The strangest thing about Boston is watching a sales person at one of the smaller audio shops stand next to some $12K pair of speakers and say that their shop is NOT really a high-end audio shop.
The biggest shop in-town is Speartsound (solid state mostly) I think they're the biggest Krell dealer. They have rows of B&W, Dali, Theil speakers lined up all around the the walls.
Goodwin's Audio (uh, is that what $125K wilson speakers look like!) you may have to wait to get into one of their listening rooms. Make an appointment.
I'd check ahead for acts playing at Scullers or Regatta Bar in that order.