This was a day-hike in Oregon, Mount Hood National Forest, Tilly Jane Trail to Tilly Jane A-Frame Log Cabin Shelter (rentable at recreation.gov), an Out and Back hike of 5.3 miles and 1900+ Elevation Gain (from around 3800 FT to 5700 FT, up into the Alpine Zone at 5000 FT and above).
I was originally hoping to go beyond Tilly Jane A-Frame Log Cabin Shelter to explore the Campgrounds & Cloud Cap and hook up with Timberline Loop down to Eliot Branch River Crossing as my turnaround point, however the Snow Levels were too high to go beyond the Tilly Jane A-Frame Log Cabin Shelter as of 6/25/2022.
The Snow Levels vary year to year of course, but I would recommend waiting a little farther into Summer to do this hike if you want to add some additional Alpine exploration to the core hike.
There is an amazing American Legion Amphitheater near Tilly Jane A-Frame Log Cabin Shelter as well just past the Shelter worth checking out.
It was clear blue sky with a Low of 53 and High of 73, and this was hiked just after sunrise and there were NO Mosquitoes.
As far as road conditions, it's highway and well paved roads until the parking lot, so it was a very easy and safe driving route.
In my opinion, the road most definitely DOES NOT require 4-Wheel Drive, however do watch for road conditions, particularly snow/ice depending on the time of year.