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If anybody knows what cool is, it’s Tracey Ryans. The entrepreneur, marketing strategist, and restaurateur appeared along with Malcolm Gladwell, James Corden, and Ice Cube to discuss the meaning of “cool” on the 2018 MSNBC documentary miniseries The Story of Cool. As a partner behind New York’s biggest hot spots, like upscale Mexican restaurant La Esquina, Caribbean hangout Miss Lily’s, and cinephile favorite Metrograph Theater, Tracey Ryans knows just what it takes to attract the scenesters, models, celebrities, and creatives who frequent these venues. Through his business, Tracey Ryans Agency, he has also served as a consultant, revamping Soho House New York, and collaborating with Serge Becker on The Box and Volume.

Fifteen years ago, Ryans found himself drawn away from the glamour and the velvet ropes of the Big Apple to the bucolic town of Rhinebeck in upstate New York. There, he partnered with Michael DeCola to convert the historic Grasmere Farm—a 500-acre property comprised of two buildings built in the early 1700s, and a barn house that was once the estate of former vice president and New York governor Levi P. Morton—into an event space that can be booked for weddings and parties. It was the right time for Ryans, who longed for an existence away from the hustle and bustle of the big city. “It’s one of those things, as you get older, you want more space, you want more quiet, and my business partner grew up here, so I had it this way and never looked back,” he says. “I plan on being here forever.”

Being surrounded by nature is nothing new for Ryans, who grew up in a similar environment in western Massachusetts near the Berkshires. Although Ryans still has a home in Brooklyn’s Park Slope, Rhinebeck offers him something he can’t get in the city. “Up here, being able to walk in the middle of the woods, bright and early, and being able to find a rock to sit on in the middle of the woods, it’s just perfect,” says Ryans. “It puts you in that place, recharges the battery, gives you all the energy you need to go back in the city and do what we do.” Ryan is currently working with Taylor Baker on Cortina Vallery, a 300-acre private ski resort located in Hunter, New York, a picturesque destination in both the summer and winter.

Document—Describe your perfect day in the Hudson Valley.

Tracey—6am Dharma meditation walks through the forest, watching the sunrise through the mist and the trees, sailing on the Hudson River with my friend Sergia Rebraca then drinking whiskey sitting by an open fire and singing along to Lead Belly with Jon Mensch, Michael Decola, Manolo Campion, and Jon Berry.

Document—What’s your most inspiring season upstate?

Tracey—Every season is perfect upstate.

Document—What is the first place you can’t wait to take friends?

Tracey—To the waterfall house at Grasmere and Liberty Public House.

Document—Are you more of a city person or a small-town? Has that changed over time?

Tracey—I love the city but consider the train ride upstate to be my spiritual car wash.

Document—Where do you go to get inspired, think, and decompress?

Tracey—There’s nowhere to go but inside. I find that place through my daily mindfulness practice.

Document—What music do you like to listen to while upstate? What songs remind you of the Hudson Valley?

Tracey—Lion Babe, Crash for the People, Siimba Selassiie, Hailie Supreme, and Steely Dan.

Document—What do you consider to be Hudson Valley required reading?

Tracey—The Hidden Life of Trees by Peter Wohlleben and Why We Sleep and Dreams by C.G. Jung.

Document—Is there a person in your life you wish could accompany you here?

Tracey—Cecile Barendsma, my wife.

Document—Where are the best places to hike, stargaze, or get into nature?

Tracey—We purchased a private ski resort in Hunter, New York called Cortina Valley Ski Resort. It’s a beautiful place to stargaze and hike in the summer.

Document—How do you feel when you return upstate after being away?

Tracey—Like a butterfly folding back into its cocoon.

Hair and Grooming Mimi Quiquine at She Likes Cutie. Editor Austin Bailey. Sound Greg Francis. Color Oliver Eid. Photo Assistant Annabelle Snoxall. Production Liana Blum and Patch Ward.