The Winter Show Returns! See Inside the Annual Opening Night Celebration

On Thursday evening, The Winter Show’s Opening Night preview once again proved that what’s old is new again, and that the world of antiques is anything but staid. The event drew a stylish crowd to the Park Avenue Armory for a night that balanced connoisseurship and discovery with high-spirited revelry.

Now in its 72nd edition, The Winter Show remains New York’s longest-running arts, antiques, and design fair; routinely hosting over 70 international dealers to showcase thousands of vetted and covetable historic items spanning the last 5,000 years. “Some dealers have been with us for 60 years, and others are enjoying their first year here,” The Winter Show’s executive director Helen Allen Smith told Vogue. “It’s absolutely thrilling.”

This year’s Opening Night event paid tribute to Caroline Kennedy, a longstanding supporter of The Winter Show who used to frequent Opening Night with her mother, Jacqueline Kennedy Onassis— underscoring the multigenerational legacy that has long been woven into the fabric of the fair.

Guests, including Michael Bloomberg, Reed and Delphine Krakoff, Tonne Goodman, Peter Marino and Cynthia Rowley, and exhibitors sipped Manhattans, espresso martinis, and neat pours while browsing this year’s impressive catalogue, with items ranging from an original Winnie the Pooh manuscript to an 11 carat Tiffany ring dating back to the 1920s. Passed hors d oeuvres like bao buns with garlic sauce, scoops of Black River Caviar, duck-topped sweet potato latkes, and pigs in a blanket kept guests satiated as conversation flowed between exhibitor booths.

At its core, the evening remained grounded in philanthropy. Proceeds from The Winter Show support East Side House Settlement, a Bronx-based nonprofit advancing educational and career opportunities for more than 14,000 residents across the Bronx and Northern Manhattan each year. Under the leadership of executive director Daniel Diaz, the organization has expanded its annual funding from $3 million to $30 million; a testament to how heritage events can evolve into powerful engines for contemporary impact.

The Winter Show is open now at the Park Avenue Armory, 643 Park Avenue, through February 1, 2026.