Institute of America (1946 Campus Dr, Hyde Park). Its main campus sits in Dutchess County, just north of Poughkeepsie. And in addition to being a school for the aspiring chefs of the region and the world, there’s also four restaurants on site where the public are welcome to dine.

American Bounty Restaurant puts a “focus on the seasons and products of the Hudson Valley”, Ristorante Caterina de’ Medici turns its attention to Italian cuisine, with wood oven pizza and rustic dishes, and the Apple Pie Bakery Café provides sweet and savory takeout options. We sat down at their contemporary French restaurant The Bocuse Restaurant, which at the time it opened in 2013, was the CIA’s first new restaurant in some 40 years.

Bocuse serves traditional three course, prix fixe menus, with $49 lunch and $59 dinner options. We bumped into someone high up at the CIA who recommended the black truffle soup to start, and it did not disappoint. Nor did the duck breast or the immaculately prepared and presented crepe cake – all three dishes of which you’ll see above.

It’s a way to have truly gourmet meals prepared by the next generation of chefs, at an affordable price. So you can understand why this is one of the hottest restaurants in town. All but the bakery require reservations, and you can see more details about the restaurants HERE.

Another city in the county that is a popular destination for locals and travellers, is Beacon. It helps that you’ll find one of the MTA-North stations here, making it one of the easier areas of the county to visit – especially without a car. It’s about an hour south of Tivoli, and you’ll be forgiven if you thought you fell right into a section of Brooklyn.

The café Homespun Foods (232 Main St, Beacon) came recommended, and with a fantastic burger and a lovely patio out back for you to enjoy the days of pleasant weather, I would pass that recommendation on myself.

Must See Museums

More than just great food, Beacon has situated itself as a must-visit destination of the region thanks to a fantastic arts community. This very much feels like the place people who grew up in Brooklyn end up buying property and raising their family.

Sitting under the gaze of Mount Beacon, there are marvellous places to eat, a waterfall at The Roundhouse, the only local hotel, hiking trails up the mountain, and a free loop bus through the area to keep everyone connected. If you grew up in Brooklyn, chances are you grew up without needing a car – and they seem to be trying to keep that spirit alive here.

And it’s here you’ll come across one of the world’s finest modern art museums, Dia:Beacon (3 Beekman St, Beacon). Focusing primarily on modern sculpture art (1960s onwards), with immersive sound installations and other experiences to enjoy, I would put it up there with the TATE Modern in London and MONA in Tasmania in respect of creating an unforgettable experience.

The incredible facility opened in 2003, built into a former Nabisco (National Biscuit Company) box factory. It’s a 300k square foot building, with 34k square feet of natural night, giving it the nickname “the daylight museum”. And depending on which hour of the day you visit, you’re going to see many of the artworks in different light (literally). So much consideration has been paid to the placement of the pieces, in respect to natural light in these huge open spaces, that it’s fair to call everything art. The building and its windows – even the parking lot has been made with key design features in mind.

Listen closely for a sound installation that takes over the whole space, starting ten minutes before the hour and gradually building through the whole building and outside. There’s entire rooms and levels dedicated to different artists, with the Richard Serra level one of my favourites. The way the light hit those sculptures in particular is just sensational.

To see more about the current artwork on display at this incredible museum, head to their official website.

If American political history is more your thing, the county is also home to the first Presidential Library, instituted by America’s 32nd President Franklin D. Roosevelt, known popularly as FDR, on the site of his family home.

Calling it a library may be misleading for international visitors – as this, and its visitor centre, are museums by any sense of the definition. His story is a remarkable one in the sense of how he transformed America into the place we know it to be today, and the visitor centre- which opens with a film about his history and landmark achievements – is an eye opening experience.

The visitor centre and the library, which re-opened in its current form in 2013, is run by the National Archives. The National Parks Service, meanwhile, operates the rest of the property. That’s 33 acres of scenic grounds, with incredible views – my favourite of which (top right) sits behind his house (bottom right), with a bench the President may have sat on to watch the sun set some 90 years earlier. And with those changing leaves, that was truly a sight to behold. Elsewhere, you’ll be able to pay your respects at the resting place of Franklin and his wife Eleanor Roosevelt

Entry to the grounds is free, and it’s a set $20 cost to enter the Library, Museum and FDR’s home, with children 15 years and under free.

You can also head 30 minutes north of the FDR Library and Museum, to the Hessel Museum of Art, which sits on campus at the Center for Curatorial Studies, Bard College. Students run this museum, a 1,600 square metre (17,000-square-foot) exhibition space featuring over 1,700 contemporary artworks and the Marieluise Hessel Collection.

(More) must see architectural delights…

Let’s keep on the Bard College campus, where you’ll find the Frank Gehry designed arts theatre space, The Fisher Center at Bard (Manor Ave, Annandale-On-Hudson). Tucked away on an unassuming lawn in the sprawling campus, the design of this building harks easy comparisons to another of Gehry’s famed theatres – the Walt Disney Concert Hall in Los Angeles, California.

