Every city has its favorite season. Think of a convertible cruising along Sunset Boulevard on a summer evening in Los Angeles; the powdery slopes and cozy lodges just west of Denver in the winter; the early spring blossoms of Atlanta’s gardens. But autumn in New York may trump them all. Sandwiched between heavy-lidded summer and white-knuckled winter, autumn in New York can be an unpredictable middle child. Late warm fronts from the Gulf of Mexico can prolong the fine weather, inspiring long foliage walks. Just as easily, the frigid northern wind may awaken early, sweeping into the city and giving New Yorkers an excuse to seek refuge in a well-worn bar. Either way, it’s the finest time of the year to visit the Big Apple. As Billie Holiday, Frank Sinatra and Ella Fitzgerald have sung, “It’s autumn in New York, it’s good to live it again.”
Fifth Avenue Shopping Tour
NEW YORK MAY SEEM strange to some visitors: the tiny apartments with bathtubs in the kitchen, the seeming suspension of all traffic laws within city limits. But shopping is an international language. Whether you’re a first-time visitor or a lifetime Gothamite, when the air cools and thoughts turn to holiday gift giving, there’s no better thoroughfare in the world than Fifth Avenue to pick up something for everyone on your list.
Beginning at 59th Street and Fifth Avenue (the southeast corner of Central Park), head south along New York’s historic boulevard of the rich and powerful, stopping first at legendary department store Bergdorf Goodman (www..bergdorfgoodman.com), your one-stop spot for high-end fashion like Chanel, Armani and Yves Saint Laurent.
Right next door is the greatest toy store in the world, FAO Schwarz (www.fao.com), which underwent an impressive renovation in 2004—but don’t worry, the famous “walk-on” piano from Big is still there. Just across the intersection, at the 57th Street corner, lies Tiffany & Co. (www.tiffany.com), the upscale jeweler that made Audrey Hepburn swoon in Breakfast at Tiffany’s—and will likely cause the same reaction from anyone lucky enough to get a trademark “Tiffany blue” box for Christmas.
Seasonal Kitchens
NO DISRESPECT TO STEAKHOUSES—Peter Luger Steakhouse (www..peterluger.com; 718-387-7400) is legendary—but for every new restaurateur resurrecting the same-old inch-thick strip and creamed spinach combo, there’s an innovative chef experimenting with a locally grown, seasonally inspired menu. And the bright squashes, sweet potatoes and pears that represent autumn’s bounty are finding their way into the city’s seasonal kitchens.
In the 19th century, Five Points was the name of a tenement-encrusted slum in lower Manhattan. Now the tenements are condos, and Five Points (www.fivepointsrestaurant.com; 212-253-5700) is the name of an unpretentious restaurant with a nightly changing menu. The food reflects the current produce at the green market, and you can generally count on savory fall standards like butternut squash cappellacci or a house-cured, double-cut pork chop with roasted applesauce.
Applewood (www.applewoodny.com; 718-768-2044), in Brooklyn, also embraces locally grown, seasonally inspired fare. It hosts Meet-the-Farmer dinners, where foodies can relax in the fireplace-warmed dining room with an autumn-inspired cocktail, enjoy a four-course tasting menu and learn more about where their meals came from. These events are popular and private, so call ahead for reservations.
Culture Breaks
AT THIS POINT, THE SHOPPING spree has taken you down about three blocks, so you’re more than likely weighed down with a few purchases. Take a moment to think of your credit card bill; it might be time for a brief architectural/cultural break. Even though there are plenty of high-end boutiques between 57th and 50th streets (Cartier, Harry Winston, Gucci, to name a few), put up the blinders until you get to 50th Street, where you’ll find the understated elegance of America’s first Catholic cathedral, St. Patrick’s Cathedral (www.saintpatrickscathedral.org). Dedicated in 1879, this gem of Gothic architecture has been scene to the funerals of such luminaries as Babe Ruth and Robert F. Kennedy.
Directly across from St. Patrick’s is the one-of-a-kind Rockefeller Center (www..rockefellercenter.com), John D. Rockefeller’s gift to the city. Completed in 1935, the centerpiece G.E. Building is the backdrop for the annual Christmas tree lighting—just after Thanksgiving—along with the most iconic ice rink in the world.
Okay, now you can return to shopping, but do it at a cultural wonderland. Head to the Museum of Modern Art Design and Book Store (www.momastore.org) at 53rd Street. From furniture, home accessories, unique objets d’art and jewelry to kids games and books, shopping at the MoMA store affords you the comfort of knowing you’re getting both long-lasting quality and originality in whatever you buy.
Outdoor Activities
GRANTED, SHOPPING IN NEW YORK is a lot like a competitive sport, but while you’re in town you might want to actually get in a little real exercise. For those unafraid of taking a tumble or two, there’s nothing quite like an afternoon of ice skating at Central Park’s Wollman Rink (www..wollmanskatingrink.com). Unlike the rink at Rockefeller Center, which is more about dodging fellow skaters than actually skating, Wollman Rink gives you plenty of room to stretch your legs and offers spectacular views of the park and surrounding skyline. Starting in October, Wollman offers rental skates for five dollars (plus a skating fee), so take advantage of a chance to work up your appetite and earn a post-skate hot toddy.
