top of page
  • Kelli

RomCom Walking Tour (on the Upper West Side in NYC)

My last three apartments have all been on the Upper West Side, a large, yet quiet and family-oriented neighborhood West of Central Park, above 59th Street and below 110th (or 96th if you want to get really technical) on the island of Manhattan in New York City. Not only has it been a fantastic area to live in, but I also find it to be incredibly scenic - sandwiched between parks and boasting some of the most gorgeous architecture in the entire city. With waterfront sunset views along the Hudson, dreamy walks in the rain through Central Park, quaint coffee shops, and cozy, dimly-lit bars and restaurants lining every avenue, it's no wonder this area is featured in so many of our favorite Romantic Comedies!

If the weather is particularly exquisite and you find yourself with a couple hours of free time on the Upper West Side, take my ultimate, Self-Guided RomCom Walking Tour and marvel at some of the spots from your favorite moments in cinema. The route begins at Columbus Circle, takes you up through and along Central park up to 96th street, sends you over to Riverside park, and then brings you all the way down through the neighborhood, ending at Lincoln Center. In total, it's just about 4 miles (roughly 8,000 steps)!


#1: Columbus Circle (Enchanted)

Time Warner Center 10 Columbus Circle

Our journey begins in the Southwest corner of Central Park in Columbus Circle, a spot featured a couple times in the film Enchanted. Roger (Patrick Dempsey) works in the Time Warner Center, and Prince Edward (James Marsden) perches here a couple times on his quest for his queen! "The Circle" was designed as part of Frederick Law Olmsted's 1857 vision for Central Park, clearing of the land began in 1868, and the circle was completed and statue of Christopher Columbus was placed in the center in 1892, thus renaming it Columbus Circle. The Time Warner Center, which has been renamed the Deutsche Bank Center began construction in 2000 after a 15 year delay, and was officially completed in 2003. The building consists of two 750-foot towers bridged by a multi-floor mall. The two buildings house offices, residential condominiums, the Mandarin Oriental New York hotel, Jazz at Lincoln Center, and a Whole Foods!

Photos from: On the Set of New York

#2: sheep's meadow (13 going on 30)

Southwestern Central Park, between 66th/69th Streets

Sheep's Meadow is a 15-acre meadow in the Southern part of Central Park. Known to be one of the only flat areas of the park (that is, without trees), it's the perfect spot for picnics and suntanning. In 13 Going on 30, Jenna (Jennifer Garner) has Matt (Mark Ruffalo) meet her here (technically right outside the fenced grassy area) so she can let him know that Poise magazine has decided to hire him for their new redesign launch - a decision that leads to the two spending bundles of time together. This is also one of my personal favorite outfits of Jenna's. Sheep's Meadow gets its name from the flock of Southdown and Dorset sheep that were actually housed on the meadow from 1864 to 1934 where they trimmed the grass and fertilized the lawn. In 1934 they were transferred to Prospect Park in Brooklyn. The sheepfold where they were kept was later converted into Tavern on the Green, a beautiful and popular restaurant nested just inside Central Park.

Photos from On the Set of New York.

#3: the loeb boathouse (27 dresses)

Central Park, Just East of the Lake (even with about 74th Street)

From Sheep's Meadow, walk North for about 15 minutes, past the Bethesda Fountain, until you reach The Loeb Boathouse. This venue is a fantastic place to stop for brunch or lunch, and features stunning views of row-boaters on the neighboring Lake. Aside from being a gorgeous restaurant, it's also an iconic New York City wedding venue. In 27 Dresses, this scene takes place when Jane (Katherine Heigl) agrees to meet with George (Edward Burns) to do a food-tasting at the venue on behalf of her sister, Tess (Malin Åkerman). Kevin "Malcom" Doyle (James Marsden) comes and crashes their flirtatious (albeit completely innocent) rendezvous, and realizes that Jane has feelings for George. It's no wonder that the bratty Tess has visions of having her big day at the boathouse - and for an all-in average base price of $45k, so can you!

