The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY

City life can prove an obstacle between the rush and the retreat, especially as we begin riding the back-to-work momentum. It’s easy to yearn for those early summer days spent picnicking with a book or friend, watching the idle hours slip by. Perhaps it’s why I’m always looking for that perfect upstate getaway, a piece of land surrounded by trees to sweep away my worries. My time spent at The Olive Outpost, a 3-bedroom Airbnb set at the end of a private road just inside the border of Catskill Park in Olivebridge, NY, checked all my boxes for a relaxing stay in the woods.

Owned by partners Michael Pollak and Nick Cowan, the home was purchased after months of exploring various upstate towns to call their mountain escape. They landed on Olivebridge, a peaceful hamlet in Ulster County close to the charming towns of High Falls, Stone Ridge, and Accord, as well as the larger towns of Kingston and Saugerties. A series of serendipitous events, they said, eventually led them to discover The Olive Outpost, their saltbox-style home which now serves as a place to rejuvenate the spirit and connect with others. “Rather than purchase a box in the city, we sought a home in the woods,” says Michael, chief brand officer and co-founder of Heyday, a small chain of facial shops in the city. “It’s a great place to get away with a small group. We love coming here to socialize, cook food, maybe go on a hike. It’s much better than trying to squeeze in a quick drink at a crowded bar.”

Featuring whitewashed walls and floors, the Airbnb is a light-filled space inviting in the outdoors with large southern-facing windows. All three bedrooms evoke the spirit of camp lodging, but with modern amenities at your fingertips. Builders sourced the wooden ceiling and cross beams from nearby pines, and a local quarry provided the bluestone scattered outside. The majority of my time was spent lounging in the living room, watching deer pass through the nearby meadow. At night, near the edge of the trees, the lightning bugs created a band of flashing lights while coyotes howled in the distance. I couldn’t have imagined a better place to close my eyes, unwind, and put my feet up for a few days.

  • Location: Olivebridge, NY
  •  
  • Features:
    3 Bedrooms
    2 Full Bathrooms
    Radiant Heat in Floorboards
    Wood Burning Stove
    Outdoor Fire Pit
    Nearby Hiking Trails in Catskill Park
    Open Back Patio for Grilling and Sun Bathing
    Short Drive to Woodstock, Kingston, and other Catskill Gems

    Book Here

The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com

“Grilling on the porch while fireflies light up the meadow is one of my favorite activities,” says Michael.

The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com

A Room & Board sofa, positioned to keep watch on the meadow “completely takes you off the floor and into rest mode,” says Michael. “The challenge is staying awake.”

The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com

Vintage rugs were procured by local antique dealer Ron Sharkey, whose restored High Falls barn, The Black Barn, houses fabulous finds and occasionally hosts special pop-up events.

The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com
The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com
The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com
The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com
The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com

If you need to get some work done, there is no better place than the little table in the living room. Michael told me it was a vintage find, and I myself spent some dedicated time writing there.

The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com

Wallpaper by Chasing Paper was installed by Michael and Nick to create a cozy vibe in each of the three bedrooms.

The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com
The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com
The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com
The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com
The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com
The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com
The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com

“Each season here is incredibly special in its own way,” says Michael. “Fall is the most beautiful with crisp air and colorful foliage. Winter is wondrously clean with stark white landscapes. Spring starts muddy but then ends with budding potential, and summer is verdant, buzzing with life.”

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The Olive Outpost: A Tranquil Catskills Escape in Olivebridge, NY. andnorth.com

Although Olivebridge is tucked away in the Catskill wilds, a score of towns nearby make for a fun and exploratory day out, complete with gorgeous scenery, delicious dining options, and excellent shopping. Woodstock, with its quirky downtown strip, and Kingston, for those missing the city, are just a short drive away, in addition to the charming towns of High Falls, Stone Ridge, and Accord. Shoot over to Saugerties to visit the Farmers Market, landmark lighthouse, and the many boutiques, bookstores, and restaurants that line the streets.

EAT
Outdated, Phoenicia Diner, Olsen & Company

SHOP
Sweet Pea, Lovefield Vintage, Clove & Creek

EXPLORE
The Hudson Valley Garlic Festival, Saugerties Lighthouse, Westwind Orchard