A Guide To Upstate New York, Everyone’s Favorite Escape From The City

Getty Image

When you live and work in New York City, you’re sapped by the end of the week. The frenetic energy of the city is exhilarating in doses, but if you don’t take the time to slow down and get some fresh air, the Gotham circus can really wear you down and soot your spirits. For this reason, I’m a huge advocate of getting the hell out of the city. As far away as you can drive, until the buildings are sparse and low, the sky is in full view, the air smells un-toxic, and the sounds of ambulances and car horns are a distant nightmare.

For more than a century, artists and writers have been drawn to the serene wild of the upper Hudson Valley, the Berkshires, and Vermont. The time that they spent there in the mid 1800s and early 1900s infused the rugged and raw space with culture and significance. The birth of the Hudson River School of American Landscape Painters plus the success of novels and paintings from the region turned upstate NY into a much buzzed vacation hotspot. With elevations reaching over 4,000 feet and hundreds of state-regulated trails and points of interest, it’s an idyllic contrast to the chaos of the city only two hours south.

By the mid 1900s, the Catskills were already considered a resort destination. It was an inexpensive place for working class families to vacation, for white collar families to buy land, and for immigrants to establish their own micro communities.

By the time the Woodstock festival rolled around, upstate New York had something up there for everyone. Then, as the century neared an end and transportation became more efficient and vacation towns began to pop up like acne all over the East Coast, the Catskills and surrounding cities began to suffer. Only now, in the last decade, is the area seeing a newfound interest from city dwellers. Dubbed a satellite community for Brooklyn folk, the upstate region is now thriving again. With restaurants that rival NYC standards and boutique lodges that out-style the chicest European mountain chalets, upstate New York is once again the place for artists to and creatives to split from the metropolis.

Here’s your guide to the new Upstate with a capital U — where to eat, where to sleep, what to do and where to go if you bump into your boss at a farmer’s market.

Where to go that you’ll feel OK with no cell service.

The Spruceton Inn looks like a motel because, once upon a time, it was. But don’t judge a building by its exterior. Gutted, updated, and redecorated by a minimalist with an eye for rustic retro-chic, The Spruceton offers modern comfort situated in an open wild. Literally in the middle of nowhere, with no WiFi in the rooms, this is the place to go to unplug and wake up with the sun. You won’t find a single distraction here besides the views from your giant window, so it’s perfect if you want to finish a book or just hear yourself think.

Don’t panic, there’s a bar onsite with WiFi and you’re only 30 minutes from civilization if the sound of birds and breeze becomes too real for you.

Where to hike, or er, take a great Instagram.

View this post on Instagram

cave problems

A post shared by Kaitlyn Wylde (@birdiewylde) on

Sam’s Point Preserve is a great place to go if you want views, a workout, and some out-of-the ordinary sights. It’s part of the Minnewaska State Park Preserve which is one of New York’s most breathtaking and diverse parks. Sam’s Point is located at the highest section of the Shawangunk Mountains, making for epic views. There are ice caves, waterfalls, lakes, rock scrambles, and both five mile and eight mile trail options.

It’s impossible to leave this park without an impressive Instagram, if you’re into that sort of thing.

Where to eat so much you cancel your hiking plans.

View this post on Instagram

Brunch is our favorite 📸 @xtine_ehly

A post shared by Prospect Restaurant (@scribnersprospect) on

Scribner’s Catskill Lodge gets a lot of attention for their accommodations. Their rooms are huge, their beds are cozy sinkholes, their decor is an Insta-dream and their views of Hunter Mountain are unparalleled — seeing as the lodge is literally across the street from the mountain. I get why people come here over and over again, treating it like a weekend timeshare, but my love for the lodge is actually rooted in the kitchen. Their new restaurant, Prospect, is on par with New York City’s most celebrated eateries. I can say this with confidence, because I’ve eaten there so many times that I’ve literally had everything on the menu.

