I recall in the 80s the fist Christmas toy runs in my town were held in December, looked just like your pic. Then they figured out "If we hold it in September more people will come!"
I rode in 12 degree temp on a December day to try out my new heated vest. It failed the test. I have pretty good gear. I can ride in the 40's if the sun is out. I can't do it all day. A couple of hours and I'm an ice sculpture. It's not on my list to do anymore. In my 70's, it isn't enjoyable.
I rode mine to work one day it was low 30's in the morning but supposed to be upper 50's at quitting time. Open face helmet, no fairing or front fender and the worst gloves I could've chosen. First thing I noticed was that all the shady spots in the road were covered in frost, by the time I got out of the city and on the 60 mph back roads I became painfully aware of the glove choice. They were a mesh like outer with leather palms, by the time I got to work 30 minutes later I could hardly get my helmet off because my fingers didn't move. I hit the bathroom and ran them under cold water and it felt like a million needle pricks, they stung for another 20 minutes after that. One other guy rode in that day with his full dresser with all the shielding that lived 15 minutes out, heated grips, heated seat, heated jacket, chaps, full face helmet, said it wasn't a bad ride. Lol
Here is my last motorcycle that I converted, a Moto Guzzi LM III has 17 inch wheels, a different fork, better brakes, once in the original design and then as a Cafe racer. Greetings Harald
1989, Me on my then daily driver, xv920 rh. Man I loved that bike. I put 60000 miles on it in just over 8 years of ownership.
Here's what you've all been waiting for. My 1947ish Motoconfort Scout 50cc. The motor is 1980s and the wheels are mountain bike. In fact there's not much of the original bike left. So yeah, your Harley may be bigger, but mine's much slower. It'll go about 40mph actually. Which is plenty.