Like a lot of good things in the Catskills, The Outlier Inn began as one thing and grew into something else entirely. In 2002, artist and owner Josh Druckman traded the noise and pressure of New York City for a farmhouse and two acres in quiet Woodridge.
Since then, he has built out to 14 acres: seven year-round and five seasonal accommodations, indoor and outdoor showers, two full-service recording studios, a 100-seat amphitheater, a wood-fired cedar hot tub, a sauna and a spring-fed pond that turns a sauna session into something worth the walk.
“I’d like to say I had a vision when I started this place, but I didn’t. I just wanted a quiet place to make music.” – Josh Druckman
The farm runs on Merino sheep, Angora goats, alpacas, Oberhasli dairy goats, chickens, two cats and a notably kind dog named Beulah. They wander among three outdoor kitchens and an open-air table that seats 50.
What it is: An eclectic inn for individual stays, rejuvenating group retreat center, earthy event and location space with a world-class recording studio.
What it isn’t: A Jellystone Park. No pool, no cafeteria, no store stocked with candy, slingshots and squirt guns.
Where it’s at: About two hours from New York City at 307 Mountaindale Rd in quiet Woodridge, NY.
Solitude & Company
Once Druckman finished the original studio, he needed his music retreat to earn a living, so he opened it to other musicians. They needed somewhere to sleep. The neighboring property came up for sale and he bought it. Then he bought more. He repurposed the plots slowly, into a mix of lodging that reflects his personality, his love for good conversation and his faith in the beauty of simplicity.
Every option stands on its own, private enough to disappear into, open enough to pull you toward a shared kitchen or a campfire where someone is already sitting. A retreat within a retreat.
Four Seasons & Full Comforts
No two stays here repeat. Each year-round option comes with private bedrooms, a kitchen and bathroom, heat and air conditioning, a smart TV and the rest of the comforts you want from home.
The Main House: The Main House is a beautiful four-bedroom, two-bathroom farmhouse that sits at the heart of the Inn. It has a fully equipped kitchen with a Viking range, a dining room, living room, library and sunroom.
The Guest House: The Guest House is a year-round, two-family home located next to the Barn Shop. Guests can rent the entire home or choose a unit. Each has a separate entrance with private living spaces, private picnic table and charcoal grill.
The Cottage: The Cottage is a cozy two-bedroom with an eat-in kitchen, living room, bathroom and heat/AC. In addition to two full beds there are two queen sleeper sofas in the living room to accommodate up to 8 guests.
The Bungalow: The Bungalow is perfect for a small family with one bedroom and two very fun sleeping lofts, a full kitchen, bathroom and a private deck with dining table, picnic table and a grill.
Tiny House 1: Tiny House 1 is a rustic cabin made from locally hewn rough-cut lumber. It has a sleeping loft with a queen-size bed and a single-day bed, accommodating up to three guests. There is a full kitchen and bathroom as well as a deck with an outdoor dining table.
Tiny House 2: Tiny House 2 is a bright and modern home with an open plan, sleeping loft and queen size bed. There is a full kitchen and dining nook along with a full bathroom.
Open Air & Odd Angles
Here things get quirkier. Each one gives you somewhere to slip away to, and all of them share a communal outdoor kitchen, a covered dining area, restrooms and outdoor showers with hot water. Every one has outlets and Wi-Fi.
Tiny House 3: Tiny House 3 is cozy and bright, built from rough-hewn local pine and hemlock, with a sleeping loft, a full-size bed, a single day bed and a writing nook.
Tiny House 4: Tiny House 4 is built entirely out of recycled material and features a wall of windows that look out into the forest. In addition to a writing nook, it has a sleeping loft with full-size bed as well as a single day bed.
The Large Dome: The Large Dome is a magical 30-foot geodesic dome tucked into the woods with an open plan and big bay window that looks out over the spring-fed pond. There is one king-size bed and a sofa, but the dome can accommodate up to 15 guests, with additional guests bringing their own air mattresses, sleeping bags, and cots. It is a fun space for families and groups of friends who want a glamorous camping experience complete with colorful lights that turn the dome into a glowing bubble.
The Small Dome: The Small Dome is a beautiful 16-foot geodesic dome nestled into the forest on the far edge of the property with a queen size bed and sofa. There is Wi-Fi and A/C for the summer and heat for the early spring and fall. A private clawfoot tub with hot water sits outside, along with a picnic table, charcoal grill, firepit and hammock.
The Trailer: The Trailer is a gorgeous, fully restored 35-foot Spartan Spartanette from 1953. It has an open plan with one full-size bed, two twin beds, a beautiful banquette dining area, and kitchen with refrigerator and a sink.
“Staying here was a dream that made me feel completely at peace. It was so special I couldn’t post about it.” – Christina Moylan
Woodsmoke & Long Tables
Each lodging option gives visitors their own private experience, but this place turns on its third spaces* where people end up together. Kitchens work that way and there are three of them here: outdoors, lit, fully equipped, anchored by a wood-fired pizza oven and a long covered table.
Druckman may not have planned it, but his passion project nods to Sullivan County’s bungalow-colony history and the Borscht Belt heyday that produced it, when people came up here to slow down, settle in and share a summer of fewer complications.
“It certainly wasn’t intended, but by building this place in a way that encourages people to be together, it created the perfect environment for large group retreats. It made community come to life.” – Joshua Druckman
*A “third space” (or third place) is a social environment separate from your home (the first space) and your workplace or school (the second space).
Wool & Reverb
A stay here does not come with an agenda. No corporate soaps. No two spaces alike. No “what to do while you’re here” itinerary waiting at check-in. There is still plenty to fold into whatever plan you wander into.
The sheep, goats and alpacas grow wool. The chickens lay. Guests pitch in with chores if they want to. The organic garden stocks the Barn Shop, so you can grab a basket in the morning and carry it to dinner that night.
The fiber goes further than that. It pools with clip from other local micro-fiber farms to make a regional blend yarn that becomes hats, mittens and scarves, sold at the Barn Shop and at Fiber on Main in nearby Hurleyville.
The studio has hosted Yeasayer, Parquet Courts, Snail Mail and The War on Drugs, and anyone can book it. Bring a record you love, play it through that room and hear it the way you have never heard it.
Ashley Kossakowski, who fronts the Brooklyn band Groupie, spent a week here in August 2026, writing, cooking, walking her dog Roxy and laying down recordings. She came back because her first stay showed her what a week without distraction does to the work.
“I didn’t think about it until after the week was over, but Roxy and I never left the property while we were there and yet, it felt like we explored and experienced something new every day.” – Ashley Kossakowski
For Druckman, the happy accident keeps evolving. Much of it comes from the people who found The Outlier Inn and stayed friends for life. Much more will come from the people who have not found it yet.