Nestled in the hills of New York’s Sullivan County and the at the heart of the scenic Delaware River Valley, the MILK BARN is an extraordinary rental property just two and a half hours from New York City. The converted barn and its two guest houses, which sleep up to ten people, date back to 1873 and have passed through many hands over the ages–though traces of its past, both as a dairy barn and an artistic outlet, can still be seen today.

No doubt that much of the allure to this property is its fascinating history and aesthetic eccentricities. Before it was purchased by its current owners in 2015, the brunt of the barn’s conversion was done over a thirty year period, beginning in the mid-sixties and ending in the mid-nineties by a fashion photographer from New York City. The artist “escaped” nearly every weekend to work on the project, sleeping in the guest studio on the side of the house during conversion. As it progressed, he and his wife’s friends and colleagues joined the fun over the weekends, and the barn played host to photoshoots and infamously crazy parties that neighbors still remember today. (Side note: how cool is that?) The artist, who wished to remain anonymous, is responsible for most of the barn’s conversion and design; his aesthetic choices are clearly nostalgic for his Italian ancestry. The European influence can still be seen today all over the barn, especially in its more eccentric details–like the giant, tiled soaking tub in the basement, intricately etched window-doors between rooms, beautifully tiled marble floors, or the nude bas relief in the master bath. In the entrance, stained glass pocket doors open to a modern kitchen; behind them, a dramatic large wooden staircase makes every trip down the stairs feel like a grand entrance. In the open-format living room, the barn’s original enormous doors open up to a bluestone patio, connecting the inside and outside. Other notable features include three fireplaces, and a sauna with a built-in shower. It seems at every turn, there’s something new to discover–or Instagram! (Speaking of which, MILK BARN has a great Instagram account, too.)

Outside, the nostalgic Italian influence continues in the landscaping choice of cypress trees–though their tall, cone-like silhouettes look straight out of a Dr. Seuss book. A short walk from the barn, this guesthouse resembles a treehouse, perched several feet above the ground with wraparound windows. (Not to be confused with the actual treehouse, also on the property.) No bare bones here though–this tiny guesthouse comes with a fireplace! The second guesthouse, which hugs the barn, is a studio-like renovated shed where milk was stored before the days of air conditioning, and is equipped with a shower and sink. All three structures come with fifteen acres of back yard, including a private swimming pond.

All these great long-standing features at MILK BARN wouldn’t be nearly as special without its recent facelift, though. The interiors of the barn and its guesthouses were designed by owner Gabriel Adiv, who hand-picked its furniture and fixtures, which are a blend of vintage and contemporary, both found and custom. Perhaps the centerpiece of the whole house are the large table and benches, custom made by Jacob Ruch of Reason Modern in Red Hook, Brooklyn. The large table, easily seating our group of eight, played host to cocktails and conversation, breakfasts and dinners. Upstairs, each bedroom’s decor is simple yet thoughtful, with white-clad beds accented by Hudson Bay blankets. Other details throughtout the home like milk crates and cow skulls pay homage to the dairy farm it once was.

Looking past all the visual goodness here, even fragrances are part of the experience at MILK BARN–from Maison Louis Marie candles to the Palo Santo sticks which area readily available. Music and sound are big players too: a vintage sound system is complimented by an amazing vinyl selection, and guitars hang on many of the walls. Along with a clear understanding of what makes a memorable experience, Gabriel’s personality and passion for music really shines through.

Here at Escape Brooklyn, we know that properties as special as this are few and far between–it’s so rare to find such a unique home with so many amenities and with a fascinating history. That’s why you’ll find MILK BARN on Red Cottage Inc., a curated boutique rental agency with a focus on Upstate New York, whose roster features some of the most unique rentals in the region. A weekend rental at MILK BARN includes use of the studio, sleeping up to eight; visitors can also book the second guesthouse, sleeping an additional two, bringing the total accommodation tally up to ten people. Last, MILK BARN is also available for special events, such as weddings, photo shoots and recordings.

