I just ran my fourth race last week - the Cleveland Turkey Trot 5 mile. It was an adventure - there were over 6,000 runners. I might not be in any of pictures, though - I had my jacket tied around my waist and it was obscuring my bib number. My official time is 55:06, not too shabby! Below is a picture of some of the many participants before the start of the race.
I just finished reading a Jeff Galloway book, and I find that the running books help keep me motivated, too. Daily Mile is also great for motivation!
I'm worried about the winter, but will keep running even if it's on the treadmill. I do plan to run outside whenever possible. Next possible race is December 3rd - haven't decided on that one yet. Otherwise, my next big goal is the half marathon in NYC in April 2012!