Where to go: South Dakota

Three years ago I would’ve recommended Pee Wee’s Mountain Music Show. But Pee Wee died and I think they shut it down. Too bad, because it was friggin’ fantastic!

I would recommend traveling through Needles Highway, as you can park your car, get out and climb away. (From I-90 and Rapid City, take Highway 79 south about 18 miles, then Highway 36 and 16 southwest about 20 miles until you reach Highway 87, the Needles Highway.)
Also, in the Black Hills, as far as kitchy goes, there’s The Cosmos:

(From here)

Happy, who spent every other summer there growing up

Well, if you’re leaving from Minneapolis, MN, contingent on the route you can stop in Darwin, MN for one of the world’s largest balls of twine which is right out US Highway 12 towards SD.

If you get into the Hot Springs area, hit Evans Plunge to cool off (a natural spring–all indoor) and also make a trip to the mammoth site. You can see a mammoth dig in progress.

For Kitsch, Wall Drug is great, but you might also hit Keystone (near Mt. Rushmore). They have a bunch of touristy little shops–good place for souvenirs for the kids.

I grew up in Rapid City. I can’t say I miss living there (few job opportunities, backward politics, etc), but I miss the Black Hills. It’s a beautiful place. Have fun!

I haven’t seen many mentions of places to stay, so I’ll just toss this one out. My wife and I spent a night in a nice little B&B outside of Deadwood called Black Hills Hideaway. Don’t know if it is in your price range or not but it was sooooo nice. I highly recommend it.