My work takes me across the Dakotas, Nebraska, Iowa, and Minnesota. Sometimes small to medium cities, sometimes small towns and byways. I usually have a night or two to look around.
I think I'm good at looking around. Wherever I am, I find something interesting. This is what I do.
If I have a long drive, which for me is more than 3 hours because I am a driving-wimp, I point Google Maps at a non-chain coffee shop in a town along the way. A town with a good coffee shop, especially with a bike path, is almost always interesting.
If I'm not flying I take my mountain bike (in winter I take skis). For much of the year I can get an hour or two of riding. In town I pick a spot in Google – usually a local attraction. Bike trails go by the good stuff. I put my phone with the volume turned high in the top compartment of my hydration pack; I can hear the voice pretty well. I orient myself by the sun, then I set out. I look for interesting streets and parks. With the mountain bike I can cross woods and grassy areas. I let the voice guide me but I don't follow it directly; I can usually find a more pleasant route than Google's default bicycle directions.
Lastly, during each trip I'll do at least one night as a drop-in at a local CrossFit gym. I email ahead to confirm the date is good. I meet local people with a shared interest — they often have good advice on places to go.