Weekender 0

The Outlier Inn in Woodridge, NY

Part Airbnb, part farm, and part music studio, the Outlier Inn in Woodridge, NY is one of the most inspiring weekend getaways New York has to offer. Whether it’s the geodesic dome for a yoga retreat, or a tiny cabin to hunker down and write an album, each space is totally unique and designed to inspire the creative spirit. The unique and affordable accommodations make the Outlier Inn a magnet for artist and musician types—or folks that simply wish to get back to nature for a weekend. The shared spaces, such as the outdoor kitchen and the fire pit, create a sense of community between guests; you’re sure to leave Outlier with a few new friends. The creative retreat in the foothills of the Catskill Mountains, just 90 miles from New York City.

Owner Joshua Druckman moved to Woodridge to buy his first piece of land nearly 15 years ago. Originally from South Florida, he spent many childhood summers in the Sullivan County area of the Catskills with his grandparents. As an adult, Joshua moved to NYC for his music career, and returning to Sullivan County as a place to unplug from hectic city life. After eight years, he grew frustrated with the pressure and constraints of running a commercial recording studio in NYC, and uprooted for the Catskills.

“I bought my original farmhouse and 2 acres of land purely as my private home and music studio; a home base  to gather myself from the tumult of city life, and a place to plant roots in order to explore and discover myself,” Joshua told us. Over the years, he purchased adjacent land to his property, slowly expanding. “Working on the house, and on an electronic music album, kept me busy at first… Then a small parcel next door went up for sale with 3 dilapidated bungalows. I bought it and turned one of the bungalows into my music studio. I rehabbed another one as a two-bedroom rental, and the third sat decaying for many years—a perfect location for photo shoots! With the new studio and accommodations, I began to host musicians and bands who were looking for a retreat getaway. My idea was to share with others the inspiration that attracted me to the area and which I continue to draw upon daily.” Over the course of fifteen years, Joshua continued to buy more land, slowly repurposing the plots into more rental properties, recording studios, and even a small farm.

These days, Joshua has nine Airbnb properties available for guests to rent—but not for much longer. Next year, the Outlier Inn will refocus on catering to larger groups looking to rent either the “glamping” side of the property, or the entire thing. That includes nine structures on twelve acres, including a two-family guest house, two bedroom cottage, one bedroom bungalow, four bedrooms in the main house, two tiny houses, a geodesic dome and a Spartan trailer. Outlier Inn will be ideal for hosting large groups for events like yoga retreats, corporate getaways, weddings and large-scale photoshoots. So if you’re thinking about visiting, don’t hestitate!

During our visit, Denny and I stayed in the Spartan Trailer, which Josh bought at the nearby Tin Can Trading Post in Callicoon some years ago. Originally made in Tulsa, Oklahoma, Spartan trailers were considered the Cadillacs of trailers, and were created in repurposed WWII airplane factories. The massive, modern trailers were often used to provide returning soldiers with housing. When Joshua bought it, it needed some love, but it’s now in fantastic condition. It sleeps up to four people comfortably, in three beds. The kitchenette is especially cute, and amenities like electricity, an outdoor shower, shared kitchen make it a step above camping. The trailer starts at $175 a night on weekends.

We also stayed inside the Geo Dome, whose interior is very bare boned; a small stereo, shelf,  and blow-up mattress are the only furniture in sight. But the magic lies in waking up there, where you’ll watch the sun rise from your bed and listen as nature wakes up around you. It sleeps up to 30 people and is BYOB (bring your own bedding!) Its inspiration? Joshua grew up in South Florida, close to Epcot Center. “Ever since I was a kid, I was fascinated with domes, but never dreamt of owning one. But the opportunity arose, and I jumped on it. It sleeps up to 25 comfortably and is the perfect retreat spot, especially for yogis.” The geodesic dome rents for $450 a night on weekends, priced for six people. Additional guests are $25 per head.

