1. Shop and eat outside at Hester Street FairThis pretty, tree-lined Lower East Side market packs in shoppers every weekend with a killer combination of stylish vintage wares—retro jewelry, antique decor and old-fashioned hats—and one of the best collections of food vendors in Manhattan. Delicious new stalls include Williamsburg darling Pies 'n' Thighs, artisanal ice cream parlor Ample Hills Creamery and boozy cupcakery Prohibition Bakery. Look out for surprising booths, like Compass Yoga who will assess your posture and align in you a suitable pose for $1 on opening day. Hester St at Essex St (hesterstreetfair.com). Sat 10am--6pm. Opens Apr 28.
2. Drink on rooftopsTake advantage of New York's enviable views by getting buzzed at a rooftop bar. Among Manhattan's wealth of hotel toppers, we recommend Upstairs on the 31st floor of the Kimberly. The urbane setting, with ivy-covered walls and nary a cabana in sight, is best experienced at night, when the canopy of lightbulbs strung above the terrace sets off the sight of the Chrysler Building. For more great vistas, check out our guide to rooftop bars in New York. 145 E 50th St between Lexington and Third Aves ( 212-888-1220 , upstairsnyc.com). Mon--Wed 5pm--1am; Thu, Fri 5pm--2am; Sat 11:30am--3:30pm, 6pm--2am; Sun 11:30am--11pm.
3. Celebrate Top Gun Day with a game of volleyballOn May 13 (topgunday.com), grab your wingman, don your aviators, oil up your chest and head to the sand court in Central Park (East of Sheep Meadow, enter at Central Park West and 66th St; 212-310-6600 , centralparknyc.org; daily 6am--1am; free). There's also an asphalt court, but you'll need to bring your own net, and we advise against the slow-mo dive; both courts are first-come, first-served, so arrive early. Remember to rock your best high five, low five. For more places to spike, try these NYC volleyball courts.
4. Be a kid againIt's been five years since Pillow Fight NYC went global, and we still haven't grown up. The seventh annual International Pillow Fight Day is the cornerstone of the Urban Playground Movement, not to mention the one time a year when it's okay to beat a stranger over the head. Last year's event drew 5,000 cushion-wielding New Yorkers to Union Square in a friendly free-for-all. Since it's happening the day before Easter, this year is the Bunny Edition. Wear your floppy ears and your PJs, and let off some steam slumber-party-style. But please, no feathers—they're a nightmare to clean up. Location TBA, R.S.V.P. at newmindspace.com. Apr 7 at 3pm; free.
5. See the work of a shape-shifting artistBy now, Cindy Sherman has become part of a coterie of artists whose works are instantly recognizable by nearly everyone. Starting in the mid-1970s, she hit upon a formula in which the simple child's game of dressing up became a way of interrogating everything from feminism to Hollywood and aging. The results have been some of the most important and influential works of art created in the past 40 years. Sherman is currently the subject of a retrospective at the Museum of Modern Art (11 W 53rd St between Fifth and Sixth Aves; 212-708-9400 , moma.org; $25, seniors $18, students $14, children under 16 free; through June 11). On view are such iconic series as Sherman's "Untitled Film Stills," as well as her self-portraits as subjects from Old Master paintings. The director-photographer-model also offers a new set of works at Metro Pictures (519 W 24th St between Tenth and Eleventh Aves; 212-206-7100 , metropicturesgallery.com; Tue--Sat 10am--6pm; free; Apr 26--June 9), in which she dons garments from the Chanel archive against landscape backdrops.
