May 6, 2025
Make Yourself at Home at The Owl Wine & Food Bar
Breezy Comfort at a New Preston Eatery
By Michelle Madden
Photos by Ryan Lavine
Perched on a hill in New Preston sits The Owl Wine & Food Bar, which happens to serve some of the best pizza in town—earning it Litchfield Magazine’s Reader’s Choice Award for Best Pizzeria. It’s a cozy local eatery that is elevated but casual, that welcomes you into its nest and makes you never want to leave.
Owner Ryan Cangello came from New York City in 2016, first as a weekender and then full time in 2020. He joined forces with John Bourdeau, who had begun The Owl, and then bought him out in 2023. Cangello’s overarching commitment is to create a place where everyone feels welcome. “I used to be in musical theater. The Owl is my stage, and everyone is on it with me. We are family here.”
Cangello grew up with a Lebanese mother and Italian father, where food was love. “Sundays I would pull up a chair and watch my mother cook. She would add fresh parsley to her manicotti—which was always my birthday-request meal.”
The heart of The Owl is a small room with an exposed stone wall, wooden beams, and a wine bar. A fire warms you in the winter, the rocky wall cools you in the summer. A distressed, diamond-patterned floor looks like it’s been walked on by country squires for hundreds of years. (The former home was built in 1870).
Extending from this nook is an inside-outside porch. The floor, with loosely inlaid stones, is reminiscent of an Italian hillside. A low stone wall secures the perimeter, and in the summer the breeze wafts through. At the top of the steps sits an expansive, shady patio where on summer evenings you’ll find Blood Orange Cosmos or Aunt Sassy Margaritas being sipped.
The Owl has polish without feeling fussy. The crockery has a fresh-from-the-kiln vibe; the wooden boards for the flat bread are crude and asymmetrical; the floors are weathered and worn. Tyler Juraska, the bartender, is tattooed and wears his turquoise hair with hipster confidence. With skinny black lamps dimly lighting every table, the mood is set.
Oh, and the food: It’s outstanding. The Cobb salad is light with a subtle truffle vinaigrette. The Bang Bang Cauliflower, with just enough heat, is a must-order. Your mouth will sink into the short rib sliders and never want to let go. The meatballs have just the right amount of garlic and—with a light tomato sauce and dollop of ricotta on top—closely resemble a savory cupcake. Order enough for everyone.
Though it’s not exclusively a pizzeria, there is a reason The Owl wins awards for its pies. The crust is thin, with black blisters from its time in the oven. The Bee Sting and the San Genarro are two of the most popular; the Emilia tastes like a summer garden.
Nothing is perfect about this place—and that’s what makes it perfect. When you come, leave your heels behind, but bring your dog. They’re family too.
The Owl is now open for Sunday brunch.—owlnewpreston.com
The Owl Wine & Food Bar, 18 East Shore Road, New Preston
