101 things to do in the winter in New York City 2011

Mark your calendar for classic holiday events, warming treats, cultural highlights and more!

  • Photograph: Paul Wagtouicz

    Yo La Tengo

  • Photograph: Jason Rodgers

    New York Rangers

  • Philip Glass

  • Photograph: Andrew Fladeboe

    Trump Wollman Rink

  • Photograph: Lizz Kuehl

    Have a seasonal cocktail

  • Photograph: Courtesy the Museum of the City of New York

    "The Greatest Grid" at the Museum of the City of New York

  • Photograph: Courtesy of Merge Records

    Jeff Mangum live

  • Photograph: Eric Harvey Brown

    Bowie Ball

  • Photograph: Courtesy of Radio City Music Hall

    Art deco apartment inside Radio City Music Hall

  • Photograph: Courtesy Big Onion Walking Tours

    Big Onion Walking Tour

Photograph: Paul Wagtouicz

Yo La Tengo

21. Celebrate Hanukkah with eight nights of Yo La Tengo
In what's become an annual tradition, the Hoboken indie-rock trio takes to its neighborhood venue for eight nights, coinciding with the Festival of Lights. Seeing the venerable group play through its extensive back catalog (as well as the occasional cover) is reason enough to attend. But you'll also see a bevy of awesome surprise guests: Last year's visitors included M. Ward, Bonnie "Prince" Billy, the National and comics Marc Maron and Jim Gaffigan. If you missed getting tickets, don't fret—reasonably priced stubs should appear on Craigslist near the date of the show. Maxwell's, 1039 Washington St at 11th St, Hoboken, NJ (201-653-1703, maxwellsnj.com). Dec 20--27 8:30pm; sold out.

22. Cheer on the Rangers at a renovated arena
To keep its reputation as one of the world's greatest arenas, Madison Square Garden is undergoing a massive overhaul over three consecutive summers. Phase one, which revamped the lower bowl, has already ushered in several new food options, courtesy of celebrity chefs like Jean-Georges Vongerichten, who created an Asian-influenced Simply Chicken stand, and Andrew Carmellini of the Dutch, who developed the Sausage Boss counter. (Phases two and three, which will address the arena's upper levels, will happen over the next year.) See the work in progress at a New York Rangers game. Madison Square Garden, 4 Pennsylvania Plaza (Seventh Ave) between 31st and 33rd Sts (212-465-6741, thegarden.com). Schedule varies; visit website for details. $39--$1,200; through Apr 7.

23. A modern master gets a birthday blowout
Philip Glass's 75th birthday provides the impetus for the Park Avenue Armory's second Tune-In festival. Over four days, the composer, his influences, collaborators and disciples will stage performances in the imposing Wade Thompson Drill Hall. Glass himself will perform with Patti Smith, and producer Hal Willner will collaborate with artist Ralph Steadman and guitarist Bill Frisell to augment a reading of Allen Ginsberg's influential poem Kaddish. 643 Park Ave between 66th and 67th Sts (212-933-5812, armoryonpark.org). Times vary; $15--$50. Feb 23--26.

24. Take a twirl on an ice-skating rink
'Tis the season to strap on a pair of skates and do your best Johnny Weir impersonation. Fantastic views can be found at the Trump Wollman Rink (Central Park, enter at W 59th St and Sixth Ave; 212-439-6900, wollmanskatingrink.com; Mon, Tue 10am--2:30pm; Wed, Thu 10am--10pm; Fri, Sat 10am--11pm; Sun 10am--9pm; $16--$16.75, seniors $4.75--$8.25, children 11 and under $5.75--$6; skate rental $6.75), although there won't be room for speed skating or fancy tricks. For a little more breathing room, head to Citi Pond at Bryant Park (Sixth Ave between 40th and 42nd Sts; 212-661-6640, citipondatbryantpark.com; Mon--Thu, Sun 8am--10pm; Fri, Sat 8am--midnight; free; skate rental $14). The massive rink is open late; we suggest going during off-hours if you want to practice your triple lutzes in relative peace. Check out our guide to the city's rinks for more skating spots.

