You’ve mastered Bloomington 101, heading down for a game or a show and driving back up 37 late at night. It’s time to graduate to a higher level of B-town appreciation and spend a weekend in the state’s coolest community. You’ll need a full afternoon to explore the on-campus Sidney and Lois Eskenazi Museum of Art (1133 E. 7th St., 812-855-5445). Famously designed by I.M. Pei in 1982, it just reopened after a three-year, $30 million makeover created more gallery space, a conservation lab open to the public, and a skybridge that was part of Pei’s original design but never built until now. Find the Picassos and the Pollocks, then grab a bite in the lovely light-flooded cafe.

You could simply pop by another new attraction—the Graduate Bloomington hotel ($159/night; 210 E. Kirkwood Ave., 812-994-0500)—because it has the feel of a student union, drawing in townies and gownies alike to hang out in the cafe and communal workspaces. But checking in is better than just checking out the hip digs for a few minutes. It’s like a funhouse of Indiana cultural references, including basketball hoops as light fixtures and a Jack & Diane Terrace. There are too many nods to count, but one you can’t miss is the huge display of cookie jars in Poindexter’s restaurant, an homage to the world-record collection in Metamora; look for the jar your grandma had.

Now that you can afford more than Dagwood’s subs, have dinner and cocktails at Cardinal Spirits (922 S. Morton St., 812-202-6789) and see what Dean Wirkerman, a chef with Culinary Institute of America credentials and training at Per Se in New York, is cooking up. Bloomington has a nationally renowned comedy scene, and Alex Moffat from Saturday Night Live headlines January 16, 17, and 18 at The Comedy Attic (123 S. Walnut St., 812-336-5233). You won’t feel too old at the Social Cantina (125 N. College Ave., 812-287-8199), an upscale bar with 135 choices of tequila.

Hungover or not, you’ll benefit from some quiet time at the Tibetan Mongolian Buddhist Cultural Center (3655 S. Snoddy Rd., 812-336-6807). Take a walk around the 90-acre rural property and find the Buddhist monuments. Then spend an afternoon shopping on the courthouse square. At The Book Corner (100 N. Walnut St., 812-339-1522), pick up a tote bag with a map of independent booksellers around Indiana; each place offers a pin meant to be attached to the bag. Gather (116 N. Walnut St., 812-287-8046) has the hip-and-handmade market cornered., and Andrew Davis Clothiers (101 W. Kirkwood Ave., 812-323-7730) has a serious designer-shoe collection. Get a from-scratch Nutella hand pie and macchiato from The Inkwell (105 N. College Ave., 812-822-2925) for the drive home. And rub that stamp off your hand.