Last month, I went up to New York to experience fall in Dutchess County, an area within the Hudson River Valley. This is the third year I’ve done an autumnal New England trip and I was pumped to finally check off an area I hadn’t yet visited. The Hudson Valley is a super easy trip for all my New York friends and family, and I’ve heard about it from them for years, but now that I realize it’s a doable weekend trip from DC, you can guarantee this won’t be my last trip.
My other fall in New England travel guides include: the Hamptons and Portland, ME.
Travel Guide: Fall in Dutchess County, NY
Dutchess County includes several towns you may have heard of: Rhinebeck, Beacon, Hyde Park, and Poughkeepsie (anyone remember that reference from Sex and the City?), and it has a range of landscapes from rural small town to stunning vistas to areas that are more suburban. You’ll find outdoor activities, historic homes, dining, antiquing, and basically everything that I know my readers love in a weekend trip itinerary.
Let’s go through the basics, then I’m going to share a step-by-step, day-by-day itinerary if you decide to go for a long weekend.
How to Get to Dutchess County
I’ll use the DC area as the baseline here. If you drive from DC, it’s roughly five hours — that’s usually the tipping point for me where it could be worth it to fly. We did, however, drive because I knew we’d be antiquing and it’s certainly easier to bring goods home if you have a car. Also, this itinerary is spread out enough that you’ll be happy to have a car.
Where to Stay in Dutchess County
We found Beacon and Rhinebeck to be the two most charming areas, so I would definitely try to stay in one of these places.
When to Go for a Fall Weekend in Dutchess County
We went to Dutchess County the second weekend of October and we were just getting into the height of leaf peeping season. The weather was cool, but not so cool that we couldn’t sit outside and enjoy the weather.
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Day One: Fall in Dutchess County
Stop One: Picnic on the Grounds of the Vanderbilt Mansion
We wanted to eat dinner at the Culinary Institute of America but, unfortunately it happened to be their alumni weekend so they were completely booked. Instead, we had a picnic lunch from their Apple Pie Bakery Cafe, which was scrumptious (don’t sleep on the macaron bark!). We ate on the grounds of the Vanderbilt Mansion, which is stunning. We hiked all the way back to the water, where we set ourselves up on a picnic table overlooking the river. It’s the kind of place where you see locals going on their power walks and tourists gawking at the incredible beauty of the land and buildings. Make sure to stop by the gardens — even in the fall, they are stunning with seasonal flowers.
Note: tours are currently limited at the Vanderbilt Mansion, so make sure you book well ahead of time!
Stop Two: Visit the Staatsburgh State Historic Site
Next, we stopped by the most stunning Gilded Age mansion — and one I’d never heard of before. Staatsburgh was the country home of Ogden and Ruth Livingston Mills and, now, it’s a grand mansion and an impressive display of 17th and 18th-century French decor as interpreted during the late 19th century. The guide did an amazing job of painting a picture of how guests would have traveled to the estate for the weekend and the fall activities that they would have participated in throughout the weekend — and I spent the afternoon daydreaming of how I can recreate this in the 21st century.
Stop Three: Stroll Through Rhinebeck
This was a quick stop, only because we’d read about how adorable Rhinebeck is. Had we had more time, we certainly would have shopped around and perhaps grabbed a bite to eat. We did, however, have a chance to grab coffee at Bread Alone Bakery and then popped in a few shops.
Stop Four: Grab a Glass of Wine at Rose Hill Farm
What’s a fall weekend without a stop by a winery? We grabbed glasses of cider and sat outside overlooking the autumn vistas at Rose Hill Farm and, if we were apple or pumpkin picking kind of people, we could have stayed around for the pick your own farm.
Stop Five: Dinner at Farmers and Chefs
After a quick stop by our hotel to drop off our stuff, we headed over to Farmers and Chefs for dinner. We snagged an outdoor table on this crisp evening and settled in with our cocktails. The Chicken Liver Pate and the Cacio e Pepe dishes were favorites of mine. Definitely order the Orange and Chocolate Mousse for dessert.
Day Two: Fall in Dutchess County
Stop One: Coffee and Pastries at Kelly’s Bakery
I spend far too much time looking for the best coffee shop whenever I travel, but that time was well spent once we walked into Kelly’s Bakery and took one look at the pastry counter. We got a babka muffin, a cinnamon roll, and I grabbed an orange cardamom iced coffee. Despite the branding on their website, the vibe inside is hip and industrial. It’s somewhere I would have loved to sit and stay for a bit, but we had big plans on the horizon…
Stop Two: Antiquing at the Stormville Airport Flea Market
I’d never been to a massive outdoor antiques show — until this one. The Stormville Airport Flea Market was an overwhelming experience at first. You walk in and there are rows and rows of vendors. You wonder which way to go or where you’ve already explored. I wouldn’t say it’s my favorite way to go antiquing, but it was a beautiful day and I walked away with a stunning chinoiserie planter. Once I got in the groove, I could have stayed for hours, but, again, our itinerary called.
Note: definitely bring cash! Very few vendors, if any, take credit cards.
