Weekend Wanders In The Hudson Valley: Exploring New York’s Backyard

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My Dutchess Story

My Dutchess Story starts in the Hudson River Valley ten years ago. We discovered New York’s backyard when looking for a few days’ escape from The Big Apple.  Our daughter was studying at New York University and having a whale of a time. We’d arrived in New York only to find her busy – honestly, kids! You fly over 10,000 miles and they’ve got a placement project with Google and a meeting with Hilary Clinton on campus to attend. Anyways, with a few days to ourselves, we set off to explore upstate New York.

Why visit Dutchess County?

In the charming Hudson River Valley, we discovered interesting and captivating homes and gardens. Though our visit was brief, the FDR Museum and Library left a lasting impression, especially the influence of First Lady Eleanor Roosevelt. It reignited my passion for American history and politics, bringing back memories of my college studies.

We stayed at the wonderfully historic Beekman Arms Inn in the attractive town of Rheinbeck. It was our American friends who insisted we would love the olde world charms of this historic Inn. They were right. It was straight out of an all-American dream movie to me, especially as you enter the White House-style hotel under huge American flags. You know how I love a memorable hotel with a wow factor!

We came, we saw, and we very much enjoyed the region’s grand homes, hotels, and gardens. With many more wanders in the beautiful countryside to enjoy, we knew we would return one day. 

Fast forward to 2023 and I’m back. This time as part of my solo travel US adventures invited by Dutchess Tourism.

Today Hudson Valley offers much for the visitor from a scenic boat ride on the Hudson to the Walkway over the Hudson. The region has further developed as a foodie’s destination. Farm-to-table dining, Farmer’s Markets, and even a Food and Wine Festival. All were a massively enjoyable part of my stay.

Won’t you come for a wander with me?!

Day One 

AM: Rhinecliff ~ Mirabeau Spa ~ Wandering Rhinebeck ~ Rhinebeck Farmers Market ~ Beekman Arms Inn

Lunch: Terrapin Restaurant

PM: Hudson Valley Wine and Food Festival ~ Franklin D Roosevelt Presidential Library and Museum

Dinner: Chipotle Poughkeepsie

Dutchess Country history

My return to Dutchess County gives me the chance to explore some of its 825 Square miles in the heart of New York State’s Hudson Valley region. I’m on the search for the promised ‘misty mountains, riverside hamlets, and farm-to-table dining’ and keen to understand more about the area’s history.

The first railroad arrived in the 1800s, a legacy that continues today. As I disembark my Amtrak train in Rhinecliff, 90 miles north of Manhattan, I’m warmly welcomed by Dawn from Dutchess Tourism.

Dawn loves her history and I am soon wrapped in the delights of Hudson Valley as discovered by the Dutch and German settlers. Anyone who loves “Hamilton: the Musical” will be chuffed to know, that Founding Father Alexander Hamilton has many connections to the region. And in his spirit, “I am not throwing away my shot.” We’re off exploring we’ve things to do, and people to meet!

Rhinebeck

The historic leafy village of Rhinebeck is worth a wander! I learned the town was originally called Ryn Bek, and was settled by Dutch colonials in the 1600’s. It’s named after Wilhelmus Beeckman who founded the town and his native Rhineland home.

Today it’s a charmingly walkable place, full of boutiques, art galleries, and over 30 restaurants and cafes. For more on Rhinebeck see Little Wandering Wren’s Instagram.

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Samuel’s Sweet Shop: 

We visited Samuel’s Sweet Shop, ranked the 5th best candy store in the USA by USA Today. It’s a nostalgic candy store, offering chocolates, old-fashioned candies, espresso drinks, teas, baked goods, and even a chance encounter with a celebrity or two!

The shop has a heartwarming history, saved by three families after the founder’s unexpected passing. Co-owned by actors Hilarie Burton, Jeffrey Dean Morgan, Paul Rudd, and Julie Rudd, and Andy Ostroy, with John Travers managing it.

Address: 42 E Market St, Rhinebeck, NY 12572

Rhinebeck Farmers Market

Voted Best Farmers Markets in the Hudson Valley with 40 vendors in summer and 25 at their winter indoor venue

Our visit to the Rhinebeck Farmers Market was the first opportunity to get to see some of the local and regional farm and agricultural products. Held in the town’s main car park, this is a popular hangout to munch, meet, mingle, and shop! We spotted cheese, charcuterie, fruit, wines, honey, mushrooms, Alpaca yarns, and sheep milk yogurt.

