•Shakespeare in the Park (June through September) always puts on a reliably entertaining – and sometimes star-studded (Meryl Streep, Kevin Kline) – outdoor show, though the first-come first-served tickets (two per person) can be brutally hard to come by (free).
• Bring a blanket to the Bryant Park Film Festival on a Monday between June and August to catch classic movies under the stars (free).
• Enjoy a class of wine while listening to your favorite operas during the Metropolitan Opera in the Parks in June (free).
• If you're hip to jazz, the JVC Jazz Festival presents nearly 200 concerts in June with such stars as Eartha Kitt and Branson Marsalis.
• Finally, Summer Restaurant Week offers prix-fixe discounts to entice you away from all the outdoor fun.
July This month is all about music, movies…and Macy's.
• If you're not lucky enough to be invited to a rooftop party, you'll have to grab a seat early in the day for a good view of Macy's 4th of July Fireworks.
• New York Philharmonic in the Parks sets up their instruments at a different green space throughout the tri-state area every evening for a week (free).
• If classical's not your scene, head to Coney Island for the indie Siren Music Festival (free) or catch local bands and DJs at the Sunday Pool Parties at McCarren Pool in Williamsburg, Brooklyn (free).
• In a city where few people have cars, an alternative to the drive-in movie is a "sit-in" – RiverFlicks shows movies at Hudson Piers (one pier geared toward kids and one to adults), while the Brooklyn Bridge Park Summer Film Series screens classic films under the shadow of the famous bridge during July and August (free).
AugustThe time when everyone who actually lives in NYC seems to have split for the beach.
• If you're one of the few stuck in town, the sticky, sultry weather makes it more appealing to try some indoor events, like the New York International Fringe Festival, 10 days of more than 200 performances at small theaters around the city. (Though beware: Not all are air-conditioned.)
• Evening weather is a little more pleasant – the perfect time to catch a dance or world music performance at Lincoln Center Out of Doors (free).
September The locals return from their beach houses and the city's cultural institutions welcome them with open arms.
• Broadway shows go into previews, the Metropolitan Opera begins its fall season and New York Fashion Week shows off next spring's hottest clothes.
• For affordable arts fare, the Fall for Dance Festival at New York City Center features a varied roster of well-known dance companies as Bill T. Jones/Arnie Zane, Paul Taylor, Martha Graham and NYC Ballet mixed in with more obscure performers. Tickets for all performances are a mere $10.
• The New York Film Festival at Lincoln Center opens with film premieres and chats with directors like Wes Anderson and Sidney Lumet.
• The Feast of San Gennaro is either heaven-sent or straight from hell, depending upon your point of view. For 10 days, thousands of people descend upon Little Italy to gorge themselves on zeppolis and fried Oreos while playing carnival games and ogling the last-days-of-summer outfits worn by the boisterous crowd (free, though you won't get away without spending something).
October The city celebrates creativity in many guises this month.
• The CMJ Music Marathon and Film Festival brings together hundreds of bands for five days at venues all over the city.