Zach:
It ain't that cold in KY yet (I'm from East TN, although transplanted to NC now). For me, about 50 degrees is the low limit on surface temperature for me, although we've got some nuts up north who run in the snow, bless their hearts. More power to them, but that just doesn't work for me.
As it cools down, try to run in the afternoon or early evening when the sun has warmed the asphalt/concrete all day; that way, even if the air is cooler, you'll have fairly warm surface under your feet. And don't be tempted by grass or VFFs until you've got a few months of BFR under your belt. You need the flat, hard surfaces to safely transition due to several factors:
- the sole skin conditioning effect hard surfaces have when used with good form
- the painful feedback hard surfaces provide instantly when your form is poor or gets sloppy
- the smoother transition to extending your achilles tendon (as you move from wearing heel-elevated standard shoes t0 putting your foot flat on the ground, especially while running)
- danger from the uneven ground under grass as you go through several months of getting your fine motor control muscles and tissues in your feet back in shape after years of lazing around in shoes
This is the "avoid Phil's stupidity-induced stress fracture" plan, provided at no cost to you courtesy of TJ and many others here at BRS. I tried to start too fast and in VFFs. Go with 1/4 or 1/2 mile every other day BF with at least 1 rest/skin recovery day in between at first. Add a little distance every week or two as you are comfortable, listening intently along the way to the feedback your feet provide. VFFs kill that feedback and will cause you to hurt yourself. Think of them like a 4WD truck - both will take you places you might not ought to go, and from which you may not be able to get back. Both can be great tools when used properly, and indidiously dangerous when not give the proper place and attention. Fair warning from one who has gone before you, who was warned, and who didn't listen until the 10-week stress-fracture healing enforced training break.
Welcome to the crew. This is a great place with lots of great folks who will gladly share with you from their wealth of experience. Glad to have you with us!