Help me find a rad Midwest city to live in

-38/yo single male originally from Iowa

-Self employed and work remotely

I'd like to find a smallish, hip city (probably in the Midwest) that has the active/academic Boulder, Madison, Asheville vibes with a lower cost of living.

I love to commute via bicycle and could probably only afford a house/condo around the $200,000 - $250,000 range.

If you could live anywhere, were from the Midwest, and you're making around $7k/mo, where would you go to meet cool people into doing the same things? TIA.