The Weekly Dig is a free newspaper in the Boston area, released every Wednesday. It's very similar to the Village Voice in New York City.
The paper is heavily liberal, and aimed at the alternative community. It has reviews of local music, events, and beer-related stories. It has a very comprehensive daily listing of venues with music and film events - around 60 each night.
An unfortunate side-effect of the Weekly Dig's location is its heavy bias for Red Sox (and therefore against all that is holy).
Its comics are Too Much Coffee Man, The K Chronicles, Secret Asian Man (aka SAM), No Exit, The Thinking Ape Blues, and a weekly comic showcase. I heartily recommend The Thinking Ape Blues.
Its back pages are full of masseuse, escort, and phone chat line ads.