Walking in Bob Dylan’s Shoes in New York City

For more than 40 years, Greenwich Village record shop owner John Pita has had a window on Bob Dylan history.

He owns The Record Runner store, which faces the single block of Jones Street where Dylan was photographed walking arm-in-arm with his girlfriend and muse Suze Rotolo on a snowy February day in 1963. The photo became the cover of Dylan’s second album, The Freewheelin‘ Bob Dylan, and a pop culture calling card for one of New York’s most historic and fascinating urban neighborhoods.

Since James Mangold’s biopic A Complete Unknown received eight Oscar nominations in 2025, including one for Timothée Chalamet’s performance as Dylan, another generation is discovering the legendary singer-songwriter and Nobel laureate.

The Bob Dylan New York City Tour

Visitors can find traces of Dylan in the Village through the places where he lived, wrote, and performed in the early 1960s.

“They come all the time,” says Pita of Dylan devotees who want to have their own Freewheelin’ moment. He keeps an empty record sleeve handy for a prop. He has a well-thumbed file folder with close-up images and photo shoot outtakes that show the spot where the record cover image was taken. 

Most people get it wrong, Pita said. Aim for the manhole cover just down from the Florence Prime Meat Market — opened in 1936 — and you’re close.

Record Running has dozens of Dylan records among the rows of jammed bins in the small store. There’s also the movie soundtrack featuring Chalamet.

The Before Times in Dylan’s New York

The Village has changed over the 64 years since 19-year-old aspiring musician Dylan arrived from Minnesota, hoping to connect with his idol, Woody Guthrie. Over 100 years of Bohemianism have faded, and the counterculture has gone mainstream.

Most of the coffee houses and clubs of Dylan’s era have been replaced with high-priced real estate, restaurants, and boutiques. That’s why Mangold shot A Complete Unknown in more 1960s-looking locations in neighbouring New Jersey.

Yet Greenwich Village’s ties to Dylan remain strong, and places still evoke that freewheelin’ spirit.

Whether you’ve never heard “Blowin’ in the Wind” or you’re a Dylan devotee, the single square kilometer of the Village is a good choice for a lazy exploration on foot in a green and tranquil patch removed from the New York bustle.

The neighborhood breaks from Manhattan’s regimented grid street pattern. Narrow cobblestone roads lined with brownstones and heritage houses twist, flow, and turn back on themselves like the rivers they once followed. It’s common to see tourists squinting at their phones, trying to figure out directions. Getting lost is part of the experience. 

To help, download a free map for DIY Dylan walking tours. The Greenwich Village Society for Historical Preservation has a good one. 

Ain’t Talkin’, Just Walkin’ 

Better yet, book a walking tour, like the two-hour one I took with professional guide Jordan Friedman. The Dylan fan and longtime Greenwich Village resident leads private walks with ToursByLocals.

Friedman told us that Greenwich Village could be called “the ultimate influencer” for its role in shaping modern culture. The 1911 fire at the Triangle Shirtwaist Factory led to labor laws and safety regulations. A few blocks over, the Stonewall Inn was the birthplace of the LGBTQ rights movement in America and is home to the Stonewall National Monument and visitor center.

“It is like a village still, as much as it used to be,” said Friedman as we started at the gated entry to Washington Mews. It was originally a trail used by Lenape indigenous people to travel between the Hudson and East rivers. The street is lined with 19^th-century carriage houses built for the row of Greek Revival townhomes a block south, facing Washington Square Park. 

The Scene at Washington Square Park

The park is where Dylan comes in. Enter the green space through the marble Washington Square Arch, modeled on the Arc de Triomphe in Paris. Dylan often hung out here, strumming his guitar near the Tisch Fountain. It’s a scene that continues, Friedman says. It’s still a popular meeting spot and hangout, especially on a sunny day, where chess players wait at set-up tables for opponents to join them.

Washington Square was also the site of a Chalamet look-alike contest last fall, where the star surprised fans by showing up out of the blue.

It’s also name-checked in the Joan Baez song “Diamonds and Rust,” which she composed after her breakup with Dylan. It includes a reference to their room in “that crummy hotel over Washington Square.” 

That Crummy Hotel

The circa-1905 hotel was called the Hotel Earle back then and had flophouse vibes when Dylan stayed there in 1961. Two years later, he and Baez shared room 305, which has what Friedman calls “a New York view.” The window looks out on a brick wall.   

Far from its crummy days, the renovated Art Deco-style hotel today has a chic dining room and rooftop garden. 

