Which Jazz Albums are similar to Kind of Blue

relaxin' (miles davis)
crescent (john coltrane) - and, if you like that: 'alternate takes' and 'my favorite things', also by coltrane

Don't know if you are enamored by Miles' style of play or genre of jazz. As far as style, check out Howard McGhee, Clifford Brown and Chet Baker for similar styles of playing with a coolness.

As far as era of music it is endless with some of the top players being Ben Webster, JJ Johnson, Bill Evans, Sonny Criss and a cast of hundreds. You might find some samplers of jazz from labels such as Blue Note, Pablo and Concord Jazz.

If you have a decent public radio station with evening jazz programming, that can be a great source for information.

"Boss Tenor" - Gene Ammons
"A Love Supreme" - John Coltrane

the Cannonball Adderly album is a good suggestion.

I would also highly recommend two albums by Bill Evans (the pianist on most of Kind of Blue): "Waltz for Debby" and "Sunday at the Village Vanguard" (in that order). Awesome albums, and I think you will find them extremely enjoyable.

Check www.allmusic.com for info.

Just a follow up to Celtic66's suggestion about finding a public radio station with an evening jazz show. Our local station has Bob Parlocha's show. His selection is quite good and he gives you thorough info about each set of songs; names of songs, performers, labels and more. I have found leads to some good albumns from him. You can also go to his website.
jazzwithbobparlocha.com