Weekend Getaways From NYC: A Perfect Weekend In Upstate New York

Sometimes the best part of living in New York City is taking weekend getaways from NYC with friends. Well, only 90 minutes from Manhattan and Brooklyn is a place with such natural beauty you’ll think you’re in Iceland or Hawaii. In fact, you’re less than 100 miles from the concrete jungle of the city. This natural paradise is located in upstate New York, the Catskills, or if you want to be precise about it, Sullivan County, NY. It’s seriously one of the most serene places you’ll ever visit.

Skeptical that something so pristine could exist so close to Manhattan? It’s true! Below is a chronicle of my weekend getaway in upstate New York, staying at the Hillside Schoolhouse, a New York state recognized historical landmark, with my boyfriend and another couple.

Built in 1892 and recently renovated with five-star amenities that modernize it while preserving its historical charm, the Hillside Schoolhouse doesn’t disappoint. The writer Washington Irving called the Catskills “a spellbound region” and you’ll see exactly how my trip lived up to all the hype in the coming paragraphs.

So here it is, the story of my weekend getaway from NYC with the love of my life and some friends, into the wild woods of Sullivan County and upstate New York.

Of all the best weekend getaways from NYC, the Hillside Schoolhouse is the best in the Catskills of upstate New York.

The Hawk's Nest in New York

Friday: The Upstate New York adventure begins

1:00pm — Arrive at Port Jervis, NY

My boyfriend and I convince our friends to call in a vacation day so we can all leave NYC at 11:00am, avoiding rush hour traffic.

Our first stop is Port Jervis, an historic railroad town in upstate New York filled with architectural gems. The main street in town is peppered with antique shops, yoga studios, bars, restaurants, and parks.

For lunch, we eat at a vegan comfort food restaurant, Fogwood and Fig. Then we wash down our meal with a cold beer at Fox N’Hare brewery, a craft brewery that specializes in beer made with New York hops. Afterwards, we walk down Front Street to explore all of the other amazing things to do in Port Jervis. We’re particularly excited about popping into all of the antique shops, each with its unique character and offerings.

Then we’re back on the road, headed towards our weekend getaway paradise. Once we leave Port Jervis, we find ourselves on the the Upper Delaware Scenic Byway, which was voted by USA Today as one of the most beautiful drives in the United States for its “breathtaking vistas.” As you can see from the photo, the views of the Catskills from the winding road are truly breathtaking. Along the drive to our final destination, we find some other photo-friendly lookout points, thoroughly enjoying the leisurely ride to our upstate Airbnb.

3:00pm — Luxury hotels in upstate NY? We’re there

Weekend Getaways from NYC

After the joy ride along the Upper Delaware Scenic Byway, we arrive at our upstate New York destination, the Hillside Schoolhouse, which is tucked on a quiet Catskills street. The house is marked with a historic sign detailing its past life as a schoolhouse in the 1800s and later in the 1900s as a church. Before we even enter the house, we’re in love with the historic charm of the Hillside Schoolhouse. We can’t believe how tall the schoolhouse is and how magical it appears, sitting on top of the hill, like something out of a chic fairytale.

4:00pm — Take in the best Airbnb in New York

Upstate New York

We soak in the house, amazed. Everything is spectacular! One of the designers of the house, Bronson Bigelow, said it best in an interview: “I am in awe every time I walk into the Schoolhouse. Many guests have said that the Schoolhouse feels like staying in a magazine.” That’s exactly how we feel.

It’s so cool, it doesn’t even feel real. The ceilings are at least 18 feet high, the couches are expansive yet cozy, and every little detail shines with a specific mix of country charm and magical warmth. Fun Fact: The chalkboards gracing the walls of the grand living room area are the schoolhouse’s original chalkboards. Plus, the main entrance still has its original stained-glass in tact. Looking up towards the celling in the guest bedroom for the very first time, we can’t believe our eyes! What do we see? The original schoolhouse cast iron school bell, hanging snugly as it did over a century ago.

6:00pm — Explore Narrowsburg, NY

Narrowsburg, NY

We head to the river town of Narrowsburg, which is about a 20-minute drive from the Hillside Schoolhouse. There are so many things to do in Narrowsburg. We sightsee. We explore. We shop. We eat.

On the shopping front, I buy a book at One Grand Books, a bookstore where each shelf is curated by a different artist or celebrity. So, for instance, the shelf from which I selected my book, The Driver’s Seat by Muriel Spark, was curated by Tilda Swinton and features her ten favorite books. Some others who have curated shelves: Roxane Gay, Michael Stipe, Chelsea Handler, Lena Dunham, and more. It’s one of the most original ideas for a bookstore I’ve ever encountered. I love perusing a bookstore organized according to what some of my favorite icons love to read. I also pickup a trinket from Maison Bergogne, an antique shop run by a French artist out of an abandoned school bus parking lot. Be careful when you enter this store because you could easily get sucked into spending the entire night night exploring it.

Now, it’s dinner time. We opt to eat at at The Laundrette, a gourmet restaurant specializing in salads and pizza that has enormous windows overlooking the Delaware River. The food is as good as the views are, and the service is impeccable at The Launderette. Another popular (and delicious) spot in Narrowsburg is the Heron, which we can’t wait to try the next time we’re in upstate New York.

9:00pm — Fall asleep under the New York stars

Hillside Schoolhouse Star Gazing

We go to bed early because country living and weekend getaways are all about rejuvenation. Plus, we have a big day of adventures planned for the following day!

Yet, the night holds one more surprise for us. My boyfriend and I lay down in the master bedroom’s comfy bed only to realize that the skylight above is perfectly placed. Our view of the night sky above, with its millions of twinkling stars, is absolutely breathtaking. There seems to be no light pollution and the scene is so magical we spend at least 30 minutes just stargazing from the comfort of our bed. This is definitely something you won’t see in New York City! And perhaps the most romantic way to fall asleep ever.