Open May – December, every Sunday 10-2 pm

Address: 61 E Market St, Rhinebeck, NY 12572

Looking at all the delicious food made us hungry! It’s not an easy choice to select a restaurant in Rhinebeck, there are so many!

LUNCH: Terrapin

Terrapin Restaurant was voted Best Farm-to-Table Restaurant and Best Bistro of the Hudson Valley so a top choice.

Offering local, organic, authentic dining it is in an interesting setting found in an old church. I chose a burger (I am in America after all!) from their casual Bistro menu. I study my tomato in a new light when I’m told that tomato was picked this morning!

 Address: 6426 Montgomery St, Rhinebeck, NY 12572,  

Hudson Valley Food and Wine Festival 

How lucky was I, that my time in the Hudson Valley coincided with one of the region’s biggest and most popular annual events at Dutchess County Fairgrounds?

The Hudson Valley Food and Wine Festival celebrates the food and wine culture of New York. Entry gives access to food and craft beer and wine tastings with over 200 vendors from across the state. The vendors often have Festival special prices, making this a great place to stock up! This is a popular hang-out with locals too, with everyone enjoying the live music, cooking demonstrations, and seminars on a variety of culinary topics. 

Top Tips! Dates for 2024 have been announced as 07 – 08 Sep 2024, mark it in your calendars now. Look for Groupon discounted entry ticket.

With so many to choose from it seems a little unfair to highlight any, but these were a few vendors that caught our eye and we enjoyed chatting with:

Millbrook Vineyards & Winery

Millbrook is considered one of New York State’s top wineries, and called Hudson Valley’s flagship Winery by the New York Times, so this was a perfect start for our wine tasting! They have been producing award-winning wines on its 130 acres for more than 30 years. We sampled the Tocai Friulano a variety native to northeastern Italy and one of many wines available for tasting from Chardonnay, Pinot Noir, Cabernet Franc, and Riesling.

A visit to Millbrook Winery gives you vineyard views and views of the Catskill Mountains (and a big tick for those misty mountains I was promised!)

Address: Millbrook Winery, 26 Wing Road, Millbrook, NY 1254

Whitecliff Vineyard Artisanal – Sustainable – Authentic – Vegan

Established in 1998 Whitecliff Vineyard was one of the most popular stands we went to. With a stellar reputation, this family-owned and operated vineyard and winery consistently wins more international awards than any other winery in the Hudson Valley. A large banner proclaims Winner, Winery of the Year 2022.

Address: 4150 Route 23, Hudson, NY 12534

Soukup Farms

I loved meeting Jennifer and Mark from Soukup Farms, I mean who doesn’t love Maple Syrup? For starters, I had no idea Maple Syrup production was so big in this region. Silly old me only tends to think of Maple Syrup in Canada. What do I know?!

This third-generation family started as a hobby and now has a production of 3000 Taps. We tasted their Maple Syrup and if you visit their farm you can see the maple syrup production from sugar bush to bottle and take a tour. As well as going home with some shopping, they have developed a unique product range from Maple Syrup!

Franklin D Roosevelt Presidential Library and Museum

As mentioned this is my second visit to Franklin D Roosevelt Presidential Library and Museum and it will never be enough. The museum starts with copies of letters written to the President and ends with a wander through his extensive collections from stamps to coins to rare books and model ships.

‘The story of the Roosevelt presidency, from the Great Depression through the New Deal years and World War II, is presented here in vivid and tangible fashion’.

FDR grew up with a privileged childhood on the banks of the Hudson River. entered politics only to endure illness and a lifetime of paralysis after a heroic battle with polio. As President, he led America out of the greatest economic depression in history and guided the Allied Powers to Victory in WW2

Eleanor Roosevelt known as the First Lady of the World, improved the lives of millions as a reformer, teacher, journalist, and political activist.

Plan to spend a least a couple of hours here and afterward take a wander in the grounds of Roosevelt Estate in Hyde Park New York.

For more photos see Little Wandering Wren’s IG Post.