Photos from: On the Set of New York

#4: ladies pavilion (the last 5 years)

West 77th Street & West Drive

If you head back West towards the street, you'll encounter Ladies Pavilion just before exiting the park. Tucked away amidst gorgeous greenery with a view of the water and surrounding trees and buildings on the horizon, this gazebo was designed in 1871 by architect Jacob Wrey Mould to be a shelter for carriage riders. Throughout history, the structure went through a bit of TLC, first being moved for its original location closer to 59th street to where it stands today, and in 1973 when it was rebuilt and restored thanks to the group Friends of Central Park. In The Last 5 Years, this is the midway point of the movie, where Jamie (Jeremy Jordan) proposes to Cathy (Anna Kendrick) They also get married here, though we only know that because of the wedding photos in their apartment. This spot is one of those dreamy pockets of Central Park where, for a moment, you don't feel like you're in the city at all.

Photos from: Just Jared.

#5: Museum of natural History (The devil wears prada)

200 Central Park West (between 77th and 81st Streets)

The American Museum of Natural History is one of the most popular museums in all of New York City! Positioned about halfway up the Westside of the park, this icon of the Upper West Side was founded in 1869 and has been featured in TONS of movies (Night at the Museum, Malcom X, Manhattan, and On the Town just to name a few). For the purposes of our tour however, we're going to be looking at it through the lens of The Devil Wears Prada. After Miranda Priestly's first assistant Emily (Emily Blunt) falls ill, Miranda (Meryl Streep) recruits Andrea (Anne Hathaway) to join them for a charity benefit at (you guessed it) the Museum of Natural History. It's here that Andrea first begins to out-perform Emily, but you know what they say about flirting with the Devil... PS - The Museum is also a popular wedding venue here in the city as well, and is ranked #5 on Racked New York's most expensive NYC wedding venues.

Photos from: The Devil Wears Prada

#6: 51 west 95th street (home alone 2: lost in new york)

95th Between Columbus and Central Park West

From the museum, we're going to climb up roughly 15 blocks North to 51 West 95th Street: the heavily-under-construction townhouse belonging to Kevin McAllister's aunt and uncle in the Christmas classic Home Alone 2: Lost in New York. Okay, technically this building is not featured in the actual movie at ALL (that one was actually on the Universal Studios backlot in LA), but if it were locationally accurate, it would be here. Also, if you're in the mood for a quick detour, check out Jillian Mapes's hilariously frustrated, deep-dive article on the chaotic and infuriating geographical inconsistencies in Home Alone 2. I promise you won't be disappointed.

Photos from The Flavorwire and Google Maps.

#7:The plant shed (when harry met sally)

209 West 96th Street

We continue heading West as we make our way to 96th street between Amsterdam and Broadway to The Plant Shed. Featured in When Harry Met Sally during the scene when the couple struggles to carry home a Christmas tree on the snow-covered streets (that's what they get for waiting so long into winter tbh). The Plant Shed still stands today, and has been a family business for more than sixty years, spanning three generations. The movie makes 96th street appear rather quiet, but as you'll see, it's an incredibly busy area, with four lanes of traffic, the express subway station, the cross-town bus, and loads of pedestrians!

Photos from: Sceen-It

#8: 91st street garden (you've got mail)

Riverside Park between 90th & 91 Streets

You've Got Mail is said to be Nora Ephron's love letter to the Upper West Side, and as a result, almost the entire movie is filmed in and around the neighborhood. Of all the spots however, the 91st Street Garden is certainly the most beautiful, and probably the most iconic in terms of the plot. "I wanted it to be you. I wanted it to be you so badly." Cue the sobbing... The 91st Street Garden is run by The Garden People, a group of volunteers founded in 1977 under the West 97-98 Streets Block Association. The original garden was in a vacant lot at Broadway and 96th Street, but when developers seized the land in 1981, they got permission from the NYC Parks Department to start a new garden in this location. Since 1984, the Garden People, Inc. have been tending and maintaining this area. The organization does accept volunteers of all gardening backgrounds, though at the time of this article, volunteer onboarding has been suspended due to the COVID-19 pandemic.

