I ended up completing 22 miles and love my new bike. That said, I need a few adjustments, which I'm sure I'll make shortly. In the meantime, William asked via Facebook how I managed to not freeze to death on this ride. Here are a few pieces of gear I've snagged to help extend the cycling season.
Next, wool socks. Yes, there are cycling-specific wool socks. My mom bought me wool socks for Christmas and they are more than sufficient.
Moving down, sports glasses are great for winter activities. They don't fog up and allow you to cover more of your face.
Full-fingered gloves are also great. You need them to keep your hands warm and want them to be tight so you can still shift effectively. My favorite pair have leather fingertips, which make it easier to use the gears.
The black socks over my cycling shoes are booties. They make a huge difference in keeping your toes toasty.
Finally, look for longer cycling pants. I bought these capris at the Pearl Izumi outlet, but if that's not in your budget or interest, wear regular shorts under some running tights or other well-fitting athletic pant. You want to ensure it's tight so that it doesn't get caught in the gears.
Any other gear essentials for cold-weather cycling?