Winter in Westchester 

By @ 12/31/19 in Art, Gay travel, Gay-Friendly, New York, Travel, Westchester

It’s a cold December morning and we’re only about forty minutes from the city, driving north along the winding I-87, but to the east, outside the frosted car window, is a different world: acres of farmland dusted with the first snow of the year, and farther out, a silver, sundrenched lake. Around the bend, we see whitechapel churches surrounded by dry streambeds and frozen sunflower stalks. And way out there, is a solitary farmhouse, small as a thimble, nestled in the snow.

Westchester County is a collection of small towns with big city sophistication. It attracts locals and folks who want the amenities of Manhattan without the rushed chaos of midtown life. And through the years, it’s caught the eye of A-listers like Jean-Georges Vongerichten, Richard Gere, and The Clintons.


For big shot city slickers, Westchester is an ideal long weekend, romantic getaway, or day trip. It’s where we go to unwind and unplugged without sacrificing the quality of food, art or service we’ve come to expect. Our most recent visit came with a revelation: Westchester is a foodie haven. And at the top of the list? Blue Hill at Stone Barns, a two-Michelin starred oasis of culinary and architectural brilliance (with a side of rustic charm.)

The restaurant is a venue that has hosted several queer weddings, as well. Tucked away in Pontatico Hills, Blue Hill is the star of Westchester and a destination dinner spot that gay boys make a special trip from the city to enjoy..

In Tarrytown, Goosefeather — a Cantonese hotspot inside an 1840s mansion — is garnering raves. The chef, Dale Talde, is something of a local celeb himself, having appeared as a contestant on Top Chef on two occasions. In 2019, his crab rice dish had the entire county in a frenzy, and why not? Jasmine rice, pickled jalapenos, generous amounts of locally caught crab with red and black tobiko has reimagined what we knew about Eastern cooking. 

And speaking of culinary celebs, Jean Georges himself is at the helm of The Inn at Pound Ridge, a charming getaway inside a rustic, two-story 1833 farmhouse with stone walls, wood floors, and cozy fireplaces. Jean Georges opened his upstate oasis nearly six years ago, where you can warm up with haute takes on comfort food perfect for winter nights: burgers, pastas, and wood-fired pizzas paired with local wines. 

For something a little easier on your bank account, check out a new favorite, The Little Drunken Chef


Opening in February 2020, The Abbey Inn & Spa in Peekskill is sure to be a new favorite for those looking to come to the country to be relaxed and revitalized. The inn has riverview suites, an onsite farm-to-table restaurant, and spa featuring treatment rooms, saunas and whirlpools. You can come to eat, sleep and be pampered in one of the most anticipated openings in the new year. 

Some years ago, three Westchester residents — Carey Lowell, Russell Hernandez, and actor Richard Gere, joined together to turn an old farmhouse into a rural but luxurious getaway called The Bedford Post Inn. Today, the Relais & Chateaux property is a charming boutique hotel, revered restaurant, and wellness retreat equipped with one of our favorite yoga studios. The Yoga Loft offers daily classes, workshops and private sessions to help you become a more centered, focused, and flexible you. 

 In Chappaqua, stay and dine at The Clinton’s favorite spot, The Crabtree Kittle House and Inn. The historic inn resides on a quaint, tree-lined street in rural upstate, perfect for especaping and regrouping in cozy quarters with one of the best restaurants in town (you can even reserve The Clinton’s favorite table!)


Westchester County is brimming with art, with top-notch museums, performing arts, and events. The Hudson Valley MOCA in Peekskill is our favorite, with contemporary artists and edgy works that challenge and enthrall visitors. And the new Sing Sing Prison Museum is set to be as controversial as it is educational, telling its story for the first time through tours, archived photographs, and films. 

If you’re looking to see a show this winter, check out Almost Queen — a cover band tribute to Freddy Mercury — at Port Chester’s Capitol Theatre on February 1st. We’ve also got our eyes on the Calexico and Iron & Wine show on February 5th, or the return of the elusive Lauryn Hill on February 20. At the Emelin Theater in Mamaroneck, Lisa Loeb performs on March 21. 
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