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You should probably check out nuvo.net - it's Indianapolis's so-called 'alternative free weekly,' which lists a lot of things going on and things to do. Broad Ripple has a lot of meat-market bars that cater to the frat boys from nearby Butler, but Spin has some decent music going on sometimes, and the Vogue gets some good regional and national acts at times. The Brewpub and the Brugge Brasserie (sp?) are good places to hang out and drink some great handcrafted beers and maybe some food. Try the beer and cheese crock at the brewpub - it should please your Wisconsonian sensibilities.
The Melody Inn on Illinois north of 38th street has quite a bit of punk, post-punk, nuvo-hillbilly, etc. music going on. It's definitely out of the normal loop. If you really like music you should check out Indy CD & Vinyl on Broad Ripple Ave and Luna Music, which is just down College a bit. Both have a great collection of music and occasionally have in-store performances.
I don't get down to Mass Ave as much as I used to, but it has some galleries and a few cool clubs. Downtown is very tourist-oriented and it's full of chain restaurants that the conventioners love, but it's still worth a look. Check out the Fountain Square area southeast of downtown, which has a great music club called Radio Radio. At some point someone will suggest you go duckpin bowling and eat on the rooftop at the restaurant down there. You should do so. Hope that helps - I don't get out quite as much as I used to. Oh, and welcome to the 'nap.
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