Special Exhibition

The museum’s special exhibition gallery offers changing exhibits on a regular basis. The Current exhibition: Black Americans Civil Rights and the Roosevelts is on display until December 31, 2024

Century-old formal rose gardens and perennial beds closed by a wall provide the setting for the simple monuments marking the burial sites of the President and Eleanor Roosevelt.

Address: 4079 Albany Post Road, Hyde Park, NY 12538

Day Two 

AM Walkway over the Hudson ~ Hudson River Cruise

Lunch: Bread Alone Bakery

PM Vanderbilt Mansion ~ The Culinary Institute of America

Dinner: Crew Poughkeepsie

Walkway over the Hudson

We started our day at the elevated Walkway Over The Hudson, we took the elevator up! This gives a really nice perspective of the bridge.

The New York State Historic Park is the world’s longest elevated pedestrian bridge towering almost 65 meters above the Hudson River spanning over 2m across and connects to 32 km of hiking and biking trails. The walkway is part of the Empire State Trail system which connects New York City north to the Canadian Border and northwest to Niagara Falls. 

Top Tip! Elevator access on the East side of Hudson gives a cool view.

For more photos see Little Wandering Wren’s IG Post

Hudson River Cruise

All aboard – The river is calling! So what’s a must-do activity in the Hudson Valley? For me, it is to cruise the Hudson River.

It was so relaxing soaking up the last days of summer on Rip Van Winkle II. Their 90-minute narrated sightseeing cruise was really well done. It was informative and told some of the stories from the history of the region.

I especially loved the Hudson River lighthouses. The views of the Catskill Mountains are gorgeous. We also get a glimpse of the many historic waterfront mansions dotted along the river that you can visit.

For more photos see Little Wandering Wren’s IG Post

Address: DOCK 1, East Strand Street, Kingston, NY 12401

Lunch: Bread Alone Bakery

This popular bakery in Rhinebeck comes highly recommended by the locals I met. We had the chance to stop for lunch for a handmade organic bread sandwich and coffee.

Vanderbilt Mansion National Historic Site

I loved wandering the scenic Hudson Valley region taking a peek into the lives of the rich and famous, who have chosen this area of upstate New York for their county getaways. Supposedly their modest homes, these mansions from the Gilded Era are anything but and if you love history and seeing how the other half lived, you should not miss a guided tour of the Vanderbilt Mansion National Historic Site.

Frederick Vanderbilt was not the only wealthy industrialist to build a country palace. But this striking estate, his home from 1896 to 1938, remains one of the best examples from the Gilded Age. Your visit should include a stroll through the formal Italianate gardens and hiking trails for spectacular views of the Hudson River.

Address: 81 Vanderbilt Park Road, Hyde Park, NY 12538

Top Tip! Don’t forget to stop at Millionnaire’s View where the famed postcard  Currier and Ives painted in the late 19th Century

For more photos see Little Wandering Wren’s IG Post.

The Culinary Institute of America

If you get a chance to eat at the world’s premier culinary Institute you should, I hear it’s fabulous. The Culinary Institute of America (CIA) was founded in 1946 and your dinner could be served by the next Anthony Bourdain!

You have several choices from Italian at RISTORANTE CATERINA DE’ MEDICI, fine dining at THE BOCUSE RESTAURANT, or casual dining at APPLE PIE BAKERY CAFE. All the details and how to make a reservation are found here.

Address: 1946 Campus Drive, Hyde Park, NY 12538-1499

Dinner: Crew Restaurant & Bar, Poughkeepsie

Talking of CIA Graduates, we were happy to meet Owner and Executive Chef Thomas Kacherski in person at his Crew Restaurant & Bar for dinner We talked about his Farm to Table and Sea to Table menus devoted to local and organic fare. Crew is known for its casual and modern environment with a dedication to local and organic fare. Highly recommended if you are in the area!

Address: 2290 South Rd, Poughkeepsie, NY 12601

Where I Stayed

Courtyard by Marriott, Poughkeepsie

The Courtyard By Marriot Poughkeepsie offers 137 spacious newly renovated guest rooms with a large desk and WIFI, microwave, and coffee machine. Breakfast was not included in my room rate but the cafe by reception offered good coffee and avocado on toast.

This stay is a good choice for those wishing to be close to Poughkeepsie Train station. Walkway over the Hudson, Vanderbilt Mansion, and local vineyards and breweries!

