Walking Tour

Re-creating “You’ve Got Mail” on the Upper West Side

Throw on your best cardigan for a leisurely stroll around the neighborhood spots that define the quintessential New York romantic comedy.

Every local—and the WSWD?! staff—has his or her own favorite New York movie. Mine happens to be a cinematic time capsule taking viewers back to a simpler time when chat rooms replaced Tinder swipes and indie bookshops were warring against chain stores. If youve been living under a cobblestone street for the past two decades, Youve Got Mail tells the charming tale of well-read rivals-turned-lovers Joe Fox (Tom Hanks) and Kathleen Kelly (Meg Ryan) as they butt heads while unknowingly falling in love over dial-up.

Instant messaging and big-box bookstores are quickly becoming extinct, but the timelessness of the neighborhood in which Mail is set certainly isnt (and neither is the movies original website). Take a day to re-create some of my favorite scenes around the Upper West Side; dont get too embarrassed if you end up quoting the entire flick, line by line, in the streets.

9:30 a.m.: Breakfast at Barney Greengrass

Start your day off at this storied delicatessen, which has been slicing up smoked fish and babka to the masses since 1908. A hearty breakfast of eggs with a side of pastrami salmon is needed to get through your friend’s sordid tales of lovers lost—perhaps a former Fascist dictator from Spain? 541 Amsterdam Avenue (at West 86th Street)

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Salmon pastrami and eggs with a side of schmear / Photo by Stefano Giovannini

11:15 a.m.: Catch a Matinee at AMC Loews Lincoln Square 13

The beginning of the end of Kathleen’s relationship with her writer boyfriend may have happened at this cushy cineplex, but our love for the reserved seating here and one of the city’s only legit IMAX screens goes on. 1998 Broadway (at West 68th Street)

2 p.m.: Pack Your Picnic at Zabar’s

A neighborhood mainstay since 1934, this mom-and-pop grocery store is the quintessential stop for all your picnicking essentials. Before you head off for a Riverside romp, fill your basket with jams imported from France, wheels of Brie, and lox cured in-house. Just don’t dare attempt to use your credit card on the cash-only line2245 Broadway (at West 80th Street)

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Fresh cheese, please / Photo by Stefano Giovannini

3:45 p.m.: Stroll Through the 91st Street Community Garden

The quaint flower patch tucked inside Riverside Park has been run by green-thumbed volunteers since its inception in 1977. Blossoming perennials of all kinds bloom throughout the seasons, so no two strolls will be alike. Should you find yourself tearing up from the pollen (or from the overwhelming feeling of meeting your online love interest IRL), chances are you’ll run into a few fellow lovebirds to lend you an embroidered hankie. Riverside Park (between West 90th and 91st Streets)

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Meet your beau in the middle of the garden / Photo courtesy of New York City Department of Parks & Recreation

5:15 p.m.: Eat Dessert Before Dinner at Cafe Lalo

It would be impossible to stand up any date once you browse the sprawling dessert display at this Euro-style patisserie. Order a herbaceous tea like Kathleen would, and treat yourself to a lavish strawberry tart while you’re flipping through your worn-out copy of Pride and Prejudice201 West 83rd Street (between Broadway and Amsterdam Avenue)

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Take a bite into this / Photo by Stefano Giovannini

7 p.m.: Grab Cheap Eats at Gray’s Papaya

Hope you’re OK with a standing-only dinner date. Though our economy has stabilized, Gray’s Recession Special remains one of the best deals in town: Two griddled franks topped with tangy sauerkraut and taxi-yellow mustard and a signature fruit juice cost a little more than a Lincoln and fills you up for the rest of the night. 2090 Broadway (at West 72nd Street)

We can re-create a day from any of your favorite NYC-based movies. Just get in touch with an experience adviser for more help. Find more curated Walking Tours in NYC in The Guide.