It’s proud of its deep music history. Canadian folk duo Ian & Sylvia wrote “Four Strong Winds” there. Michelle and John Phillips composed “California Dreamin’” while staying at the hotel. The Rolling Stones made it their base for their first U.S. tour. 

And then there’s Dylan. 

When guests request 305, hotel manager Marta Bukala recommends a room with a better view. But Dylan diehards won’t be dissuaded. “Somebody asked for room 305 when they were on their honeymoon,” she said.

Around the Neighborhood

We stopped outside a red brick walk-up at 161 West 4^th St. to see where Dylan and Rotolo lived in an apartment on the fourth floor at the rear. Jones Street is kitty-corner, a block down. The Music Inn is across the street. It’s still packed with instruments and record bins, much like when Dylan frequented the store.

A block from Washington Square is MacDougal St. Dylan played for the first time in New York at Cafe Wha? at 115 MacDougal. It’s still in business, and there’s live music by a house band on most nights. 

The Bitter End, Dylan’s haunt on nearby Bleecker Street, also remains open. Look for the distinctive blue awning. 

There’s no longer music at Café Reggio at 119 MacDougal St., where Dylan played. But you can get a great cup of coffee at the place that claims to have served the first cappuccino in the U.S. in 1927. 

Where Dylan Did Drugs

Dylan likely visited the neighborhood drugstore, C.O. Bigelow Apothecary, on 6th Avenue. It’s a local landmark with its vertical red neon sign, original chandeliers, and towering glass display cases. It has been dispensing medicines since 1838.

Alec Ginsberg, the 33-year-old fourth-generation owner, said famous locals from Mark Twain to Lou Reed and David Bowie picked up prescriptions there. So did artists recording at nearby Electric Lady Studios, which was commissioned by Jimi Hendrix in 1968.

“I’ve been listening to Bob Dylan since I was born. Like, obsessively,” Ginsberg said. He’s a fan of the movie, saying people who initially went to see Chalamet onscreen could end up turned on to Dylan’s music. 

The Legendary Chelsea

Dylan also had ties to Chelsea, the neighborhood just north of Greenwich Village.

The magnificent Victorian Gothic-style Hotel Chelsea, built in 1884, also appears onscreen in A Complete Unknown. Dylan stayed in room 211, now room 2A, in the early ’60s, where he wrote songs for his 1966 album Blonde on Blonde. 

The Chelsea is part of so many stories of the legendary poets, writers, artists, and musicians who stayed and created there over the years that it’s earned cult status.  

Now an eclectic luxury hotel, room rates start at about $500 per night. But you can look at the lobby or soak up the atmosphere in the Café Chelsea, Lobby Bar, or El Quijote Basque restaurant.

Dylan fan and musician William Benton is a doorman at the Chelsea who rocks a cool look that speaks to his first days hanging out there as a teen.

Growing Interest in Dylan in New York City

He doubles as historian and guide, taking hotel guests on free tours into the heart of the Chelsea’s past, including Dylan’s time there. He’s seen a slight uptick lately in people asking about Dylan. However, more visitors seem keen to know about musician Patti Smith and photographer Robert Mapplethorpe and the stories of their time at the Chelsea in her award-winning memoir Just Kids.

Still, Benton was pleased to hear Blonde on Blonde cuts on the sound system in a MacDougall St. bar recently, as the young bartender commented over a game of pool that Dylan was “cute.”

Was she talking about Bob or Chalamet?

“The movie made me curious,” Benton said, admitting he wasn’t a fan of the film, which he found followed a too-predictable biopic path. “I just saw Dylan (perform) a couple of months ago. What would it be like if this did energize a new generation?”   

If you go   

Stay 

• The Washington Square Hotel, 103 Waverly Pl. 
• The Hotel Chelsea, 222 W 23rd St.  

Where to eat 

Several great pizza joints in the Village were open when Dylan lived there. 

• Dine in at John’s of Bleecker Street (278 Bleecker St.), which opened in 1929. 
• The circa-1880 White Horse Tavern, 567 Hudson St., was a Dylan hangout.

Take a walking tour   

• TourByLocals, toursbylocals.com 
• On Location Tours offers A Complete Unknown tour.  
• Download a free map for a DIY Dylan walking tour from the Greenwich Village Society for Historical Preservation.

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Linda Barnard is a travel writer from Victoria, British Columbia. Read more about her work on MuckRack and see her portfolio. Follow Linda on Instagram at @barnardwrites