S and her parents work at the Me and Thee Coffeehouse in Marblehead, MA (it's 30-45 minutes from Boston depending on how you go). I go every now and then and catch the shows I find interesting. There are a few venues in the Boston area that have a solid concert list and Me and Thee is one of them. For example, in the next few months they have Ellis Paul, Antje Duvekot, and Lucy Kaplansky.
Definitely worth checking the concert schedule to see if there are upcoming shows you might be interested in. It's a great venue and when J is there, they have amazingly decadent cookies.