What To Do Around MILK BARN: Visit A Farm, Go Small-Town-Hopping, Visit the Site of Woodstock

Located in the Delaware River Valley, Hankins is a hamlet in the larger town of Fremont. Don’t be deceived by the word “town” though–it’s population was just 1,400 at the last count. The region is spattered with tiny little hamlets and towns to discover, the closest of which are Callicoon and North Branch, each about a 15 minute drive. If you’re visiting the MILK BARN, we’d recommend small-town-hopping in the area, where you can easily spend the day popping into antique and thrift stores, eating, drinking, and enjoying the outdoors. Starting in Callicoon, its river views, restaurants, and tiny shops create a quintessential river town vibe. Check out the IOU Thrift Store, or Callicoon Trading; for a rainy day, see a movie at Callicoon Theater, a historic movie theater that’s reminiscent of the “good old days” of film. Don’t miss the brewery, either!

Just a bit further south, Narrowsburg is another hip little town with great shopping like Nest, a beautiful home and lifestyle boutique; Maison Bergogne, an antique shop in an old car garage; and One Grand Books, where the stacks are determined by “desert island” picks from celebrities, authors and artists. Afterward, snag a seat on the patio for drinks or a meal at The Heron. In Livingston Manor, sign up for a farm tour at Apple Pond Farm to hold some adorable baby animals and learn about renewable energy and off-grid living; then stop in for lunch at Main Street Farm or The Arnold House.

For an outdoor adventure–or if you’re just looking for a great photo-op–head to Russell Brook Falls about 35 minutes from MILK BARN. Once you’ve reached the parking lot, the hard part is already over; the massive waterfall is just .1 miles into the trail. (Once you hear the falls, before you cross the bridge, veer off to the right for the trail heading to the sound of the waterfall.) On your way there or back, be sure to drive through the town of Roscoe, the fly-fishing capital of the United States. This “drinking town with a hunting problem”–or so say the tees at Prohibition Distillery–has no less than 6 hunting and fishing shops, and is also home to a brewery, fantastic handmade pasta, and lots and lots of fishing.

Last, MILK BARN is about 25 minutes to the site of Woodstock. (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 on-site is open from April to January.

Where to Eat & Drink Around MILK BARN: High-Brow Dining Meets Low-Brow Atmosphere–Eating in a Bowling Alley or A Gas Station

Though we mentioned a few restaurants above, there’s a couple more stand-outs that it’d be a crime not to mention. The big one not to miss is the newly opened North Branch Inn, just 15 minutes down the road from MILK BARN. This beautiful hotel, tavern and restaurant have caught the attention of The New York Times, Travel & Leisure, and more since its opening in September. The food is cooked by chef Erik Hill, previously of Hudson Clearwater in NYC and also the Arnold House. If bowling after your meal is half the fun here, then watching Erik prepare the food is the other half; the kitchen is totally open, and just steps away from the two-lane, hand-set bowling alley.

Another foodie hotspot in the area is the new location of Henning’s Local. This farm-to-table joint is in the most inconspicuous place possible: above a Mobil gas station. By description alone, we thought the restaurant would be small and cozy–but it’s actually quite large and loft-like. Reservations are recommended for this meat-heavy menu, but vegetarians might want to look elsewhere to dine.

Last, if you’re one of our long-time followers, you already know about our affinity for local, small-town dive bars… and this guide is no exception. Lucky for us, there’s a gem of a dive bar right down the road from MILK BARN, called McGurrin’s Pub, complete with darts, a juke box, and a great back yard with a barn. It’s the perfect place to begin or end your evening,–that is, if you can pull yourself away from the MILK BARN.

Escape Brooklyn thanks all of our wonderful friends who participated in our weekend at MILK BARN: Hat maker Tucker Shanley (whose awesome work can be seen in many of the photos above), Gillian Stippa of vintage clothier Steve’s Clothing, photographer Matt Rubin, Olivia Fleming of Olivia Kane Jewelry, Jeffrey Silversein of, and illustrator Sunny Erkerle