Elevate Dinner at These Westchester Restaurants With Rooftop Dining

The height of outdoor dining requires going a few floors up.

photo courtesy of Winston


Mount Kisco

The buzzy third-floor rooftop at Winston, with private bar, lounge-style seating, tables, and a balcony overlooking Mount Kisco, heats up with the weather, when the only thing cooler than the seasonal margaritas is the live music on Tuesday and Wednesday nights.



White Plains

No, it’s not open super late for the bar-hopping crowd, but Esposito’s rooftop is a laid-back first stop, with shaded pergolas, potted lemon trees, and two seating areas with firepits for sipping homemade limoncello.


freebird kitchen & bar

White Plains

Kick back with a frozen cocktail at this 100-person rooftop — the newest in the county — with a full bar, Southern specialties (like Nashville hot chicken), lots of seating, and views of Mamaroneck Ave.


Maggie Spillane’s

Mount Vernon

This spacious rooftop in Fleetwood is a popular warm-weather haunt with two full bars and more than a dozen flat-screen TVs for watching a Yankees or Mets game with a few beers and an order of wings.


Molly Spillane’s


From street level, you’d never know this spacious rooftop from the “Spillane’s” group even exists. But once inside and upstairs, the flowerbox-lined stone patio is utterly charming, with a large stone fireplace and bistro lights strung above the tables.


Savor at The Westchester

White Plains

A mall is an unexpected place to find a comfy-chic rooftop dining experience, but that’s exactly what The Westchester created when it debuted its renovated its food court in 2017, featuring an outdoor lounge with couches, a fireplace, and views of downtown White Plains.


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