My mom's from woolstock, it's like a town that's literally like two blocks big near fort dodge and eagle groove. I went there for a family reunion a few years back, some dude was hammered on the corner and walk up to my mom and hit on her in like a total drunken stuper. And everyone was like oh don't mind Sam(or whatever his name was) he's just the town drunk. I was like that's hiliarious any place where everyone in the town identifies one person as "the town drunk" is a cool small town to me. I really didn't think small towns had town drunks, I just thought that was something you seen on the Andy Griffith Show.
Someone mentioned Dyersville. I moved here a year ago because it was the cheapest option for my commute. $350 for the lower level of a duplex. However, the town sucks. No one my age, more specifically, no women my age. Real conservative, real old, real Catholic. Thats Dyersville in a nutshell. Don't throw in the Field of Dreams because that sucker is so far out of town its almost in Farley.
If you go to Boone you can ride the on the Kate Shelley High Bridge. It's actually a pretty scenic ride hence the name "Boone & Scenic Valley Railroad".
I'm biased, but Jefferson has some cool features too. If you go up the Bell Tower you can see 8 little towns. Also Fort Dodge, IA has a really cool, and super old baseball field called Patterson Field that hosts ICCC Fall Baseball League game on Sundays in the fall. It used to host Semi-Pro games and Ozzie Smith played their once. It has the old-time baseball feel I loved playing on the field.
Patterson Field Link: Jerry Patterson's Patterson Field - Fort Dodge Iowa - Home of Youth and Amateur Baseball
Bell Tower: Mahanay Bell Tower – Jefferson, Iowa — Iowa Tourism