D_Malley - Honestly, I wouldn't think at this point in the season that many clubs would want to take on an extra part-time caddy. As someone who recently spent 4 years caddying full/part time at one of the top clubs in Westchester, I know our caddymaster would never bring someone in at this point in the game. Rounds are going to start decreasing as kids are back in school, the weather begins to turn, and even football starts. For the loopers who make this a full time gig, this is now their time to earn the money that will hold a lot of these guys over for the winter. The college and highschool kids are gone, except a few that will come back on weekends, but certainly not enough to be needing more help. The guys who have been working hard all season deserve all the extra loops they can get, which is why I wouldn't expect it to be easy to find a part-time looping gig at this point.
Virtually all the private clubs around metor-nyc have caddy programs, and between metro-north and the LIRR, most are easy to get to.
Westchester:
WF
Quaker
Fenway
Bonnie Briar
Wykagyl
Century
Westchester
Braeburn
Purchase