The arrival of a new 5-CD box set Springtime in New York has a lot of music lovers talking about another chapter in Bob Dylan’s phenomenal career. It may be the perfect time for locals and out-of-town travelers to take a first-hand look at the New York sites that are an integral part of Dylan’s history.
America’s greatest songwriter left Minnesota at age 19 and arrived in New York City in an Impala sedan with nine inches of snow on the ground in January 1961. He was on a mission to find his idol Woody Guthrie.
On the day of his arrival, he performed at the Cafe Wha? at 115 MacDougal St. in Greenwich Village, according to June Skinner Sawyers’ book Bob Dylan New York. The cafe still operates nightly as a music club.
Sawyers and Peter McKenzie, who was 15 when his family allowed the newly arrived Dylan to live in their Manhattan apartment, serve as this article’s tour guides to other sites. McKenzie recently released a new book about those days, Bob Dylan On A Couch & Fifty Cents A Day.
Dylan began frequent visits to the McKenzies in March 1961 and moved into their apartment at 10 W. 28th St. in mid-May. He slept on the living room couch except for three weeks when McKenzie went to summer camp, and Dylan occupied his bedroom. No members of the McKenzie family live there now, and the apartment building is a private residence.
At Gerdes Folk City on April 11, 1961, Dylan played his first professional gig, warming up for blues giant John Lee Hooker. The legendary club was located at 11 W. Fourth St. in a building that no longer exists and moved to 130 W. Third St. in 1970. Citing rising rent, the club closed in March 1986.
Dylan lived with the McKenzies until mid-September 1961, when he moved out before a performance at Gerdes on Sept. 26, 1961. The New York Times reviewed the show, calling Dylan “a cross between a choir boy and a beatnik” and applauding his “music-making originality and inspiration.”
A month later, Dylan signed a recording contract with Columbia Records, and, on Nov. 4, he played a concert at Carnegie Chapter Hall on the fifth floor of Carnegie Hall. The notable venue at 57th Street and Seventh Avenue ordinarily offers public tours, but they are temporarily cancelled because of the pandemic. Prospective vistors can sign up on the hall’s website for notification when tours will resume.
The McKenzies attended the Carnegie Hall performance and then saw Dylan less frequently.
“He would come back and visit on a regular basis over the next two years either to just say hi or seek advice from my parents about what was going on with his life,” says Peter McKenzie, who left New York to attend Harvard University in September 1963. “Naturally, the visits became less and less as the business of his schedule increased and the more famous he became. And then, of course, he got married and started his own family.”
Dylan enjoyed hanging out in Greenwich Village’s Mills Tavern at 158 Bleecker St. where he talked and drank with the Clancy Brothers and other performers, McKenzie says. The tavern and the Mills House, a 1,500-room 1896 hotel, no longer exist there, and a namesake pub has moved across the Hudson River to Hoboken, New Jersey. An apartment building now stands at 158 Bleecker St., and the letters “Mills House” are over the front door.
Two other Greenwich Village addresses are Sawyers’ favorite Dylan sites: 161 W. Fourth St. and 169 W. Fourth St.
“The apartment where he and (his girlfriend) Suze Rotolo once lived was at 161 W. Fourth St.,” Sawyer says. “I get a kick knowing that the building still exists and imagining what it must have been like to have been there, lived there during that era. The Music Inn at 169 W. Fourth St. is a leftover from the folkies’ Village scene. How can you not love that, especially in a world that is constantly changing?”
The owner of the Music Inn, a shop selling instruments and records since 1958, considered Dylan annoying, according to Sawyers book, because he came into the store to see if his records were for sale and never made a purchase.
Sawyers enjoys visiting the coffeehouses on Macdougal Street near Bleecker Street, especially Caffe Reggio and Dante. Dylan performed at the Caffe Reggio, which was established in 1927 and claims it’s the first U.S. cafe to serve cappuccino.
“Going to Reggio is like returning to some kind of 20th-Century time warp,” Sawyers says. “Every time I’m in New York, I try to go there.”
Dante, at 79-81 MacDougal St., was called Caffe Dante when Dylan was a customer and lived in a townhouse across the street. Other famous customers included Ernest Hemingway, Al Pacino, Robert Maplethorpe, Patti Smith and Jerry Seinfeld.
The cover of The Freewheelin’ Bob Dylan, his brilliant second album released in 1963, shows Dylan walking down Jones Street in the West Village with his girlfriend Suze Rotolo. The photograph was shot in February 1963 at the corner of Jones and West Fourth streets, a perfect location to visit and remember the album which includes such classics as “Blowin’ in the Wind,” “Girl from the North Country,” “Masters of War,” “A Hard Rain’s A-Gonna Fall” and “Don’t Think Twice, It’s All Right.”
In her memoir, Rotolo wrote that the photo “is one of those cultural markers that influenced the look of album covers precisely because of its casual down-home spontaneity and sensibility.”
The 12-story Chelsea Hotel, where Dylan, Smith, Mark Twain and many other musicians and writers lived, should not be missed on West 23rd Street, Sawyer says. Dylan and his wife Sara lived there when she was pregnant with their first child, Jesse. The 19th-Century Victorian Gothic hotel was bought five years ago by BD Hotels for $250 million and is being renovated.
“It may not be the bohemian Chelsea Hotel of old, but it is still an iconic New York building full of all kinds of literary, artistic and musical ghosts,” Sawyer says. “It’s a magical, weird, surreal, gritty place.”
Dylan’s debut album and his classic 1960s albums The Freewheelin’ Bob Dylan, The Times They Are A-Changin’, Another Side of Bob Dylan, Bringing It All Back Home and Blonde on Blonde were recorded in Columbia Recording Studios’ Studio A at 799 Seventh Ave. The building was demolished in the 1980s, and the AXA Equitable Center stands on the site at 51st and 52nd streets.
In April 1983, Dylan brought five renowned musicians — Mark Knopfler, Mick Taylor and Alan Clark from England and Robbie Shakespeare and Sly Dunbar from Jamaica — into the Power Station studios at 441 W. 53rd St. The musicians recorded songs for Dylan’s Infidels album, including “Jokerman,” “Sweetheart Like You” and “Don’t Fall Apart on Me Tonight.”
The Maysles Brothers filmmakers documented some of the recording sessions for Infidels, but the footage at the Manhattan studios was never officially released. Now, in conjunction with promotion of the new Springtime In New York album, a restored video for “Don’t Fall Apart on Me Tonight” is available to view below.
Before the studios were built, the site was a power relay station for an electric company. Today, the studios are called the Power Station at BerkleeNYC, and they serve as a recording and video production facility and a campus for Berklee students.
Many New York City concert venues play an important role in Dylan’s musical history, with Madison Square Garden, on Seventh Avenue between 31st and 33rd streets, at the top of the list. Dylan performed many notable shows there, including a surprise appearance at George Harrison’s Concert for Bangladesh in 1971, a benefit for imprisoned pro boxer Rubin Hurricane Carter in 1975 and a 30th anniversary concert featuring numerous top musicians in 1992.
This short tour only mentions some of the many Dylan-related sites in New York City, so a future sequel is due. Dylan and his family left the city in the late 1960s and settled in Woodstock, New York, about 105 miles north of midtown Manhattan.
Since 1979, he has lived west of Los Angeles in Malibu. In 1988, he began his so-called “Never Ending Tour,” playing numerous concerts annually at venues worldwide. The pandemic halted the Never Ending Tour, but next month, on Nov. 2, the 80-year-old troubadour kicks off a 21-concert tour in Milwaukee.