You can see my room tour here on ‘Little Wandering Wren’s YouTube Channel

Beekman Arms Inn

If you are looking for colonial charm and a historic stay with lovely grounds in the walkable town of Rheinbeck check this out. Opening its doors in 1766 it has been welcoming guests since before the Revolutionary Wars.

Address: 6387 Mill Street, Rhinebeck, New York

Traveling To the Hudson Valley Region

It’s easy! I came by Amtrack Train 90 minutes from New York City

Hiring a Car

Ten years ago we hired a car and I drove out of New York. Yes, I thought that was pretty gutsy of me too! For those that are asking, Australians drive on the left, as in the UK, while the US drives on the right. 

My husband and I decided that it was better for me to drive and for him to navigate rather than the other way around. This was designed to avoid the usual family fun of “which way now, you’ve got the map!” arguments that married couples the world over used to have each holiday!

By Train

In 2023 I’m alone and on the train. Just for the record, Mr. Wren is alive and well and enjoying his golf and wildlife in Thailand but not an invited part of my solo adventures. This time I very much appreciated the ease of an Amtrak train!

Which is better Amtrak or MNE Train?

Metro North East (MNE) train departs from NY Central Station, it is slightly cheaper but a longer ride. My preferred option was the Amtrak Train from New NY Moynihan Train Hall at Penn Station.

Whilst leaving from NY Central Station is an iconic departure station, the new Moynihan Train Hall is a destination delight in its own right.

This is such a lovely way to start your travels. At Moynihan, you can stock up for your ride at the food hall, (check out Magnolia Bakery of Sex in the City cupcake fame from Gate 5/6) and relax in the Amtrak waiting area.

After the train winds its way along the Hudson River you will arrive in Poughkeepsie in 90 mins. Two hours will get you to Hudson where I jumped off. 

Top Tip!

Add in the complimentary Red Cap Service where you are taken to the platform with a porter and boarded ahead of the masses for a real VIP start to your train ride. Note: Tips are always expected and appreciated in America, I’m told anything from $5 upwards is the go!

Amtrak Waiting Rooms

If you show your train ticket you can wait in the designated waiting area, until the platform is announced. Those in the know sprint off quickly, aiming for a seat on the left-hand side for the best views of the Hudson River.

My Amtrak Rides

I took three train rides around the region, each was bang on time and the only issue was getting my heavy suitcase up into the overhead luggage rack.

NYC New York Penn (Moynihan Train Hall) to Hudson, NY (130 minutes)

Hudson to Rhinecliff (25 mins)

Poughkeepsie to NYC New York Penn (Moynihan Train Hall) 90 mins

A Note on Luggage

I wasn’t travelling light, in my defense, I was in America for over a month and luckily I didn’t have a problem at any point mostly due to the helpfulness of the average American! Chivalry is not dead on the Amtrak trains, I say ‘wear a big hat, sport a foreign accent, and most solo Sheilas will be right!‘

Top Tip: Be aware of luggage restrictions on trains and travel as lightly as you can! Apparently, Amtrak tells me the overhead compartments are to store carry-on bags 25 Ibs or less. For luggage that is heavier, they do have a designated area in each train car.

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Final Thoughts

I’m thrilled to add a new chapter to My Dutchess Story with a return to the Hudson River Valley after a decade. New York’s backyard offers a rich experience for history enthusiasts, foodies, and outdoor adventurers. I can’t wait to explore more mansions like Staatsburgh State Historic Site, hike the Empire State Trail more, and enjoy a wander in Ferncliff Forest. I so fancy a spa day at Mirabeau Spa, take a biplane ride at Old Rhinebeck Aerodrome, and savor apple pie at the Apple Pie Bakery Cafe CIA. This won’t be my last visit, for there’s still so much to do here.

As Alexander Hamilton said, “There’s a million things I haven’t done. Just you wait.”

Full disclosure: Little Wandering Wren was an invited guest of Dutchess Tourism. All opinions are my own.

Follow us on Social Media: Find more photos of my travels and stories on Instagram @littlewanderingwren.

For more on my previous visit to Hudson River Valley see Victory FDR Style.

The keen foodies amongst you will note the Bocuse Restaurant at the Culinary Institute of America, this French restaurant is named for the most famous chef in France, Paul Bocuse. We came across Paul Bocuse in Wandering Lyon; 48 Hours with a Lyon City Card.