Aimless drives are great...but when I have so many goals including route-marker photos, county clinching, and highway clinching, I almost always orient my road trips to include those goals. I don't like retreading the same ground or backtracking, when I can explore someplace new. Exploring new ground in your vicinity becomes more difficult when you've seen nearly everything within a given range of your home--this is true for everyone up to a certain range. It's harder for me to embark on an aimless drive that gets me new mileage or shows me something new, so covering new ground has to become a intentional, rather than aimless, at a certain point.
Going wherever you want serendipitously, making no decisions until the spur of the moment, might be the ultimate expression of freedom. I loved pursuing that expression of freedom in my late teens and early twenties (though I didn't have access to a car during my eight semesters of college). Usually my impromptu trips would be short-term, taking me to a locale just an hour or two away. My main objective has always been to snap photos of route markers. For example, I remember trying to photograph county pentagons in LaSalle County, the state highways in Lake County (why are there so many??), or something like that. One time, I left my job in Joliet and noticed a sky full of dark storm clouds and peeks of sunshine--recognizing this as a perfect scenario for rainbow formation, I used radar to find where I was sure the western evening sun would generate a rainbow. This random drive did successfully lead me to a rainbow--I found it all the way in Millington. (This is a safer storm-chasing scenario, than say, chasing a tornado!) As the storm kept changing, I had to keep changing course- I didn't know where the drive would take me!
Since 2014, I have had a bunch of road trips loaded in the chamber, and these road trips are planned to efficiently provide me with route marker photo ops or county clinches. When I get the chance to, I will determine which pre-planned road trip to execute, based on weather forecasts and the amount of time available to me. Despite the fact that these trips are planned in advance, they still feel freeing and fulfilling to embark on them. Though they aren't truly aimless, I'm still making a dream of mine come true, and that feels comparable to a truly aimless drive, I think.