The Winter Show
The Winter Show — née Winter Antiques Show — is an annual benefit supporting East Side House Settlement’s community programs. It’s also the standout art, antique, and design fair in a very crowded field. Returning to the Park Avenue Armory for its 65th anniversary, the show boasts 68 top experts in fine and decorative arts from across the globe and a diverse collection of works from antiquity up through the present day. New York design editor Wendy Goodman will be participating, naturally. She is hosting the glamorous Young Collectors Night fête on January 24 alongside Zac Posen. She’ll also host an intimate discussion of her latest book, May I Come In? on the evening of January 25.

Outsider Art Fair
Now in its 27th New York City edition, the Outsider Art Fair, running January 17–20 at the Metropolitan Pavilion, is like the Winter Show’s cooler younger sister. OAF is the only fair dedicated to self-taught artists, art brut, and outsider art. The fair showcases 67 exhibitors from 37 cities in seven different countries, with eight first-time galleries appearing. This year’s curated spaces are “Good Kids: Underground Comics from China,” displaying zines and original drawings by Chinese artists that are too controversial to distribute in mainland China, as well as an homage to the late art dealer Phyllis Kind, who championed outsider artists long before her contemporaries took them seriously.

In Our Time: A Year of Architecture in a Day
During this January 19 symposium, the Met presents an impressive roster of contemporary architects, artists, photographers, writers, and filmmakers, who will share the best spatial projects of the past year. You will hear from architects working in Nigeria, Brazil, Mexico, and China. You’ll learn about an opera performed on New York City’s High Line. You’ll get familiar with the work of the pioneer of New Andean Architecture, who is shedding light on the architecture of the indigenous cultures of Bolivia.