Though New York is often thought of as a grid of concrete and steel, it is actually a beautiful place, where you can take in the vivid colors of fall foliage. Peak viewing is usually from the end of October through the middle of November. Central Park (www..centralparknyc.org)—with its robust population of maples, oaks and elms (don’t miss the spectacular 110-foot American Elm near 5th Avenue and 97th Street)—defines autumn in New York. As you witness the leaves turning from light golden yellow to deep red, it’s easy to appreciate the rare beauty of the season in the Big Apple.
Tavern Town
AS THE COOLER FALL weather ushers New Yorkers indoors, it becomes apparent that the city has a drinking culture (but not a drinking problem). Sure, you can find the techno beat and pastel drinks of a resort or the cheap pitcher-of-beer obliteration of a university town. But those are fringe elements, tourist traps and doomed chain imports. Despite the endless cycle of new pub openings and last calls every week, there’s a sense of permanence and place in New York’s bar culture.
The roots date back to 1940s Midtown office workers in handcrafted wing tips grabbing Gibsons before hopping on the 5:42 to Westchester. Or before that, the great writer-drinker-poets of the 1920s breaking into ballads in the Village’s bohemian bars. Going back even further, politicians and generals planned campaigns and wars in Downtown’s polished brass pubs over bottles of claret.
A great New York bar is at its best in autumn, when the crisp air makes a tavern’s warm glow especially inviting. In the Upper East Side, you’re never far from an Irish pub or a fancy hotel piano bar. But if you’re looking for a cozy place to escape the chill after a long walk in Central Park, the red velvet drapes and crackling fireplace at The Auction House (212-427-4458) will warm your spirits and thaw your feet. There’s no sign out front, so look out for the red-curtained windows.
There are more classic bars in the Village than in any other Manhattan neighborhood. KGB Bar (www.kgbbar.com; 212-505-3360) and the White Horse Tavern (212-243-9260)—Dylan Thomas’ favorite watering hole—are both pilgrimage sites for literary types. The Spotted Pig (www.thespottedpig. com; 212-620-0393) is relatively new to the West Village’s tavern pantheon, but it’s destined for classic status. The Michelin Star-awarded gastropub features hand-pumped cask conditioned ales.
Union Hall (www.unionhallny. com; 718-638-4400), in Brooklyn’s Park Slope neighborhood, resembles the kind of establishment where the Explorers Club might have met to discuss the feasibility of crossing the Pacific in a balsa wood raft. The leather chairs, floor-to-ceiling bookshelves and huge stone fireplace recreate a classic clubby atmosphere without being kitsch.
Holiday Events
HALLOWEEN
MUST SEE: THE 34TH ANNUAL VILLAGE HALLOWEEN PARADE
On October 31, join tens of thousands of costumed partiers, hundreds of puppets and 53 marching bands as they turn 6th Avenue into a river of revelers. www.halloween-nyc.com
WHERE TO GET YOUR COSTUME: HALLOWEEN ADVENTURE
From horror masks to superhero getups, this East Village costume mega store has all the bases covered. www.halloweenadventure.com
SHOULD SEE: ING NEW YORK CITY MARATHON
Even if you’re not participating in the race on November 4, cheering on the runners as they speed on by can be exhilarating. www.nycmarathon.org
THANKSGIVING
MUST SEE: MACY’S THANKSGIVING DAY PARADE
On November 22, enormous cartoon character balloons float down Broadway. Enough said. www.macysparade.com
WHERE TO CATCH THE PARADE:
Why compete with the crowds that line up in the cold wee hours of the morning? Book a room with parade views at the W New York Times Square (www.starwoodhotels.com) or Doubletree Guest Suites Times Square (www.doubletree.com).
ALSO SEE: VETERANS DAY PARADE
On November 11, salute the nation’s bravest as they march up 5th Avenue from 23rd Street to 59th Street.
CHRISTMAS
MUST SEE: THE ROCKEFELLER CENTER CHRISTMAS TREE
The minimum height requirement for the tree (usually a Norway Spruce) is 65 feet, and it’s decorated with about 35,000 lights. It’s like the Grand Canyon: much bigger in person than it seems on TV. www.rockefellercenter.com
SHOULD SEE: THE ORIGAMI HOLIDAY TREE.
Representing months of paper folding, this tree—at the American Museum of Natural History—is much smaller, but just as impressive, as the one at Rockefeller Center. www.amnh.org
WHERE TO FIND LAST-MINUTE GIFTS: HOLIDAY MARKET AT UNION SQUARE
Dozens of red-and-white-striped tents pop up around the holidays, turning Union Square into a trinket and novelty bazaar. www.unionsquarenyc.org

