Milestones (CL 1193) is a studio album by American jazz trumpeter and composer Miles Davis, recorded with his "first great quintet" augmented as a sextet. It was released in 1958 by Columbia Records.

Tenor saxophonist John Coltrane's return to Davis' group in 1958 coincided with the "modal phase" albums: Milestones and Kind of Blue (1959) are both considered essential examples of 1950s modern jazz. Davis at this point was experimenting with modes – scale patterns other than major and minor.

Davis plays both trumpet and piano on "Sid's Ahead," a blues which is reminiscent of "Walkin'." He plays trumpet in the ensemble passages and solos on trumpet but moves to the piano to accompany the saxophonists in Garland's absence. "Billy Boy" is a solo feature for Garland and the rhythm section.

Critical reception
In a five-star review, Allmusic's Thom Jurek called Milestones a classic album with blues material in both bebop and post-bop veins, as well as the "memorable" title track, which introduced modalism in jazz and defined Davis' subsequent music in the years to follow. Andy Hermann of PopMatters felt that the album offers more aggressive swinging than Kind of Blue and showcases the first session between saxophonists Coltrane and Cannonball Adderley, whose different styles "feed off each other and push each musician to greater heights." Jim Santella of All About Jazz said that the quality of the personnel Davis enlisted was "the very best", even though the sextet was short-lived, and that Milestones is "a seminal album that helped shape jazz history."

The Penguin Guide to Jazz selected the album as part of its suggested "Core Collection", calling it "one of the very great modern-jazz albums."