Miles Davis moved to New York City at just 18 years old to attend the prestigious Juilliard School of Music. But having grown up in all-black neighborhoods in St. Louis, Miles experienced something of a culture shock at Juilliard, where the predominantly white student body and faculty studied not jazz, but classical music. He quit after a year because “the shit they was talking about was too white for me.”

Despite his dislike of it at the time, Juilliard gave him the type of formal music education other jazz musicians lacked, and Miles credited his time there as contributing to the direction his music went. Juilliard eventually moved to the Lincoln Center, and the campus Miles attended became the home of the Manhattan School of Music in 1969.

In the late 1940s, there was no more happening place in America than the clubs that lined 52nd Street between Fifth and Sixth Avenues. The Onyx, Three Deuces, and Club Carousel, to name a few, were where Charlie “Bird” Parker and Dizzy Gillespie honed the next aggressive step in jazz’s evolution: bebop. At just 19, Miles Davis began playing with Bird as his regular side man.

The Street, as it was known to its patrons, became the focus of the NYPD, as cops would funnel heroin to musicians and club-goers so they’d have an excuse to stage raids. At the time, bebop was akin to gangsta rap; it was an aggressive black art form that was both hated and feared by the white establishment. Walking down this section of 52nd Street today is a solemn experience; 21 Club is the only remaining venue, and it bears little resemblance to its past.

If the Street was where musicians went for exposure to white audiences, Minton’s Playhouse in Harlem was the “black jazz capitol of the world,” where the real development and experimentation of bebop took place. After the clubs on The Street closed for the night, musicians would head to Minton’s and play until the sun came up. Bands led by Bird and Dizzy would invite people from the audience up to play, like an audition. Fail the audition and you were likely to be booed off stage, or even assaulted.

When they invited Miles up for the first time, Bird and Dizzy were left smiling. “From then on I was on the inside of what was happening in New York’s music scene,” Miles said of that first performance. Minton’s has closed and reopened a few times over the years, and has been remodeled, but it remains to this day.

Cafe Bohemia started when the owner wanted to give Charlie Parker, who lived across the street and was hopelessly addicted to heroin, a platform on which to rebuild his life. Parker died before ever playing there, and instead, Cafe Bohemia became the venue at which Miles put his life back together, following his problems with the drug.

Cafe Bohemia is where Miles and John Coltrane, then completely unknown, began working together, and it was where the group now known as the First Great Quintet—Miles, Coltrane, Red Garland, Paul Chambers, and Philly Joe Jones—first played together in July of 1955. It was the backdrop for Miles’s recordings with Prestige, highlighted by the quartet of Walkin’, Relaxin’, Steamin’, and Cookin’. In short, this venue is where Miles Davis found his greatness. Today, Cafe Bohemia is a sports bar that makes no mention of its storied past.

Signing with Columbia Records gave Miles the resources to produce what would become widely considered the greatest jazz albums of all time, which were recorded in Columbia’s iconic 30th Street Studio. Kind of Blue (1959), Miles Ahead (1957), and Bitches Brew (1970) are just some of the masterpieces Miles recorded in the studio, where he and long-time producer Teo Macero would famously spar over the best path forward on any given tune. His time in the studio began in 1957 when he recorded the straight-ahead jazz album Milestones, and ended in 1972 with the jazz fusion classic On the Corner.

Miles was hardly the only musician to make history in the studio, as Glenn Gould’s Goldberg Variations, Pink Floyd’s The Wall, and Leonard Bernstein’s West Side Story were also recorded there. Columbia abandoned the studio in 1982. It has since been demolished and replaced with a luxury apartment building.

The commercial and critical success of his early albums with Columbia made Miles rich and famous beyond his wildest imagination, and with his earnings he purchased a five-story Russian Orthodox church on the Upper West Side and converted it into a home. In the basement, Miles built a gym and music room, where he could practice without disturbing everyone else in the house, and it was the scene of many brainstorming sessions and rehearsals with other musicians. His wife Francis and their four children lived in the building as well, and they rented out the top two floors.

During his retirement years in the late 1970s, the house became the dank, smokey setting of Miles’s squalor, a period during which he succumbed to heavy drinking, cocaine use, and womanizing. After his death, the home was split into six separate units. In 2016, one of the units sold for $500,000. That strip along West 77th Street is now called Miles Davis Way.

The Village Gate opened in the late 1950s around the same time the Vanguard switched to jazz. While Miles didn’t get as much use out of the Gate as the Vanguard, it worked its way into his regular touring rotation, particularly later in the ’60s when Miles was working with the Second Great Quintet. Following John Coltrane’s death in July 1967, Miles booked the entire month of August at the Village Gate, and in his autobiography he says those performances became “the talk of New York,” as celebrities packed the venue.

Miles also played regularly at the Gate during his electric period in the late 1960s and early 1970s, having Richard Pryor open for him once. The building at 160 Bleecker has a long and interesting history, and while the original Village Gate closed in 1993, its sign still hangs on the building. Today, the performance space is now (Le) Poisson Rouge.

Miles Davis was a man who took things to extremes, and it was no different when he was on one of his health kicks. His favorite workout was boxing at Gleason’s Gym in the Bronx, where legends like Muhammad Ali trained. In the late 1950s and early 1960s, Miles was the model of health, training at Gleason’s for hours at a time. He had periods where he ate as a vegetarian, having said in 1969: “I figure if horses can eat green shit and be strong and run like motherfuckers, why shouldn’t I?”

Gleason’s Gym moved to West 30th Street in Manhattan in 1974 and to DUMBO in 1984, where it remains to this day. Over the years, its locations served as sets of a number of movies, including Raging Bull.

Miles Davis took great pride in how he looked, rocking impeccable Brooks Brothers suits in the 1950s and looking very much the part of the rock star he wanted to be in the 1960s and ’70s. Part of his showy style included a taste for expensive Italian cars, which he could often be scene driving along the West Side Highway.

But this also got him into trouble: 1972, he wrecked his lime green Lamborghini Miura on the West Side Highway at 125th Street, totaling the car and breaking both his ankles. A passerby on the scene said he was covered in blood and cocaine, and you could see bones coming out of his pants. The wreck ended up being something of an end of an era for Miles. He suffered from intense chronic pain in the following years, which contributed to his decision to retire in 1976. Though he returned in the 1980s, his post-retirement work didn’t have the same impact.