The Bride and I found
New Harmony, Indiana to be pretty charming with a couple of decent restaurants and a nice hotel. You have to like visiting Utopian communities and some interesting new and old buildings, and it is a pretty long drive, but I think you might be able to combine it with a leisurely run down the Wabash to make a weekend of it.
Only went once, but we have always wanted to go back. Really a lovely and fascinating place.
Edit: You need to go to the website of the New Harmony Inn and Conference Center to find the nicer restaurant attached to the Inn. We stayed at the Inn and enjoyed it. The food, on the whole, is good but nothing that interesting or wonderful, just so you know. Better than average Illinois/Indiana downstate and with some pretensions when we went almost 10 years ago.
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Feeling (south) loopy