Well, there's a few festivals in, or relatively close to, New England but with work, kids and other life factors it's hard to get out them. Plus, they're often wicked expensive. I wanted to go the the Joe Val Bluegrass Fest a couple of weeks ago but it was well over $50 for a Saturday day pass. Last summer I won tickets to the Grey Fox Festival which was cool. The other issue that I run into is that no one else around me listens to this stuff. I'll go solo to shows at places like the Iron Horse or at the Indian casinos in Connecticut if it's someone I really want to see. There it's easy enough to hang out with a coffee and something to read until the lights go out, and I almost always run into nice people.
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