Outlier Inn guests share an outdoor kitchen, outdoor shower/bath, outhouse, covered outdoor dining area, and if you’re lucky, a wood-fired hot tub. (Note: the wood-fired hot tub takes six hours to prep and is therefore available to large group rentals only!) Guests are encouraged to explore the property, which also includes a fiber farm with rabbits, sheep and goats who are all shorn for their wool. It’s then handspun into yarn and hand-crocheted into winter accessories by sustainable fashion designer, Ambika Conroy for her line Ambika Boutique. Highlights on the Outlier Farm include Cous Cous, the hilariously cute goat; and Andre the huge, marshmallow-like Angora rabbit. There’s also a farm stand, where guests can buy fresh organic produce, locally farmed meat, and other odds and ends. And though we’re providing a guide of things to do in the area, we’re betting you could easily spend the entire weekend without leaving the property. Bring a book to cozy up with on a hammock, make some elaborate meals in the outdoor kitchen, and get to know your neighbors at the nightly bonfire. We promise you’ll leave inspired.

What To Do Around Outlier Inn: Take In the Great Outdoors, Go For a Dip In a Local Swimming Hole, Visit the Site of Woodstock

The Outlier Inn is located between the Catskill Mountains and Shawangunk Ridge, both of which draw tourists from all over the world. The region offers a host of fantastic trails, picturesque farms, and scenic views that will literally take your breath away.

To spend a day outdoors, there’s multiple hikes nearby that range in time and difficulty. Starting with the longest and most difficult, a 25 minute drive to Cragsmoor will take you to Sam’s Point—which happens to be our favorite hike in New York State! The hike begins with a short trek up a big hill to an amazing lookout, and continues through a pygmy pine forest, then through blueberry fields, ice caves, birch forest, and ends with a waterfall. Though the entire hike will take you a solid four hours, with all the different stuff to see, time will fly. And if four hours sounds daunting, just know that much of the trail is flat, so it’s not super strenuous. Bring a picnic! For an easier and less time consuming option, head Neversink Unique Area, about a 15 minute drive from the Outlier Inn. A series of trails take you to Neversink River or to Katrina Falls, both of which are beautiful. These trails are shorter than Sam’s Point; plan on hiking for two hours. Last, there’s a 2.5 mile hike directly across the street from the Outlier Inn that skims the side of Silver Lake, leading into the town of Mountaindale. Ask Joshua, your Airbnb host, for more specifics. He can also make recommendations for the best information on swimming holes and fishing spots. (We prefer not to make that public info, though we promise they’re totally legit!)

Music lovers should take the 30 minutes scenic drive to Bethel Woods, the site of the 1969 Woodstock music festival. (No, Woodstock did not take place in Woodstock. In fact, Bethel and Woodstock are nearly 60 miles apart!) Park your car and wander the property at Bethel Woods Center for the Arts to see the field where the magic unfolded, along with the pond where festival-goers swam and bathed. The museum, which is fantastic, is on-site is open from April to January. After your visit, stop into Benji & Jake’s for delicious wood-fired pizza in their two-story restaurant (with two patios!) overlooking a lake. It’s scenic any time of the year, especially during the summer when it’s buzzing with boaters, jet-skis, stand up paddle boarders and kayakers.

Where To Eat and Drink Around the Outlier Inn: a Farm to Table Gem in Ellenville or a Newly Opened Gastropub in Hurleyville

The Hudson Valley and Catskills region are known for its food and farm to table restaurants. To taste some of the regions best offerings, head over to Aroma Thyme Bistro in Ellenville, which is a cute little town at the base of Shawangunk Ridge. It’s less than a 20 minute drive and the best option in the area for dinner. Though it’s offerings are on the pricier side, the food is very good and the restaurant is 100% certified “green”–the first of its kind in the Hudson Valley. (Insider tip: save $10 by joining their email list on their website!) Their bar is also awesome, stocked with 300+ craft beers, 300 wines and craft spirits, many of them local. If you’re doing the hike at Sam’s Point, be sure to hit this place for a post-hike meal! Another similar option for dinner is the Pickled Owl, a newly opened gastropub in Hurleyville, 15 minutes from the Outlier Inn. Highlights on the menu include their signature veggie burger, beer bread, fried chicken, and whole rainbow trout. Ask for a seat on their patio to soak in the outdoors.

Other options in the area include Pizza The Rock for a decent slice, or Italian sandwich–their eggplant parmesan is one of our favorites on-the-go! Just down the street, Brew is open seasonally and offers up tasty burgers and craft beer; we often stop here for lunch on the way further west in the Catskills. Just across the street, Dutch’s Tavern has more of an old-school vibe with similar pub-fare offerings. Last, guests can stock up on groceries in Rock Hill at the Trading Post, or in Woodridge at the IGA. (Just save your produce needs for local farms like Outlier, which you should check out first!)

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