We are heading into the best riding weather of the year here. I love October! I can enjoy the fall colors and ride in cooler (but not yet cold) temperatures. I do have to shift the time of my rides earlier in the day to get back before dark.
November is fine too with some cool-weather gear. I won't ride with snow or ice on the ground or if it's truly cold out where you don't start to warm up after about 10 minutes of pedaling.
I've never been a runner. This winter, I'm planning to shift my activities indoors and (gasp!) go to the gym. Or sit on my couch and knit and get fat.