1. TD Five Boro Bike Tour

May 7

Wide-open city streets with no cars? It must be a pipe dream, right? Wrong. On May 7, the TD Five Boro Bike Tour will deliver just that. Riders will have full access to 40 miles of open roads and traffic-free bridges as they bike throughout the five boroughs. Not just a fun activity, the bike tour is primarily a fundraising event and one of the world's largest charitable bike rides. Funds go toward bike education and safety programs, and the event also partners with dozens of nonprofits to raise money for causes that range from cancer research to social services organizations. Cheer riders on, and check out this map to see where they’ll be passing through.

3. Young Picassso in Paris

Beginning May 12

In conjunction with celebrations across the globe that commemorate the 50th anniversary of Picasso’s death, the Guggenheim exhibition Young Picasso in Paris explores the artist’s introduction to the city that would become his permanent home. Beginning with an early representation of the famous dance hall from 1900, Le Moulin de la Galette, the exhibition continues to trace the development of the Spaniard’s artistic voice. Across paintings and works on paper, the exhibition takes visitors through a pivotal year of Picasso’s life and showcases the early experimentation that would come to define his oeuvre.

6. Barry Manilow at Radio City Music Hall

Starts May 31

Grammy, Tony, and Emmy-winning pop artist Barry Manilow returns to his native New York to take the Radio City stage for a limited five-night engagement, marking his 35-39th lifetime performances at the venue. One of the most successful adult contemporary singers of all time, Manilow has sold over 85 million albums, headlined thousands of concerts, and boasts 28 platinum records. Tickets for all five shows are on sale here. Plus, Radio City is right at Rockefeller Center, so enjoy the show, then come have a bite to eat and get a view of the skyline from Top of the Rock.