Country brunch is ace, Apres ski drinks are worth a slow clap, and dinner is a home run. You don’t need to read the fine print to know that the food is local. The fresh snap of the veggies, the rich chew of the meat, unprocessed elegance of the cheeses say it all. You’ll make plans to hike in the morning to burn off some of your dinner, but instead you’ll sleep in and head to brunch in your sweatpants, because they’re all that fits you now.

Where to get your culture on.

Perched atop the highest residential peak in the upper Hudson Valley is Olana, a NY State Historical Site and onetime home to 19th century famed landscape painter Frederic Church. A centrical force of the Hudson River School for American Landscape Painters, Church did quite well for himself. He left behind a perfectly preserved mansion that overlooks all of upstate New York. With hundreds of original and extraordinarily valuable pieces of art hung on its walls, this estate is a must see. A tour will cost you about $8 and you’ll get an hour of incredible peeping.

You can hang on the property and go for a walk or take in the views from a bench. Even if you don’t know about Church’s work, you’ll find something to love about this experience.

Where to go to feel like rustic royalty.

The Windam Hill Inn is not just nice, it’s perfect. It’s only after my short stay there that I felt I understood hospitality — what it ought to be. The location is remote, and gorgeous. The Inn sits on over 100 acres of land, both manicured and wild. Without the excellence of its staff, the Inn still wouldn’t have to try hard to be alluring. The building is charming and old, with roaring fireplaces around every corner. The floors are original and creak under runners. It’s cozy, it’s grand, it feels like someone else’s home and yet… open and welcoming.

Finding an old inn in Vermont is not difficult but the fine people who run this inn are one in a trillion. During my stay, I learned that hospitality is anticipating your guest’s every move and making sure that it’s smooth. It’s delighting your guests at every possible opportunity. At the Windham Hill Inn, you have a helping hand waiting for you just as you begin to look for it.

Okay, so NBD, they cleared the snow off my car every few hours and brought me fresh baked cookies and local cheeses while I read in the living room. They went above and beyond and with a grace that I didn’t know to expect from a modest old house on a hill in the middle of nowhere. Still, when I sat down in their dining room for dinner, I had meager expectations. The chef was local. She wasn’t of NYC Zagat pedigree. So when I tell you that it was one of the most gourmet, fine-tuned, fresh, rich, and decadent dinners I’ve had in my life, know that it’s true. But don’t take my word for it, go to the Winham Hill Inn with average expectations and enjoy having your mind blown as you feel like a member of the royal family the second you walk in.

And then leave with the disappointment that no one is going to fluff your pillow or feed you oven-fresh scones for a mid morning snack back home.

Where to go to get it on.

View this post on Instagram

the great indoors 🌲

A post shared by Kaitlyn Wylde (@birdiewylde) on

The FoxFire Inn is beautiful, and upon entry you’ll decide you want to get married there or move in or take a picture of everything. Originally used as a boarding house in 1914, the building was renovated in 2013 and got to keep much of its original charm. Owners Eliza Clark and Tim Trojian certainly put a lot of work into making every inch of the property look like it belongs in a Vogue editorial. Antique furniture, sheepskin throws, antlers, pharmacy lamps, original stone fireplaces and upholstered chairs that you thought only existed in 14th century paintings are scattered throughout the communal areas. Between the wine selection, record player, and the pool-sized soaking tub, I dare you not to feel sexy here.

Where to fall asleep to the sound of a babbling brook.

Sheffield, Massachusetts is a part of the Berkshires that’s so chill, you’ll think everyone’s high. And they probably are. Snug at the foot of Race Mountain and Race Brook is Race Brook Lodge, a no-frill country inn that has everything you need. Peace, quiet, a locally sourced and award winning restaurant and bar, enough board games and rare books to entertain you for a long weekend and immediate access to some incredible nature activities. If you’ve never fallen asleep to the sound of a babbling brook, I highly recommend it. It’s beyond the lulling ability of any Sharper Image noise machine and will make you feel like you’re a million miles from home, in the best way.

Where to go if you just dodged your boss at the Woodstock Farmer’s Market.

