Winter Snow

A Wonder-Filled Westchester Holiday

This itinerary captures all the enchantment of the holiday season, full of nostalgia and sweet treats, and capped by a dazzling display of lights that will fuel the sugar-plum dreams of youngsters and the young at heart. No little ones in tow? We’ve included options to “adultify” the weekend that add sophistication while losing none of the magic. 


Winter Wonderland entrance


Holiday Fair

untermeyer gardens



The fun begins in Armonk at Beascake Bakery, where Saturday morning means fresh mini donuts in a variety of creative flavors to go with your morning coffee.

After breakfast, stop by the Great Holiday Train Show at downtown Chappaqua’s historic Horace Greeley House, featuring a variety of vintage train sets running through festively decorated rooms. Then grab a healthy sandwich, salad or smoothie bowl at Bobo’s Cafe.

Dinner is at Chappaqua’s Le Jardin du Roi, a cozy, family-friendly French bistro serving classics like French onion soup, mussels and fries, and croque monsieur/madame, as well as a children’s menu.

For an electrifying end to your evening, hop in the car and head south to Kensico Dam Plaza for Westchester’s Winter Wonderland, a dazzling, 1.2-mile drive-through holiday light display.

You’ve all earned a good night’s sleep, so tuck the family in at a hotel in downtown White Plains, where accommodations range from the brand-new The Opus, Westchester to the Sonesta White Plains Downtown with an indoor pool that’s perfect for families. Or, opt for the Westchester Marriott in nearby Tarrytown—another family favorite for its indoor atrium pool.


Start your day in downtown White Plains with a quick bite at Hastings Tea & Coffee or a kid-friendly brunch at Freebird Kitchen. For a more sophisticated and eclectic brunch menu, try Lilly’s. All are just a short stroll from your next stop.

Fortified by your morning meal, bundle up for holiday shopping at the outdoor White Plains Holiday Market. With more than 60 artisanal vendors lining downtown Court Street, you’re sure to find the perfect gift for everyone on your list.

With your car trunk full and holiday dreams fulfilled, it’s time for one last treat before heading home: lunch at the White Plains location of Walter’s Hot Dogs, a Westchester institution.

A date-night Dickensian twist:

On Saturday after the vintage train show, shop downtown Chappaqua gems like the beloved independent bookstore, Scattered Books. Then point your car towards Tarrytown on the Hudson River for a late lunch/early dinner at the cozy Tarry Tavern. Catch the 5:30 performance of Mr. Dickens Tells a Christmas Carol at the Gothic-revival mansion Lyndhurst, all decked out in holiday finery. Then grab a hot Valrhona chocolate to go at Tarrytown’s Mint Premium Foods and take a stroll through Untermyer Gardens in Yonkers to experience the magic of The Grand Holiday Illumination.

On Sunday, cap off your shopping spree at Captain Lawrence Brewing Company with a seasonal brew in the beer garden.