Upstate getaways

Saturday: The weekend getaway continues!

10:00am — Espresso in bed

coffee in bed

The Hillside Schoolhouse kitchen is fully equipped with everything you need to cook a great meal, and, more importantly (to me, at least), everything you need to prepare a great cup of coffee. We make a light breakfast of pancakes, fruit, and coffee to eat from bed. As for our morning caffeine fix, there’s an espresso machine that instantly oozes one of the best cups of coffee I remember having in a long time. Maybe it wasn’t just the coffee, though; maybe it was the combination of the coffee, the scenery, and the privilege of staying at the best Airbnb in New York that made everything so wonderful. The whole house was illuminated in warm morning light that made us feel airy and happy. This is how Saturday mornings were meant to be enjoyed—in a state of complete relaxation amidst the wonders of natural beauty.

11:00am — Barryville Farmers’ Market

Farmer's Market in Upstate New York

What weekend country getaway would be complete without a visit to a farmers’ market? The Barryville Farmers’ Market is open every Saturday, from late May to late October, and it’s only a five-minute drive from the Hillside Schoolhouse.

The market is full of organic produce, artisanal goods, and other treats. Everything is sourced locally, mainly from New York, though a few vendors come from across the Delaware River in Pennsylvania, which is just a stone’s throw away from Barryville. We procure fresh meat from Hilly Acres Farm, vegetables from Beaver Dam Brook Farm, and bread that was baked just earlier that morning from Myrtle Avenue Bakehouse, among other things. A quick tip for city folks: The Barryville Farmers’ Market isn’t your Union Square NYC farmer’s market. Credit cards aren’t accepted by most vendors, so be sure to bring cash with you! If you forget (like I did), don’t worry too much. You can get cash at the River Market right next door, where there’s an ATM.

1:00pm Find swimming holes in NY and the Delaware River

Swimming Holes in NY

There are so many picturesque swimming holes in NY and the water in the Delaware River is so pure and refreshing. Our friends want to go on an adventure, but my boyfriend and I are craving a more peaceful day by the water.

My boyfriend and I (aka Team Relax) head to Skinner Falls for a day of sunbathing and swimming. Skinner Falls is so majestic that I feel like I’m transported to Neverland as soon as we arrive. It’s hard to describe in words what Mother Nature managed to accomplish here. Essentially, there are various rock formations in the Delaware River forming a series of naturally occurring miniature pools enclosed by rocks. You can sit in these pools and allow the river to massage you, or just set up a towel and sunbathe on a rock as the river rushes by, creating a pleasant background noise.

While we were at Skinner Falls, our friends chose to go rafting down the Delaware River on a large float. They rented the raft and paddles in Barryville for the 8-mile journey down the river. Throughout their trip, they spotted various birds and other wildlife. They also stopped at several points along the river to swim and picnic.

6:00pm — Prepare a farm-to-table Catskills dinner

Farm to table dinner

Back at the Hillside Schoolhouse, we prepare the perfect upstate dinner using all of the food we collected earlier at the farmers’ market. We follow a special recipe from Field Guide to the Hudson and Upper Delaware, by Laura Silverman, a naturalist and the founder of the Outside Institute. In addition to the delicious recipes, within the guide we learn about the local ingredients we’re using, including some medicinal applications for plants in the region. Before dinner, we munch on snacks outside in the early evening. We enjoy our main meal—a veritable feast of healthy, local produce and meats—in the massive dining area indoors.

8:00pm — Cocktails at the Bang Bang Bar

Cocktails at the Bang Bang room in Barryville, NY

Following dinner, we drive to the Bang Bang Bar, where they serve only beer, wine, and spirits made in New York state. The scene at the Bang Bang Bar feels very Manhattan-meets-upstate, and the cocktails are as good as anything in the city. The difference is that everyone seems so much more relaxed at Bang Bang, the effect of drinking beneath a clear, star-lit sky, surrounded by rushing brooks. We meet some new friends as we enjoy a night out in the country.

If you’re trying to find the Bang Bang Bar on Google Maps, however, beware! You won’t be able to find it that way. The site isn’t listed. As a loophole, input the Stickett Inn in Barryville and follow the directions there. You can’t miss the Bang Bang Bar. Cheers!

Weekend Getaways

Sunday: Exploring the Catskills

Sunday, 9:00am — Find the best hiking trails in NY

The Catskills

The only problem with hiking in the Catskills is how many options there are. The region has so many hiking trails that it would take years to hike every single trail. We ask our Airbnb host for a few recommendations and receive a plethora of hiking suggestions immediately.

Since we can’t decide on what the best hike is, we decide on two separate hikes. First, we hike the Mongaup Trail, which is about a 20-minute drive from the Schoolhouse. We choose this hike because it allows us to walk with the river by our side the whole time. Next, we tackle the Tusten Trail, which is much closer to the schoolhouse. We hike the Tusten Trail because this hike has an incredible elevation and when we reach the uppermost point of the hike, we can see the entire Delaware Valley.

3:00pm — A pitstop in Warwick, New York

Upstate New York: Warwick

Before heading back into NYC, we can’t help making one last stop. We pull off the main road and head into Warwick to pop by the Warwick Inn for a leisurely late afternoon lunch. Sitting outside at a table on the quaint wraparound porch, we marvel at the awesomeness of the previous 48 hours. What a pleasurable trip we’ve had! And what a convenient getaway from NYC we’ve discovered. Breathing in the last few gasps of delicious country air, we start planning our next visit.

About the author

Mélanie Berliet

I adore the following, in no particular order: knee-high tube socks, acrostic poetry, and my little brother. Click here to learn more!