Nah never been. And only there til Tuesday. Sadly I couldn’t find any gigs of interest that worked. All in the days before and afterNowt like leaving me plenty of time for suggestions!
Well, baseball is over up there and I know the Pats are away this weekend, they play down here Monday night, so there's no sport for you (unless hockey is on - not sure). We stayed in Brookline and walked in, but that was because the venue was at the right end of town for us, right opposite Fenway Park. Brookline was a decent little neighborhood with a few bars and restaurants, a cracking little record shop (where I bought a Manchester Orchestra and a Fugazi single....and...ahem...a Tygers of Pan Tang album).To be honest we didn't do much else but drink and go to the shows each day! Went to McGreevy's which is the Dropkicks' bar - it's a pretty generic sports/Irish bar that claims to be the first ever "sports bar" (not really sure how they can make that claim) but the music was decent. That area looked ok too. Sam Adams and Harpoon are the main breweries up there but there's a lot of craft places now - we tried a few local brews - would imagine you can do tours and tastings.
Have you been before? Previous trips I've done the Freedom Trail - it's red brick line in the sidewalk that takes you around the key historical sites and that was really good (there are guidebooks that you can use that follow the same route and tell you about each stop - various burial grounds, Bunker Hill, where Paul Revere started his ride, Samuel Adams' house, old Ironsides (battleship), Faneuil Hall, etc. Trip up to Cambridge to stroll around Harvard - back in the 90s that was certainly a typical studenty area with bars, restaurants, record shops (Fort Apache studio is up there somewhere, but I was up there before smartphones and online maps so I couldn't find it, sadly - bloke I asked at a Cambridge record store was no help!).
I think they still do whale watching (and white sharks these days) out in the bay, but you'll be toward the tail end of the season for that, I imagine - I think I've done it early October before, but summer is best. There's a high speed ferry to Cape Cod (Provincetown) too.
How long are you there? I'm sure you saw The National are playing Thursday. For my tastes there's SLF, DIIV, Vivian Girls, and Against Me! in the next few days.
That's all I've got - not a lot to go on. Enjoy your trip.
cheers for the tips!