Starting running again

I just got back from my best run of the summer- a 9 mile jog around Brookline with some former teammates. I'm finally starting to remember how to run. The first week back running is always horrible for me; my legs ache, my breathing is heavy, and I have to battle to not get passed by middle-aged hobby runners. It's amazing to me that in a month I'll be running 3 times as much as I did last week, and I'll mostly likely feel better doing it.
On another note, like Hutch, I'm also hopping on a train this summer- Train 100 by Cross. However, it's not the 100 Pounds by Cross Train (I'm shooting for 85- only 7 pretzels and 3 peanut butter crackers per day), it's the 100 Pushups in a Row by the First Day of Practice Train. Can I do it?
p.s. I know it probably doesn't help with running