View this post on Instagram

High time for a Sunday Soak. 🛁 📸: @emma_austen

A post shared by Hasbrouck House (@hasbrouckhouseny) on

Okay, so you thought you were far enough away from the city to bump into anyone you know. But you were wrong. Upstate is so popular that you’re actually bound to bump into someone you know, if you spend time in the super trendy spots like Woodstock or Phoenicia. If you were at the farmers market and you totally saw your boss in knee socks and sandals, but he didn’t see you, you still have time to turn around and have a great weekend that feels like a getaway. Head back down on 87 towards a town called Stone Ridge. First of all, it’s adorable. It’s one of those towns that has one bar, one grocery store and seven churches. It also has an inn called the Hasbrouck House which is gorgeous and surprisingly luxe — sure to be your savior and oasis. At the house you’ll find guest rooms that have cooler furniture than any of your antique Pinterst boards, an impressive restaurant called Butterfield, an enormous pool, lake, 100 acre apple orchard, hiking trails and bon fire stations that are lit nightly.

Plus, it’s right around the corner from Minnewaka State Park so if you want to get your adventure in, it’s simple. But if you want to stay inside and enjoy the clawfoot tubs, and fancy smelling Kiels bath products while you hide from all things work or effort related, no one will blame you.

Where to go if you want to play with a baby lamb and wonder why the hell you live in the city.

View this post on Instagram

you're all i ever wanted

A post shared by Kaitlyn Wylde (@birdiewylde) on

Bovina, New York. You’ve probably never heard of it because it’s in the middle of no where and at least three hours from NYC and without many luxe accommodations that NYCers are looking for when they commit to such a drive. This small town is made of sprawling fields and endless farms speckled with livestock. It’s also got two restaurants (Brushland Eating House and Table on Ten) that are so popular and renowned that most NYC foodies have made the drive just to taste their menus. But most importantly, if you love baby lambs, is the Green Shepard Farm, which is a small family run business that raises flocks of Finnsheep.

They also offer a portion of their land up for camping grounds for only $35/night so that you can sleep under the stars and next to a bunch of baby lambs (if you go in the spring). If you’re lucky you might even get to play with them.

Where to go to find your friends.

View this post on Instagram

Speaking of family supper…🍝

A post shared by GASKINS – Germantown, NY (@gaskinsny) on

Hudson, New York is well on its way to becoming a foil to Brooklyn, New York. The once not-so-safe town has turned into a slightly-safe town that’s confusingly over-run by high end antique stores and bars that serve $14 Negroni’s. Sound familiar? Yes, Hudson really is a lot like Brooklyn. Which is exactly why the Brooklynites are making the weekend pilgrimage. If you’re looking to get out of the city to get a dose of nature, but don’t want to lose cell service, Hudson is your town. With epic views of the Catskill mountains, sprawling farmland, and a diverse and bougie town center, you’ll easily check off all of your boxes.

The best place to eat is called Gaskin’s and it’s actually just outside of Hudson in Germantown. I got there at 5 p.m. on a Saturday and had to wait for a table. You won’t realize how ironic this is until you pass 50 miles of farmland and broken tractors to get there. As you sink your teeth into some homemade pasta or farmer’s bounty style salad, you’ll think “Zagat,” and you’ll be right. Gaskins is the brain child of Nick & Sarah Suarez — you might remember them from Diner, Marlow & Sons, Romans, Franny’s, Gramercy Tavern or The Modern – you know, some of New York’s finest and highest regarded eating establishments? When you’re looking for a place to lay your head and your overstuffed stomach, you’ll probably be allured by one of the many Upstate chic inns like Rivertown Lodge or The Hudson Milliner, but the combination of their lack of availability and your wallet might lead you elsewhere.

I stayed at 26 Warren Bed & Breakfast. It’s right in the middle of town in an old federal building and it’s run by a Jamaican healer who’s so charming and buoyant you’ll want to become best friends. The inn is affordable, clean and artsy. The host makes a three course breakfast in the morning that you’ll eat in his living room with about eight other people who are heading back to Brooklyn too. After you all photograph the slow pooling of pre-pierced egg yolks, maybe you can arrange a carpool — in which you will all lament the impending and ominous goings on of the NYC Monday ahead.