500 miles from St. Paul
I'm going on a little road-trip with three other guys next week and we have no specified destination. Our only rules are 500 miles(one-way) and that we want to eat at a lot of old-school diners and eateries. On the interstate or off doesn't matter much.
What do you have for us?
Hmmm... well, you could go south through Iowa to the Quad Cities. Along the way you would go through Mason City, Waterloo, Cedar Rapids and Iowa CIty. I don't know many places in those cities, though my parents always stop for the rinderwurst in Denver Iowa at the Denders (?) grocery store. Then, in the Quad Cities you could go to Lagomarcino's which is a confectionery/ soda fountain from the turn of the century, the Belgian Village from the 1970s (famous for their reuben) and a Maid Rite. There is also Whiteys Ice Cream from the 1930s. On your way back to Minnesota you could go through Wisconsin instead of back through Iowa. Again, I can't think of old-school places along that route but I'm sure there are plenty. Outside of Milwaukee there is a place called the Apple Holler - it is a restaurant on a farm. The farm has been around for a while and the restaurant is "home cooking style".
I've spent a lot of time in the Quad City with family, so I happen to know of these places. I've never thought of the QC as a big destination area, but if you can find other stuff along the route it might make a fun trip.
I would head to my home state of Iowa. Decorah has the best cinnamon roll I've ever eaten, at Ruby's on main street. Then, get a good map and work your way to the Irish Shanti in Gunder for one of their gigantic cheeseburgers http://www.essentialiowa.com/gunderbu...
with hash browns on the side. From there, it's on to St. Olaf for what is arguably the best tenderloin in Iowa. Iowa City is a good food destination and the Hamburg 2 is a terrific diner. The pie shakes there are legendary. There are lots of Iowa City threads on the board. I would follow this up with a trip to West Liberty for some terrific Mexican food. Then I would go to Kalona, an Amish community, and make a stop at the bakery there. I love their chocolate chip cookies. If the sale barn is holding a sale on the day you are there, stop by for a great homemade lunch. I love the hot beef sandwiches. Then, head to the Quad Cities. I could go on and on but that's a start.
17455 Gunder Rd, Elgin, IA 52141
Have you thought of doing the reverse "Feasting on Asphalt" that Alton Brown did this summer? Head south for 500 miles down the river road. You should be able to find plenty of diners in the small towns that you pass through along the way. You could head down the MN/Iowa side and return on the IL/WI side. Just a thought. We're in La Crosse, and it's certainly beautiful around here. (You wouldn't be tied to an Interstate, either.) La Crosse is a FUN town, too!
I think I would try for Cincinnati. It's about 700 miles and with 4 guys that's no problem. Great place for dive diners with the weird chili they have there. Plus you could hit Milwaukee and Chicago on the way. Otherwise if you want to go less than 500 miles Chicago and Milwaukee are your best bet. St. Louis is just over 500 miles. You could get Iowa made rites on the way and ribs once you are down there.