A Fabulously Fall Weekend in Dutchess County

It’s safe to say that autumn is my favorite season. To me? It feels more of a fresh start than even New Years! The crisp air, the leaves changing, apple and pumpkin harvests – all of everything “quintessentially fall” – gives me all of the feels. Being that this was the first year I wasn’t abroad for the majority of autumn, I knew I wanted to see the fall foliage as much as I could and was thrilled when Dutchess County Tourism invited me for a fabulously fall weekend in Dutchess County! I loved my stay in Dutchess County and outlined the itinerary below!


Have a tasting at Millbrook Vineyard & Winery:

Millbrook Vineyard and Winery has been named, “the Hudson Valley’s flagship winery” by The New York Times and “a great place to visit” by The Wall Street Journal – which are hardly endorsements to brush under the rug. I came to learn that in the 30 plus years that they’ve been operating, the Dyson family (owners of Millbrook) have acquired properties in both Italy and California in which they collectively produce between 10-15,000 cases of wine – annually. This endeavor has been extremely successful because not only are some of the wines award winning, but they’ve also received recognition from publications such as The New York Times and Bon Appetit Magazine.

My tasting was of six different Millbrook wines (three white and three red) and it was the first tasting I’ve ever had where I enjoyed every wine that I tasted. Jean, the host of my tasting, also went into some fun facts not only about Millbrook Vineyard and Winery but also the area, and about New York State! Not only were the wines delicious but the overall experience was a great way to kickstart my weekend in Dutchess County.

(left) The Millbrook Hunt Country White and (right) a view of the vineyard and fall foliage.

An aerial view of Millbrook vineyards (and beyond!) and the fall foliage.

Tour Wings Castle:

Wings Castle is the brainchild of artists Peter and Toni Ann Wing – who began building the castle (which remains a work in progress to this day!) in 1970. Today, Wings Castle is a bed and breakfast and almost a museum of sorts, as the castle (which is also a home) has been built with over 80% of recycled materials! Wing’s Castle also offers short tours (about 45-60 min) showing the intricate details all around the property from the mosaics to the stained glass to the pool (which is a real-life moat!). During the entire tour I kept asking, “and he built this?” because it’s mesmerizing that someone hand built the property.

The exterior of Wings Castle.

(left) Some of the (hand built!) stained glass windows and (right) the cottage which is available for rent across the street from Wing’s Castle.The cottage is the perfect place for a fall photo op!

 Dinner at Essie’s Restaurant:

Essie’s Restaurant in Poughkeepsie is owned by executive chef Brandon Walker who was inspired by the idea of elegant yet casual dining and his Modern American menu was inspired by international flavors and his family background in from the Caribbean and American South. Chef Walker uses modern techniques but pays homage to the area with local, seasonal ingredients that promote the local food economy while also showcasing the best ingredients the Hudson Valley has to offer. And, man, did they have a lot to offer.

My dinner at Essie’s Restaurant is one of the best meals I’ve had all year! My trip to Dutchess County ended up being the week after a family member passed away and without bringing the whole mood of this article down – Chef Brandon Walker served up the comfort food I was craving, with delicious twists! Not only that, but the blend of vintage pieces with reclaimed wood features and industrial touches in the dining room also set a super cozy and inviting mood.

Legit everything on the menu made me smile from the inside out; from the local heirloom tomato crostini (top left) to the grilled octopus (top right) to the perfectly prepared fish (bottom left) to the hangar steak (bottom right).


The Roundhouse is not only a boutique hotel but also an award-winning American restaurant and event space that can accommodate up to 200 guests. The historic property overlooks a beautiful creek and waterfall and is in the charming town of Beacon, New York. The hotel at the Roundhouse is held in two buildings and rooms range from “deluxe” to “suite” to “penthouse”. My deluxe room was super spacious with a mid-century modern and contemporary style with two large (custom made) beds, a desk and dresser as well as a large leather chair.

Some of my favorite features of the property were the super soft alpaca blankets, plush bathrobes, back-lit makeup mirror, in-room Keurig coffee machine and mini bar with snacks and beverages available for purchase. The Wi-Fi was also super-fast and the complimentary hot breakfast (included with all stays!) was not only a perfect way to start the morning but the views of the fall foliage over the waterfall were gorgeous!

