I went 9.5 miles today, almost an hour worth. Ride went great until I found the hill. Up hill about 40 degrees (is there a way to check that on Strava?) and in a turn. I lost my momentum and mis-shifted so I pulled off the road for a second to regroup myself. Took a drink of water, spun into the gear I wanted and got up there. I hit a small rock going fast down a hill and sounded like the tire was punctured but it kept air and I didn't see any damage when I got home.
I was actually quite tired this time. I think I will need to stay at this distance or try this route a few times before attempting more. Of course it was much hotter today than it has been too. Below is a picture I took on my way. Went through some farm areas, was a beautiful ride in that particular segment of the ride. I even passed some fellow cyclists going the opposite direction of me.