25. Sip a seasonal cocktail
The flavors found in holiday feasts inform some of our favorite seasonal drinks. The A La Mode ($11) at Dutch Kills (27-24 Jackson Ave at Dutch Kills St, Long Island City, Queens; 718-383-2724), for example, mixes hot cider with Elijah Craig bourbon and vanilla-scented Spanish liqueur Licor 43; the drink is topped off with whipped cream from a local dairy and a pinch of freshly grated nutmeg. Or try the Port of Call ($12) at Clover Club (210 Smith St between Baltic and Butler Sts, Cobble Hill, Brooklyn; 718-855-7939), which combines fresh cranberry preserves, house-made cinnamon-bark syrup, Gordon's Gin and Bitter Truth Jerry Thomas Own Decanter Bitters.

26. Find out how order came to New York City's streets
Thanks to the numbered grid that defines the layout of Manhattan's avenues and streets, it's nearly impossible to get lost in the borough (assuming you're not trying to navigate the labyrinth that is the West Village). Learn about the Commissioner's Plan of 1811, which established the pattern, in "The Greatest Grid: The Master Plan of Manhattan, 1811--2011," a new exhibit opening at the Museum of the City of New York. Rare artifacts and documents—including a hand-drawn map of the Commissioner's Plan—illustrate how the grid came to be. 1220 Fifth Ave between 103rd and 104th Sts (212-534-1672, mcny.org). Daily 10am--6pm; suggested admission $10, seniors and students $6, children under 12 and members free. Dec 6--Apr 15.

27. Catch Jeff Mangum at BAM
After releasing two fantastic records with his band Neutral Milk Hotel in the late '90s, On Avery Island and In the Aeroplane Over the Sea, songwriter Jeff Mangum slipped into obscurity. Now, well over a decade later, the frontman has resurfaced curating this year's All Tomorrow's Parties festival, making an appearance at Occupy Wall Street and playing a handful of solo shows. If either of those aforementioned records means anything to you (and even if they don't), don't miss this three-night run in Brooklyn from the reclusive artist. BAM Howard Gilman Opera House, 30 Lafayette Ave between Ashland Pl and St. Felix St, Fort Greene, Brooklyn (718-636-4100, bam.org). Jan 19--21 8pm. $35.

28. Dress up like Aladdin Sane for Bowieball 2011
Smear yourself with glitter and don a bright red mullet at this annual extravaganza devoted to glam-rock god David Bowie. The show features performances by Amber Martin and Bridget Everett, Michael Cavadias, Lady Rizo and LeRoi the Girl Boy, who will pay tribute to Bowie with music, burlesque and dance. DJ Jake B will spin his custom Bowie mash-ups, and after getting a gratis hair-and-makeup makeover, enter the costume contest to win gift certificates and other prizes. Le Poisson Rouge, 158 Bleecker St at Thompson St (212-505-3478, lepoissonrouge.com). Dec 17 11pm--4am; $20, advance $15, after 12:30am $25.

29. Reclaim the city's tourist-filled venues
Instead of griping about how much you hate dealing with the crowds during the holidays, embrace that little part of you that loves quintessential New York City venues—don't pretend like it doesn't exist—and revisit some of the city's iconic spots. Plus, you can impress your friends with little-known facts about each place; for example, were you aware that you can visit a plush, Art Deco apartment within Radio City Music Hall (1260 Sixth Ave at 50th St; 212-247-4777, radiocity.com)? Or that a secret track exists in Grand Central Terminal (44th St between Vanderbilt and Lexington Aves; 212-340-2583, grandcentralterminal.com)? We bet these touristy spots don't seem so boring now. For more hidden details of iconic city venues, check out our recent feature devoted to the secrets of classic New York.

30. Bundle up and learn about the NYC's history
Big Onion Walking Tours launched two new excursions in October. "Satan's Seat: New York During Prohibition" (meet at the northeast corner of Bowery and E Houston St) was created as a companion to Ken Burns's recent PBS documentary, Prohibition, and focuses on the history and culture of the city during the Roaring '20s. Across the river, the Historic Brooklyn Heights tour (meet on the stairs at Brooklyn Borough Hall facing Cadman Plaza) takes trekkers through the Kings County neighborhood, while offering tidbits on its famous residents and landmarks, such as the Plymouth Church of the Pilgrims, which may have been used as a stop on the Underground Railroad. Times vary; for more information, visit bigonion.com. $15--$18.