As the name gives away, you're going to hear a lot of Miles Davis at this place. Milestone is another classic jazz cafe perfect for when you have two hours to kill. Master Orito-san is a soft-spoken, kinono-wearing, really nice guy who keeps the vibe there mellow but swinging.
What really stands out about Milestone is the wall of books and magazines on the right side as you walk in. Although most are in Japanese, there are enough jazz photo books that even if you can`t read Japanese you can still spend a fun hour or so doing some browsing. Orito-san keeps the place open fairly late and there's booze on the menu so it's also a great spot for a few early drinks in the evening.
Takadanobaba is a "student town" so there's always a few college kid jazz fans in here, along with a few random salarymen. I spent a lot of my student days at Waseda University "studying" at places like this in Tokyo, and Milestone is one of the best.
Tokyo Jazz Joint photos of Milestone are here.
Station: Takadanobaba -JR/Seibu Shinjuku/Tozai Subway Lines
Exit: Waseda Exit
Distance from station: 4 minutes
Milestone is easy to find if you know where Ben's Cafe is; just look left before the Library for the Blind, and you'll see the sign on the right side. If it's your first time in Baba, come out of the JR station and turn right at the 'Big Box'. Head up the street and turn left on the street past Peacock supermarket. Walk down and take the right at the end of the street and walk up about 100 meters. Then on the left side you'll see a big grey building with odd chains on it; that`s the library for the blind. Milestone is easy to spot by looking left.