My husband and I went on the Chicago Food Planet Near North tour last Halloween weekend and thought it was great, www.midwestweekends.com/plan_a_trip/s...
It was a tasting tour but with a lot of historical/cultural/architectural commentary -- our guide was extremely knowledgeable and entertaining. We were among the few tourists -- most of the others lived in the Chicago suburbs, and one pair lived in Lincoln Park.
I've also been on the Taste of the Neighborhoods tour with Evelyn Thompson -- she's a hoot! That stops at three restaurants, so there's more food, but also tons of cultural commentary. I recommend both of them. There's also the Tastebud tour, three pizza tours and a chocolate tour!
We tried to do part of the chocolate tour on our own, but unless you work hard to ask questions and engage the storekeepers, you won't learn nearly as much as you would on a tour.

Stephen Larson and Lisa Flicker gave up their Gourmet's Garden B&B and cooking school because people just wanted to eat their food, rather than learn how to make it. So they started Quarter/quarter restaurant in Harmony -- it's in the old Skandinavien Blomma/Clover Gallery shop.

Just drive around Lake Pepin -- it's 70 miles, with a good place to eat about every five miles. Our favorite dinner place is The Nortons in Red Wing, but lots of people like the Harbor View Cafe in Pepin, and then there's Vinifera in Wabasha and Nosh in Lake City. For snacking stops, the Smiling Pelican in Maiden Rock, Bogus Creek and Stockholm Pie Company in Stockholm, the Nelson Cheese Factory in Nelson and Rabbit's Bakery in Lake City, www.midwestweekends.com/plan_a_trip/t.... Good luck coming up with enough appetite to handle all that!

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Harbor View Cafe
314 1st St, Pepin, WI 54759

Rabbit's Bakery
304 S Washington St, Lake City, MN 55041

Bogus Creek Cafe
114 Spring St, Stockholm, WI 54769