There's actually quite a bit of fun to be found here when the weather's nice.
We've got "Festival," the first full weekend in June, which I've heard is the largest volunteer-run outdoor festival of its kind in the world. There are five stages of diverse live music acts, twenty-some food booths, and a rather large art tent.
Throughout the summer we've got the Wednesday-night bluesfest free concert series held at Rosa Parks' Circle (which turns into an ice rink whenever the temp. dips below 50º, and was designed by Maya Lin)
On the first full weekend of September there's Celebration on the Grand, with three full days of live local entertainment, plus a semi-big name band (Bowling For Soup, Mustard Plug in the recent past) on Saturday night followed by (oooh) fireworks. Also, there's a beer tent
Then in late September is the Eastown Street Fair, with three stages of live local music, inexpensive hippie crafts, and a few food booths.
So if you're down with the local music scene there's a fair bit of free entertainment during the summer. Of course, in the winter, it's far too cold to ever do anything (besides
ice skate), so we all just stay inside.
Oh, and there's a bigass tire swing in the middle of town. A source of infinite drunken entertainment.