The Fisher Centre hosts over 200 events every year across two adaptable performance spaces, with a mix of academic and professional programming. The architecture of the space is unique in how the musculature of the building – both interior and exterior – is very much on display.

The main room is the concert hall, which seats between 720 and 800 depending on set up, with a removable band shell, and douglas fir built into the space to assist with the acoustics. In addition to to music from one of the two resident orchestras at the music conservatorium, they’ll also put on dance and operatic performances in the space, with a massive performance wing off the side of the stage where they can have installations and performances of their own.

The second space, a 250 seat theatre, is renowned for the quality of its performances. In fact, the Broadway revival of Oklahoma! started as a student production here.

While this is a newer establishment, elsewhere in the region you’ll find plenty of historical landmarks to enjoy performances.

For one, on Market Street in Poughkeepsie, you’ll find The Bardavon 1869 Opera House (35 Market St, Poughkeepsie), which holds the crown of being the oldest continually operating theatre in New York State, and is home to the Hudson Valley Philharmonic.

Speaking of the 1800s, fans of The Guilded Age will find a number of estates from the period that remain open to the public in one form or another.

The closest thing to royalty that America has to offer, the Staatsburgh State Historic Site, and the Mills Mansion, is worth a visit, with its White House-esque, Beaux-Arts architecture, and maintained interiors that show what life was like for the wealthy Mills family that occupied the estate until it was donated to New York State in 1938.

In addition to tours of the building – which are $8 for adults, with some themed tours at $10 – the grounds hosts free concerts over the summer on the lawn, with a beautiful view of the Hudson.

For those who want more of this side of history, down the road you’ll find the Vanderbilt Mansion National Historic Site on the Hyde Park estate, and the Blithewood Estate and Garden, which sits on a 45-acre section of the Bard College campus.

Finding the scenic delights

Outside of the vast architectural splendour which peppers the region, the scenery in Dutchess County is as varied as it is stunning. There are vast open plains, bursting with colour, especially through October and November as the seasons change. There are waterfalls, lakes and of course the Hudson River in all its own splendour.

20 minutes from Poughkeepsie, you can visit the Minnewaska State Park, pictured above. It costs $10 to enter by car. After a short walk you’ll be able to make your way to the Awosting Falls, which provides a beautiful view from the top (as above) and below. You’ll also find another waterfall at Bard College, after a short 15 minute hike – look out for Zabriskie’s Waterfall along the Sawkill Trail (details of which you’ll find HERE).

While Awosting deposits directly into a small body of water below, Zabriskie’s makes its way into the Hudson – and within Dutchess County there are no less than three bridges that will take you across the river, including the world’s longest elevated pedestrian bridge, spanning 2.06 kms (1.28 miles) over the Hudson.

The aptly named Walkway Over the Hudson State Historic Park” reopened in 2009 after 12 years of renovations, having been used as the Poughkeepsie-Highland Railroad Bridge from 1889 until a fire in 1974. A 21-story glass elevator was added in 2014 and was where the main photo above was taken; the insert was taken from atop the bridge, looking south along the river. The elevator is closed for the winter months, and just reopened at the end of March. It provides incredible views, and is a popular trail for locals and tourists alike.

For us, this was where we brought an end to our journey, before heading back via Amtrak to New York City. In all, the Dutchess County region – and Hudson Valley more broadly – surprised with its diversity of experiences, as well as the wealth of well maintained (and utilised) history that dots its shores. This article barely begins to delve into the vast majority of that history, but really that’s something I hope you’ll experience for itself.

As much as I love New York City – and I do – now that I know this treasure sits within two hours of that fabulous concrete jungle, it’s hard to know if I can ever make a trip out there again with fitting in a visit to Dutchess County. And something tells me, it will have the same effect on you.

For more details about the venues and experiences featured in this article, visit them below:

Bardavon 1869 Opera House –
Beekman Arms –
CIA New York Campus –
CIA New York Restaurants –
Dia:Beacon –
FDR Presidential Library & Museum –
GioBatta Alimentari –
Hessel Museum of Art –
Homespun Foods, Beacon –
Hotel Tivoli & The Corner –
Mills Mansion / Staatsburgh State Historic Site –
Minnewaska State Park Preserve –
Montgomery Place Orchards –
Samuel’s Sweet Shop, Rhinebeck –
Terrapin Restaurant –
The Fisher Center at Bard –
Tivoli General –
Traghaven Whiskey Pub –
Walkway Over The Hudson –

The author visited the Hudson Valley as a guest of Dutchess Tourism, with accommodation provided by Hotel Tivoli. All photos by the author except for the Dia:Beacon shot, which has been supplied by the museum. Shots featuring the author taken by Dawn Hopper (in the mansion) and Debra Heath (at Homespun Foods). 

Any costs listed are in US$, and were correct at the time of printing, but subject to change. Visit the respective links to see the up-to-date costs.

Larry Heath

Founding Editor and Publisher of the AU review. Currently based in Toronto, Canada. You can follow him on Twitter @larry_heath or on Instagram @larryheath.