Ok, here's my [insert old "2 pennies" emoticon here]:
I agree with Jela (YEE-la), that the general premise of the song is completely from Allison's POV; here are the lyrics as copied from the website:
I'll respond to you in letters
Sorry so slow, sorry so few
In a nutshell, I'm much better
So far the complaints I hear are few
So how have you been? Have you been to the races? Did you take my mother --
Is your sister in braces? I wish I could've been there to see you through
Hey, are all those things you told me once still true?
Do you remember that time
It was cold in the park
You were running a race, I was there on a lark
Who would've thought that New York could be such a small town
Margaret is tired,
let's let her get some sleep
Bored with these letters,
let her count her sheep
So goodbye love, goodbye love...
The first "races" seems to be something that Ellis could have taken her mother to, so whether that's a race he ran, or foot races they could watch together, or horse races they could watch together... but it doesn't seem like it could be a political race.
The second "race" he was obviously running, in a park, in NYC, in the late fall/winter/early spring time, and she just happened to run into him there. What an astounding coincidence! Wow, who would have thought that NYC could be such a small town?
So... yeah, I guess I'm saying that the first one could be either, as she is asking if he took her mother to the races, but the second he was obviously running. Yep. My 2 cents.