This weekend is the 30th annual Artscape, the largest free arts festival in the country and the pride of Baltimore. I've gone to the festival with my kids each of the past three years (that's Jack, left, taking in the art cars a couple years ago) and have gained some valuable insight. My advice:
1. Go early in the day when the crowds are smallest.
2. Just mosey around. You won't go far before you run into something interesting. If you try to get to everything, you will lose (this is my nature I'm always fighting it).
3. Scout out a good place to sit and eat. Every year we seem to end up perching on some random sidewalk or traffic median and gulping down our chicken kebabs.
Every time we go, I get a little overwhelmed by the crowds and the scope of the festival, which this year includes three stages, 175 tents and more that 4 million square feet of exhibit space. I still have nightmares about the Artscape two years ago when I took my two boys—one 8 months old—in the middle of Satiurday afternoon, solo, on the packed light rail. Never again. (Though I do recommend taking the light rail, just not alone with a infant and a toddler).
There a ton of attractions for kids tihis year. The art cars are a great attraction for all ages, while older kids will probably not want to leave the new Gamescape, though they'll probably also really dig the new Rabbit Hole exhibition. There are a bunch of really great family-friendly shows, including magic, hula hoops, and acrobats, and, as in years past, Target is sponsoring a giant area with arts projects for kids. But you'll do just as well just wandering, people-watching, finding cool random artists or shows. It really is a wonderful event. Have fun!