• Natalie Nicole Wilson

A Weekend in Dutchess County, NY

Updated: Mar 23, 2020

A cozy weekend getaway to Duchess County, uh yes pleaseee! ..Wait, where’s that?!


Being from the South, when I used to think of New York, I only thought about New York City. Upstate New York had never been a destination on my “list”. However, the beautiful farmland and the small towns that, as Ford says, give the south a run for their money, are not to be overlooked. You could get lost on the winding roads and beauty of northern New York. New York City IS great, but there is so much more to this state beyond the craziness of the city, and I’m so lucky I was able to get a little taste of its charm!


Ford took the reigns in planning this years VDay celebration. Shooting for a relaxing, romantic, do nothing but something kind of feel, this was just that. A weekend stay at Troutbeck Estate and Resort is good for anyone looking for a quick reset.

Where to stay: https://www.troutbeck.com/

Located in Amenia, New York, Troutbeck is a total experience. It’s an easy train ride for those living in the hustle of New York City and a scenic drive, for those, like us, living in Connecticut and surrounding areas. Recently updated in 2017, from a private estate to an award-winning hotel, they have perfectly preserved its historic charm while still giving a modern feel. Whether it's planted in front of one of the many fires places with a good book or exploring the cute surrounding towns, anyone could find contentment.


As always, Ford and I did a mixture of exploring and relaxing. We started our trip walking the precious town of Millerton, NY, which is about 10 miles from Amenia. A street of antique shops, a movie house and a diner, it’s definitely worth the visit. Oakhurst diner is a must. You feel like you are stepping back in time while enjoying classic and unique breakfast options.

Where to eat: https://www.oakhurstdinerny.com/

After our walk around Millerton, we checked into Troutbeck, grabbed a drink, and enjoyed a walk around the 240 acreage. Obviously closed for the season, they have a nice pool area with a cocktail bar and tennis court for their summer vacationers. For the winter goers, they have several spots and chairs around the property by the creeks to start a fire. It was chilly during our visit so we preferred the coziness of the indoors.


The interior is SO COOL. Winter or summer, I would be perfectly happy being inside. The numerous nooks, fireplaces, huge couches, bar area, dining space and pantry area is just awesome. At any moment during your visit, you can walk into their “pantry” and grab their daily choice of fresh pastries, sweets, and beverages for purchase. During your stay, try out the Troutbeck restaurant and wine selection, as well.

The area is full of options for outdoor exploring. Definitely more targeted towards the spring, summer, and fall seasons, you know Ford and I made due. We started our day off driving to the Walkway Over the Hudson located in Poughkeepsie, NY, about a 45-minute drive. At 212 feet above and 1.28 miles across the Hudson River, you can take in the beauty of the Catskill mountains. I definitely plan on returning next autumn for the fall foliage.

Where to visit: https://walkway.org/

From the Walkway Over the Hudson, we headed to Pine Hills, NY to hike to the Stissing Fire Tower. Again, totally not targeted towards the winter season, we made it work. Starting our hike from the Thompson Pond Preserve, there are two paths to the fire tower. The blue route is a tad bit longer but less steep, and the orange route is shorter but more challenging. We chose to take the orange route, confident in our hiking skills I suppose? The hike itself was challenging but complicated with tons of ice. But hey, the 360 panoramic views - WORTH the danger. We did take the blue route back and hysterically, that's when I busted ass.

Where to visit: http://stissingfiretower.org/

After working up an appetite, we ended our day at The Lantern Inn in Wassaic, NY, close to Troutbeck, for some beer, pizza, wings, and ramen. Ford enjoyed his pizza so much that he considered ordering one to go for later in the evening. Filled with the town's locals, the friendly staff and guests made us feel right at home. Their regulars are so regular that they have their drinks ready and prepared for them before they even walk through the door! I mean, who wouldn’t love that??


Where to eat: https://wassaiclanterninn.com/

In summary, if you are looking for relaxation at its finest with your lover, bestie, or fur baby (YES! Troutbeck is dog-friendly!), this is a spot for you. A lot of our trip was inspired by Escape Brooklyn, so make sure to check em out!


Next time you're planning a trip to the city, plan an extra couple of days to travel North, you won’t regret it.

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