Stop Three: A Flight and Food at Sloop Brewing Co.
After a busy morning at the antiques show and a quick stop by the Barn Arts Center for their Harvest Festival, we’d worked up an appetite, so we ended up at Sloop Brewing Co. Any brewery that has stouts on the menu is a win for me and Adam loved their signature IPA, Juice Bomb. But the real standout for me was their restaurant. The Sloop Brewing Co. Tasting Room and Restaurant has awesome pizzas, fries, and sandwiches — everything I was craving after walking around all morning and then downing a beer or two.
Stop Five: A Quick Run Through Wappingers Falls
We had some between lunch and dinner, so we drove through the tiny town of Wappingers Falls and stopped in two great shops. The first was Ruinous Revived, a shop dedicated to all things nostalgic, lush, and vibey. The next was Stone Bridge Antiques, which is your classic antiques store, where sifting through is necessary, but there were absolutely some diamonds hiding in there (and I’m still regretting that I left behind the most beautiful autumnal brown china).
Stop Six: Explore the Grounds of the FDR Library
Due to limited availability and restrictions, we weren’t able to tour inside the FDR Library, but we did explore the grounds. The gardens are absolutely stunning and there’s a view overlooking the surrounding rural land that’s worth the visit alone. It’s one of those views where you absolutely understand why they made their home here, and you wonder what it was like when they looked out on the same vista over one hundred years ago.
Stop Seven: Swing By Hyde Park Antiques Center
If there’s one antiques shop to stop by in the area, Hyde Park Antiques Center is it. There were so many incredible pieces here and, somehow, I only left with a few small decor items…but I’m still thinking about the lamps and dishware I left behind.
Stop Eight: Dinner at Essie’s Restaurant
We ended our jam-packed day in the Hudson Valley with dinner at Essie’s Restaurant, which blends Caribbean and Southern flavors with a modern American menu. First things first, our meal was made by the table next to us. I overheard them tell the waiter that they were celebrating their fifth anniversary and that the chef at Essie’s had catered their wedding before starting the restaurant. With their young son in tow, it was perhaps the cutest scene I’d seen in a while. But, eavesdropping aside, the food was excellent. You must get the Jambalaya Croquettes and the Jerk Ribs.
Day Three: Fall in Dutchess County
Stop One: Stroll the Walkway Over the Hudson
We woke up early on our last day in Dutchess County and laced up our walking shoes to walk the 1.25 miles and back over the Walkway Over the Hudson. It was a chilly cloudy morning, but the fall views from above the city are incredible and you can ready signs as you make your way across the bridge to learn the history of this former railway structure.
Stop Two: Grab Breakfast in Beacon
Let me preface this with: if we had known how cute Beacon is, we definitely would have planned for more time here. But, alas, we did not — plus, it was a rainy, cold fall day on our last day in Dutchess County.
However, we did grab coffee at Big Mouth Coffee as soon as we got into town and then satiated our hunger and sweet tooth with donuts from Glazed Over. I don’t even prefer cake donuts, but these were so yummy.
Note: Peaceful Provisions had delicious looking donuts, but they were sold out of the good flavors by the time we got there!
Stop Three: Explore Dia Beacon
We then spent an hour or so exploring the Dia Beacon museum. This place isn’t going to be for everyone, but both Adam and I enjoy modern art installations and each room here was both stark and thought-provoking. The massive size of the space and experiential nature of each piece makes it worth a visit.
Stop Four: Tour Bannerman Island
After leaving Dia Beacon, which was, of course, a perfect rainy day activity, we opted for a more outdoor experience. We took a boat tour on the Hudson River to Pollepel Island to tour the quirky structure that is Bannerman Castle. We had the most fantastic tour guide — a sophomore in high school! — who, in animated fashion walked us through the history of a rags to riches story, a castle built in haste to house military surplus goods, a massive explosion, and years of disrepair. It’s a bizarre place that feels a bit like a hidden gem on the Hudson.
As we departed the island, the rain began to pour, and, by the time we got back to land, we were soaked and in need of a warm meal.
Stop Five: Lunch at Ziatun
Luckily, we were able to snag a table at cozy Ziatun as our last stop before heading out of town. With warm pita and hummus to coat our bellies after a chilly morning on the water, we left the Hudson Valley full and happy — and ready to plan a trip back (with more time in Beacon and Rhinebeck, for sure!).
Recommendations by Category | Fall in Dutchess County
Where to Eat in Dutchess County
Where to Go Antiquing in Dutchess County
The Stormville Airport Flea Market
Where to Stroll in Dutchess County
Where to Visit in Dutchess County
Staatsburgh State Historic Site
Thank you to Dutchess Tourism for sponsoring this weekend trip! As always, all opinions are my own, and I’m so grateful to the brands that make this blog possible!
I have some extended family on my dad’s side in Poughkeepsie, and 10 years ago he and I went there for a weekend for cousin’s Bat Mitzfah! I remember we did the Walkway over the Hudson and it was just the coolest. This guide makes me want to go back as an adult!
xoxo A
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