6. Partake in a spring tradition during HanamiSpring may officially start on March 20, but for us, it doesn't truly feel like the season begins until Hanami—the ancient Japanese tradition of cherry-blossom viewing—at the Brooklyn Botanic Garden. During April, more than 220 trees will flower in varying shades of pink and white. The highest concentration can be found along the Cherry Walk and Esplanade, near the Eastern Parkway entrance of the conservatory; you can also follow the state of the blooms by checking the garden's Cherry Watch map (bbg.org/discover/cherries). The season culminates with the Sakura Matsuri Festival, which celebrates traditional culture from Japan with food, dance performances and a cosplay fashion show. 900 Washington Ave between President and Carroll Sts, Prospect Heights, Brooklyn ( 718-623-7200 , bbg.org). Tue--Fri 8am--6pm; Sat, Sun 10am--6pm. $10, seniors and students $5, children under 12 free. Hanami: Apr 1--29. Sakura Matsuri: Apr 28, 29 10am--6pm
7. Discover a hot spot in Downtown BrooklynDekalb Market made a welcome addition to the outdoor-shopping scene in July 2011, but operator Urban Space is not resting on its laurels. It bursts back on the scene in early April, welcoming old faces and new vendors like Etsy seller Hot Trash Vintage and Park Slope fro-yo fave Culture: An American Yogurt Company to its brightly painted, repurposed shipping containers. But the bigger draw will be the program of events, such as live music on the last Friday of every month, a Down and Derby roller-skating party on the third Friday of every month (beginning May 18) and a lobster boil by the Red Hook Lobster Pound (May 5). If that's not enough, there are also plans afoot for Sunday-afternoon dance parties and bike-in movies. The clincher: The market has secured a license to open up a permanent beer (and wine) garden in early May with picnic tables for 150 people. 138 Willoughby St at Flatbush Ave, Downtown Brooklyn ( 212-529-9262 , dekalbmarket.com). Daily 8am--10pm. Opening early April; check the website or follow @DekalbMarket for updates.
8. Welcome an art-world staple to NYCThe newest addition to New York's slate of art fairs, Frieze New York, is a behemoth: The original Frieze (spun off from the London art magazine of the same name) is one of the biggest events on the art-world calendar, and this edition, which will feature works by 1,000 artists, is sure to add to its prestige. The activities include artist commissions and panel discussions, and will take place under a temporary structure overlooking the East River designed by New York architects SO--IL. Randalls Island Park (friezenewyork.com). May 4--7. Fri--Sat noon--7pm, Sun--Mon noon--6pm. $40; with catalog $70; students, seniors, members of groups of ten or more (after 1pm) $25; children under 16 free. Tickets include bus and ferry service.
9. Party on Saint Paddy'sThe arrival of spring heralds a new season of parades in New York City. For starters, this year marks the 251st year since Gotham's first Saint Patrick's Day Parade (nycstpatricksparade.org; Mar 17 11am--5pm; free). Starting at 44th Street, this celebration of the city's rich Irish heritage marches up Fifth Avenue past Saint Patrick's Cathedral and the Irish American Historical Society, finishing at 79th Street. Later, join burlesque impresario Doc Wasabassco for Saint Patrick's Day for Sinners (The Bell House, 149 7th St between Second and Third Aves, Gowanus, Brooklyn; 718-643-6510 , thebellhouseny.com; Mar 17 8--11pm; $10, redheads free), for a redheaded revue with music, magic and his finest ecdysiasts.
10. Continue your Gaelic merrymakingThe Irish have one day, but the Scots take 12 to celebrate their heritage during Tartan Week with talks, tastings and ceilidhs (a traditional folk-dance party, like line-dancing but with more spinning). The festivities culminate in the National Tartan Day Parade (Apr 14 at 2pm; free), when bagpipers, drummers, the kilted and sundry members of the Scottish-American community promenade on Sixth Avenue. For another opportunity to see kilts flapping in the breeze, enter or watch the Scotland Run 10K in Central Park (Apr 27 at 8am; $23--$40; nyrr.org; free to watch). We're most excited by the week's opening night, the fashion show From Scotland with Love (Apr 26 at 7:30pm; $225, under 30 $99; fromscotlandwithlove.net), where the chances of seeing what's under a celebrity's kilt are fantastically high. Last year cast members from the Broadway show That Championship Season, including Kiefer Sutherland, mooned the audience from the catwalk. Locations, times and prices vary; visit tartanweek.com for more information. Apr 2--24.