Photos from: On the Set of New York

#9: Café lalo (you've got mail)

201 West 83rd Street

We begin our descent down through the neighborhood and continue on our You've Got Mail streak with Café Lalo, featured in one of the most memorable scenes in the movie. When Joe Fox (played by the inimitable Tom Hanks) realizes that his internet companion, "Shop-Girl" is actually his business nemesis Kathleen Kelly (played by the timeless Meg Ryan), he uses his newfound knowledge to bust her chops about getting stood up. Pop into Café Lalo for any of their pastries or desserts and a cappuccino before finishing out the rest of the tour!

Photos from: Scene-It

#10: the ansonia (Uptown Girls)

2109 Broadway (between 73rd and 74th Streets)

This architectural beauty sits on Broadway between 73rd and 74th streets, and is Molly Gunn's lavish apartment in Uptown Girls (well, ya know...before she goes broke and gets evicted). This building was erected between 1899 and 1904, and was originally constructed as a lavish hotel. In 1992 however, it was converted to a condominium, and as of today, if you have a cool $3.6 mil, you too could live the life of lavish luxury in one of its 425 units.

Photos from: On the Set of New York and Corcoran.

#11: Café luxembourg (when harry met sally)

200 W. 70th Street

When Harry Met Sally is also too iconic to not hit twice, and the scene that takes place at Café Luxembourg is one of my favs. With our two main characters, Harry (Billy Crystal) and Sally (Meg Ryan), set each other up with two of their friends, Marie (Carrie Fisher) and Jess (Bruno Kirby). Spoiler alert: The evening goes a different direction than the two originally anticipate, and their dates end up falling for each other (and even get married later in the movie)! The restaurant was quite trendy when the film was released in 1989 - Marie even says "Restaurants are to people in the 80s what theaters were to people in the 60s. I read it in a magazine." Café Lux opened in 1983 and draws crowds for its accessible New-American fare and art deco-influenced dining room. Today it is still an Upper West Side fav.

Photos from: A Dash of Cinema

#12: westside restaurant (little manhattan)

2020 Broadway & 69th St.

Westside Restaurant is your basic Upper West Side diner, and also the setting for the final scene of the film Little Manhattan, an earnest, pseudo-coming-of-age story that emphasizes the importance of intentional communication and how your first love, no matter how young you may be when you find them, will always be irreplaceable. When Gabe narrates "...I'm never gonna get another first love. That one's always gonna be her," You can BET I become UNDONE!!

Photos from: On the Set of New York

#13: Lincoln Center (Sweet Home Alabama)

Columbus Ave between 62nd & 65th

We conclude our tour of the Upper West Side at one of the most iconic venues in all of New York City: Lincoln Center. This is the spot in Sweet Home Alabama when Melanie (Reese Witherspoon) is outed as an engaged woman by her future mother-in-law (Candice Bergen) and immediately mobbed by the paparazzi. Other iconic movies that have filmed at Lincoln Center are: Black Swan, Center Stage, Ghostbusters, and The Producers. For curious minds, Lincoln Center does allow private events, but weddings are not super common here. Though if you were perusing venues, might I suggest the Stanley H. Kaplan Penthouse.

Photos from: On the Set of New York.


I hope you enjoyed this self-guided walking tour through the Upper West Side!!! Romantic comedies are my absolute favorite, and every time I see a scene filmed in my neighborhood I always fangirl. Make sure you tag me on Instagram if you end up embarking on this 4 mile adventure, and comment below if there are any of your favorite iconic RomCom scenes that I missed!!

Until next time!



Recent Posts

See All
bottom of page