After having run a single loop around the Driftless Horse Trail before, I finally decided to go for a double loop run. The day started in the morning going with a clockwise loop first, and then went counter-clockwise for the second to get different views and climbs. Weather was fortunately cooler with low humidity for an August day in Wisconsin. The original goal was to complete the run somewhere around 5-6 hours, and had fortunately went better than expected.
I went solo for this run and carried a hydration pack for fuel and water while running the loops, and stopped at the car for some refueling in between loops, thereby making the run self-supported. The trail was in good condition, with some overgrown areas but runnable throughout. Just had to be careful to dodge the horse piles. The route is great for some alone time and social distancing, since I did not see a single other person or horse for the entirety of the run.
I was unable to get photos put up on here, but feel free to check the Strava link for some views from the trail and what the loop start areas look like.