3 cozy days in the Catskills and Hudson Valley

To New Yorkers like myself, everything outside the five boroughs is “upstate.” But to those who live in upstate New York, there are many regions. Even the most dedicated city-dweller sometimes needs the connection to nature, relaxation and a little escape that this vast region provides. That's why I recently spent a long weekend cruising around the Hudson Valley and into the Catskill Mountains. 

I feel like something of an expert because my boyfriend was born and raised in the Hudson Valley and has spent a lot of time taking me to his favorite local spots. Over our long weekend visit, we ate phenomenal food, per usual, vintage shopped, played in the snow, relaxed in the beautiful hotel and saw a show. 

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• When to arrive: Upstate New York is full of charming towns with quaint shops ⁠— but most are closed on Mondays and Tuesdays. To make the most of these towns, come on a Thursday or Friday. In warmer weather, expect an influx of city folks heading up for the weekend.

• How to get there: For those heading upstate, if you are going into the mountains, you should rent a car and drive up. If you plan to stay mostly along the Hudson River, Amtrak makes many stops along the way, and towns like Hudson are easily accessible on foot. For those flying in, the Albany airport is best to avoid long commute times post-flight.

• Getting around: One thing about making the most out of upstate is you will need a car. With roughly no public transportation and Uber a rarity outside of the larger cities (Kingston, Albany, etc.), expect to drive. 

• Where to stay: During our visit, we stayed at the oh-so-charming and dreamy Henson in Hensonville. The earliest record they have found of the building operating as a hotel dates back to a postcard from 1918 - The Hensonville Hotel. While it maintains good bones, it is also a designer's dream, with each room catching your eye.

• What to pack: Your packing list greatly depends on the season. This winter trip consisted of layers and boots for snow. But if you come in the warmer months, expect higher temperatures and humidity. 

Day 1

Morning: We left the city around 11 am and began our three-hour journey upstate. Luckily, my boyfriend has a car, so this was easy to navigate. The relief once you break out of the winding roads and chaos of Manhattan and find yourself on the NY State Thruway always comes with a calming exhale. 

Afternoon: Once we hit Poughkeepsie, we stopped at what may be my favorite deli in New York state: Rossi and Sons. This family-run spot is no frills and has fantastic food. I dream of their sandwiches. I prefer the Vittorio or The Number Four and always get it toasted. Be warned, the sandwiches are huge, and my boyfriend and I usually get one and split it. We always get our sandwiches to go, but there are a few tables outside if it is a nice day.

From there, we continued up to boutique inn The Henson. Located in the tiny hamlet of Hensonville, it is the perfect place to feel secluded and removed from the world, while still a 30-minute drive to shopping, winter sports and hiking. With no cell phone service and the ever-cozy atmosphere, you could it is a great escape. 

Evening: We started by heading down to the communal living room at the inn. The space is for all guests to use and loaded with games and a crackling fireplace. We enjoyed a glass of wine while I suffered a painful defeat at Battleship. 

Afterward, we popped over to the bar for a pre-dinner cocktail ⁠— an impeccable martini ⁠— before heading to their restaurant Matilda. The space is warm and inviting, with low-lit lighting, wood tables, it blends rustic with elegance masterfully. 

For dinner, we started with bread and butter and oysters, something I enjoy even more in the winter. This was followed by a potato, radish and turnip salad, reminiscent of classic potato salad, which I loved. We went on to split the striploin steak and Amish chicken.

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After dark: In this mountain town, don’t expect to find any wild nightlife, but there is always the hotel bar, or you can walk down to Zack’s Place. 

Day 2

Morning: We enjoyed a morning of sleeping in before heading down to the continental breakfast: think homemade jam, sausage, olive oil cake, feta and herbs, and freshly squeezed orange juice. If you want to venture out, Day June, a classic little diner down the road run by the same owners as The Henson, makes a delicious hearty breakfast. 

Afternoon: When it comes to upstate, there is truly so much to do. The afternoon is full of opportunities depending on your interests. For skiers, snowboarders, and tubers, head over to Hunter Mountain, which is only 10 minutes away. For shopping and a lively downtown, drive to Hudson. Along Warren Street, you’ll find trendy coffee shops like Moto, bookstores that also have a bar (Spotty Dog) and restaurants that will make you Swoon (the restaurant's name is Swoon, and it is fantastic). 

If you want to pick up some vintage clothing, make a visit to Five and Diamond or Proprietors Vintage and Handmade. Both have extensive and stunning collections. I find Five and Diamonds' pieces to be a tad more quirky, in the best way. 

If you feel like hiking (or leaf peeping, depending on the season). Overlook Mountain is a 4.6-mile loop that is rigorous and all uphill, but the view is spectacular. See the Hudson Valley like you have never seen it before. You’ll also walk past the crumbling structure of what was once supposed to be the Overlook Hotel but was never finished. Find stairs to nowhere and doorways into overgrown trees, it is hauntingly beautiful. Beware, bears and snakes do hang out in these parts. Hike with caution and, in snowy or icy conditions, bring spiked shoes. 

Evening: We went to one of our favorite restaurants in the town of Hudson, Feast & Floret, for dinner. The vibe is romantic, perfect for date night, and it is also home to by far my favorite Chicken Milanese, it is always so perfectly done (we have been five times). We also enjoyed the burrata, the meatballs, and a braised heritage pork pappardelle. The space is spectacular, filled with flowers that you can also purchase if you’re so inclined. I’ve had many beautiful nights here.

After dark: We bought a bottle of wine from Grapefruit Wine in Hudson and headed back to The Henson for a cozy night while it snowed outside.

Day 3

Morning: We began with the continental breakfast at the hotel once again, but if you are looking for something a bit more filling, check out the iconic Phoenicia Diner. It is a 30-minute drive, but the food is fantastic.

Afternoon: After checkout, we began the road trip back to the city. But first, we stopped in Kingston, another one of the Hudson Valley's most beloved towns. It is easy to enjoy a day here. Like its northern neighbor, Hudson, you’ll find streets lined with locally owned shops worth stopping in. 

Visit Everywhere Shop, a queer-owned stationary store where you’ll find stickers, trinkets and goodies galore. Then, walk over to Lovefield Vintage for denim and curated pieces to brighten up your wardrobe. Also on the street, you’ll find Rocket Number Nine Records to browse, as well as Capital Vintage, whose assortment of homeware and clothing makes it a must-visit. 

If you love an indie bookstore, head over to Rough Draft, which also has a bar in it (upstate loves that combo). Where Rough Draft is located you’ll find an interesting historic site at the fourway stop on the intersection of John and Crown streets, known as The Four Corners. On each corner the buildings were built pre-revolutionary war, the only one in the country. 

Evening: This evening, we were seeing the band Fleet Foxes at Ulster Performing Arts Center, a venue in Kingston, but first, we grabbed a drink at Stockade Tavern, home to one of the best Espresso martinis I’ve ever had. 

After a drink, we drove over to the darling Eliza, which is within walking distance from UPAC. Once a neighborhood pizza spot, Eliza, a European-style bistro, has managed to retain the charm of an old-school staple while creating inventive dishes and an outstanding atmosphere. The menu is always evolving, and the specials are great, but I love their grilled olives, grilled octopus, half chicken, and rigatoni. 

Following dinner, we went to UPAC and enjoyed the rest of our evening before the two-hour drive back to the city.

Chamidae Ford was a guest of The Henson. Lonely Planet does not accept freebies in exchange for positive coverage.