Over the Victoria Day long weekend, my boyfriend and I are driving down to New York City. We’ve gone every year for the last four, and each time we visit we discover new reasons to love the city. In 2011, for example, we rented road bikes and toured around Manhattan, then crossed over the Brooklyn Bridge, checked out Prospect Park and went down to Coney Island. It took us a whole day and we were exhausted by the time we hit the Atlantic, but it was great. We were both impressed by the miles of dedicated bike lanes that made cycling feel so much safer than in our home town of Toronto.

We might bike around again, but I think this trip is going to be more arts and culture focused. Here’s what we’re thinking of seeing.

Milstein Hall at Cornell University

Milstein Hall by OMA

Milstein Hall by OMA

On our drive down from Toronto we’re planning to stop in Ithaca to see Cornell University, and the the new addition to their architecture school — Milstein Hall. It was designed by one of the world’s most celebrated yet controversial design firms, OMA, and is the first addition to the architecture school in over 100 years. I’ve been to two OMA buildings, one which I loved — the Kunsthal in Rotterdam — and one which I didn’t like — the McCormick Tribune Campus Center in Chicago (the giant portrait of Mies van der Rohe on the entryway just seemed tacky). Based on photos, I’m not sure what I’ll think of Milstein Hall. The giant cantilever looks cool from the outside (top), but the inside looks a little bit Logan’s Run (which is never a good thing).

Cindy Sherman at the MoMA

Cindy Sherman. Untitled #466. 2008. Chromogenic color print, 8′ 1 1/8 x 63 15/16″ (246.7 x 162.4 cm). The Museum of Modern Art, New York. Acquired through the generosity of Robert B. Menschel in honor of Jerry I. Speyer. © 2011 Cindy Sherman

The last time I saw a Cindy Sherman show was 1999 when I was in grade 11. The show was at the Art Gallery of Ontario, and I was probably more excited for the Chinese food I was going to grab for lunch than Sherman’s meticulously composed photography. I’m glad my 15-year-old self won’t be my last impression of this important artist’s work.

Schiaparelli and Prada: Impossible Conversations

Schiaparelli and Prada: Impossible Conversations

I know nothing about Elsa Schiaparelli. I don’t know that much about Miuccia Prada either, other than her geek-chic clothing and ubiquitous black purses. And the idea of an “impossible conversation” — a fictionalized dialogue between two people who’ve never met — seems a little too surreal for me. But I’m willing to see anything that the New Yorker says is cool. Plus, last year’s Costume Institute show — Alexander McQueen: Savage Beauty —was so stunning, I would go if they put on a show about finger puppets and clown makeup.

The Steins Collect at the Metropolitan Museum of Art

Henri Matisse’s Woman With a Hat in the Steins Collection

I’ve been fascinated with Gertrude Stein since long before Kathy Bates brought her to life in Woody Allen’s Midnight in Paris. One of my earliest introductions to her comes from John Glassco’s book, Memoirs of Montparnasse. This is how he captured the writer, art collector and supporter of Picasso and Hemingway:

“Gertrude Stein projected a remarkable power, possibly due to the atmosphere of adulation that surrounded her: a rhomboidal woman dressed in a floor length gown apparently made of burlap, she gave the impression of absolute irrefragability; her ankles, almost concealed by the hieratic folds of her dress, were like the pillars of a temple: it was impossible to conceive of her lying down.”

I’m really looking forward to seeing the pieces she collected with her brothers Leo and Michael. The entire time I’m wondering between the Cezannes and Matisses, I’ll be imagining how it would have felt to see the great, rhoboidal lady in person, and attend one of her artist and writer-filled parties.

April Bloomfield’s The Spotted Pig

I don’t eat red meat but I’ve heard and read so much about April Bloomfield’s chargrilled burger with roquefort cheese (no substitutions or ketchup allowed), I would gladly make an exception. I might even spot Jay-Z.