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I went on the Taylor Swift walking tour of NYC and found my inner Swiftie (sort of)

A self-proclaimed Taylor Swift skeptic embarks on a walking tour of NYC to explore the singer's connection to the city. Here's what happened.

Anna Rahmanan
Written by
Anna Rahmanan
Senior National News Editor
Taylor Swift walking tour of NYC
Photograph: GetYourGuide
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Full disclosure: Taylor Swift actively irritates me. 

Washington Square Park arch
Photograph: Anna Rahmanan

Although I marvel at her success and sometimes find myself listening to some of her songs—"Love Story" and "You Belong With Me," courtesy of my Swiftie daughters—there is something about Swift the celebrity that just rubs me the wrong way. 

According to my unofficial self-therapy sessions, it’s Swift’s apparent constant complaints about her breakups—which, let’s be honest, have fueled her wild success—that paint this unlikable picture of her in my own eyes. After all, we’ve all been there. My heart has been broken by men and friends, without the cushion of millions of fans supporting me throughout it all, and here I am not complaining and not constantly talking about it.

New York, in my head, belongs to the sorts of people that, yes, complain, but are resilient and move on to the next thing in no time, without dwelling on the past too much. Given her deep ties to Kansas City, where her boyfriend Travis Kelce plays professional football, Nashville and Los Angeles, can’t Swift just leave New York alone?

Taylor Swift walking tour of NYC
Photograph: GetYourGuide

Given all that anger, when I got an email from On Location Tours and GetYourGuide about their newly launched NYC guided tour for Swift fans, I just had to go, at least to better direct my annoyances. How dare Swift, a darling of the country music world, lay claim to my city, one that she has written about and owns (beautiful!) real estate in but is only one of my towns that she has homes in?

After a number of weather- and calendar-related reschedules, I met “ultimate Swiftie” Hannah Kulawiak on a freezing December morning inside Housing Works Bookstore in Nolita, which, as fans of the star obviously know and I didn’t, was the site of Swift’s “All Too Well” music video.

The downtown bookstore fully embraces its status as a Swiftie hotspot: there is a sign on the floor that reads “Taylor stood here.”

Washington Square Park
Photograph: Anna Rahmanan

Wondering how I’d recognize Kulawiak, all questions drifted away as soon as I stepped inside. If you had told me my tour guide was Swift herself, I would have believed you.

Boasting the artist’s signature blonde bob and bright red lipstick, I couldn’t tell if Kulawiak purposely dressed the part or if her beautiful blue eyes and white complexion just lent themselves to the task at hand. I actually still don’t know, but I suspect it was a combination of both things. After all, Kulawiak is a devoted fan who went through a rigorous process to land the tour guide job.

She tells me all about the process while we walk to the next step, Washington Square Park.

“My roommate sent me an ad about a contest held to find the ultimate guide so I applied,” says the 24-year-old aspiring actress, who moved to New York from Cleveland, Ohio, a little over a year ago. “They vetted me, asked me about my background and relationship to Swift. I told them how she’s always been a part of my life. I never met her but I wish I did!”

Housing Works Bookstore
Photograph: Anna Rahmanan

Kulawiak has, however, seen Swift live in concert twice—which is saying a lot, considering the hardships involved in snagging tickets to any of her shows. 

It’s worth noting that Kulawiak helped organize the tour, advising on which stops she thought she should be making and landing on a total of 13 that the organizing bodies are cagey about releasing name by name. After all, fans could end up taking the tour, which is not officially licensed by the Grammy winning star and doesn’t include any special access, on their own.

Here is what I can divulge: following the Washington Square Park portion of the trail, during which the guide revealed to me that Swift received an honorary degree from nearby New York University and delivered a commencement speech at the park during a 2022 graduation, we walked towards Electric Lady Studios, the Greenwich Village studio commissioned by rock legend Jimi Hendrix. 

Swift recorded a number of her most famous albums here, including Lover, Midnights, Folklore, Speak Now (Taylor's Version), Red (Taylor's Version) and Fearless (Taylor's Version).

Taylor Swift walking tour of NYC
Photograph: GetYourGuide

Although absolutely freezing and a bit annoyed about the fact that we couldn’t even take a peek inside the legendary music venue, it suddenly dawned on me that… I was enjoying myself? 

A New York resident for nearly 20 years whose job heavily relies on criss-crossing town in the hopes of discovering all things new and cool, I sometimes forget about the beauty and very New Yorkness involved in a simple walk for the sake of walking. Given the fact that the tour doesn’t involve actual access to the various Swift-adjacent destinations, the experience ends up turning into a stroll through a pretty hefty section of downtown Manhattan, indirectly morphing into a love letter of sorts to the various neighborhoods visited. I couldn’t really find my inner Swiftie on the tour, but I certainly rediscovered my intense passion for some of the sites that make the city so special—including The Stonewall Inn, where Swift performed a surprise concert in 2019, and the townhouses that pepper Greenwich Village, one of which Swift famously rented. 

Turns out, Swift actually does add to New York’s charm.

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