Yesterday morning I awoke to 26 degrees. We have had a few hard frosts now and it's typically in the 30's at night, but I think this was our first sub-30 morning.
Over a year ago I posted on some concerns I had over riding into the winter. Like many things, preparation makes all the difference. I have been using my powerful lights in the morning, and I have been able to dress appropriately as the temp has dropped, so as of yet I have had no problem whatsoever matching my set up to the weather (you may recall that I include "darkness" as bad weather because you have to prepare for it).
The most obvious change is the unpretentious Raleigh single speed. It's not as interesting as my Rawland but it's stout, has big, big tires, fenders and lights, and it's kind of fun to motor along on. When it turns icy, I'll change out the Big Apples for some studded tires, but I intend to either wait as long as I can or try to avoid the studs and go with big contact area this winter.
The other changes are less noticeable but probably more important. I am totally sold on wool cycling hats. We picked up a wonderful Grovecraft wool cycling hat last Spring for Molly. She never took to it though, and I ended up appropriating this. It's become my favorite hat - soft merino wool made from recycled (or rather re-used) sweaters with ear flaps for extra dork-credibility. Otherwise nothing out of the ordinary - wool base layers, wool socks, gloves and some Sporthill tights.
I think I have a pretty good chance of riding most of the way through winter this year. We'll see how I am feeling about that in January, however.