The exterior of one of the buildings of hotel rooms at the Roundhouse.

Breakfast at the Roundhouse Restaurant, overlooking the waterfall.


Tour of Locust Grove Estate & Walk the Gardens:

Locust Grove is a historic estate, museum and nature preserve and was the former home of inventor Samuel F. B. Morse (yes, the man who invented Morse Code!). Morse and his family owned the home as their summer retreat and the main mansion is a villa that was inspired by Italian countryside architecture.

Today, the Estate is open to the public year-round and features over 15,000 pieces of furniture, paintings, artworks and more that once belonged the Young Family (the last owners of the Estate). There are daily tours operated of the mansion (and I’ve heard that is particularly special around the holidays!). I had a wonderful tour with our guide, Richard, who had the best one-liners, ever! The 125+ acres of gardens and grounds are also open for, “the enjoyment, visitation and enlightenment of the public” at the bequest of Annette Innis Young, the last member of the Young family to live at Locust Grove.

Some of the fall foliage at the gardens of Locust Grove.

The estate at Locust Grove.

The tower of the main house at Locust Grove Estate (left) and the perfect fall foliage photo op (right).

Lolita’s Pizza:

Lolita’s Pizza was actually suggested to me by Brandon Walker, the chef at Essie’s and his endorsement was understood the moment the scent of the warm olive appetizer hit my nose. Serving up antipasto, Neapolitan style pizza, handmade pastas and perfectly crafted cocktails – Lolita’s is a great stop for lunch (or dinner!) – especially on a chilly autumn day. The dishes are exactly what you’d want to order to fill your stomach while simultaneously soothing your soul. Do as I say, not as I did, and save room for dessert! My only regret was not having room for more than just a single bite of the delicious dessert.

(left) The mushroom pizza with margherita pizza in the background and (right) the olive and mixed green salad starters.

 Tour and Cider Tasting at Fishkill Farms:

Fishkill Farms is a 270-acre apple orchard and vegetable farm in East Fishkill, owned by the Morgenthau family for over 100 years! Not only do they offer apple and pumpkin picking experiences (quintessential autumn activities) but also sell homegrown organic veggies and eco-certified produce (all year round!)

Katie took us on a great tour around the farm, from the greenhouse that was drying their crop of peppers, to the area where they’ll be growing strawberries come spring and especially around the apple orchard! The farm was a great stop on my Dutchess County autumn itinerary and the home-brewed cider at Fishkill Farms was the warm treat I needed after the chilly outdoor activities. You can visit Treasury Cider to learn about a cider tasting of your own!

The peppers drying in the greenhouse.

Apples growing in the Fishkill Farms orchards.

Fishkill farms also offers the perfect fall photo-op with pumpkins as props!

 Walkway Over the Hudson for Sunset:

The Walkway Over the Hudson was originally built as the Poughkeepsie-Highland Railroad bridge in 1889 and was transformed into the 1.28-mile linear park that it is today. The walkway is open from 7:00am to sunset so if you’re visiting for sunset be sure to pay attention to the time the sun sets and be there at least 30 minutes before, much more if you want to walk the entire Walkway. Autumn is known for its beautiful sunsets which make the Walkway Over the Hudson the perfect place to catch the sunset and take in some fall foliage.

Perfect fall foliage over the Hudson River from the Walkway Over the Hudson.


Museum Visit at Dia: Beacon

Dia: Beacon is housed in a former Nabisco box printing factory and the building in itself is a work of art and pays homage to the industrial past that defined Beacon as a manufacturing city. The steel, brick concrete and glass make the perfect home for the contemporary installations – which are naturally lit with over 34,000 square feet of skylights. The Dia: Beacon has a strict photography only for “personal use” policy which means the perfect way to experience Dia:Beacon is on a trip of your own!

All in all, Dutchess County in the heart of the Hudson Valley is the perfect destination for some fall foliage and autumn fun. From the local businesses, farm to table eats and especially with the optimal leaf peeping options – you can’t go wrong!

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Disclaimer: I was hosted in Dutchess County as a guest. My opinions, as always, remain my own.

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