Getting back to Nick's original question, I caddied primarily at two different courses off and on through college.
The first was outside Chicago at The Glen Club in Glenview, IL. The Glen Club is a high end public Fazio course (all in green fees at the time from ~$175-$200) which also had ~100 "Corporate" Members. At the time, 2003-2007, there was obviously a lot of corporate golf played by guys with big expense accounts, and these types of players liked the luxury of caddies for their customers. Thanks to the economic times, I made anywhere from $120 - $200 for a variety of loops. I had a regular double bag loop that paid $120, I had two regular weekend loops which a foursome in carts that liked to gamble big, showed up 5 min before their time, and paid for two forecaddies to stand on either side of every fairway for $150. The rounds at The Glen were almost always slow, on average maybe 4.75 hours and many times 5+ hours, and because of timing and slow rounds it was rare to get more than one loop a day. However, the course operated with a "call ahead" system where if you either had a regular loop, or were requested, or a better caddie the caddiemaster would call you the night before and say "You're signed up for the 8:00am XYZ loop, get here by 7:00am" which was really nice because you didn't have to sometimes waste 6 hours just
waiting for a loop like at many other clubs. Plus, you were allowed to play the golf course for free every day after the last tee time (around 2-3pm)...which was a great perk. 95% of the caddies at The Glen were College age and under with varying degrees of skill.
The second place I caddied was at The Country Club of Brookline, which was 4 miles down the road from my school in Boston. I was a student first when out at school, but I would usually loop Friday's, Saturday's, and Sunday's with the occasional Wednesday afternoon loop when the days were long enough. The only times caddies were mandatory was weekends before noon, but even during other times I would guess 60% of rounds were with a caddie. The pay wasn't as good as in Chicago, but loops were a flat rate of $100 as a honor caddie, but during tournaments we were given $150+. I rode my bike from my apartment to the Club at 5:30am to be one of the first caddies there to get priority, and I usually got out by 8:00 or 9:00am, but the time before my first loop was usually spent either reading the paper or doing homework...so it wasn't too bad. The membership really knew how to take caddies, and other than one glaring exception the members were really great people. Most of the other caddies were either in school of some sort (high school, college, grad school) but there were a fair amount of life long caddies there...some being really interesting characters, some a bit sketchy. The club also let caddies play on Monday (which I schedules my classes around Senior year, thank you very much
) and Thursday mornings on the Primrose if you wanted to, but if it was really slow around the club and the caddiemaster was in a good mood they would let you sneak over to the Primrose to play a few holes after saying "just be back by 9am for a loop." Overall that was a great experience, as I was able to pay for my living expenses in college by looping part-time (which according to one GCA member is apparently a despicable idea) all the while spending time on a world class golf course studying it's bumps and rolls.
While not the same hub of caddie activity as Chicago, the Twin Cities have a fair amount of clubs with caddie programs. One of the reasons I joined the club I did up here was that they have an active caddie program. There aren't any hard rules as to times when caddies are mandatory, but it's expected that you take one when they're available, especially on weekend mornings. I'm fine with that as to be honest, they aren't that expensive (~$25-30/bag for a "B" caddie, ~$40 for an "honor") which apparently keeps the caddie corps young. I can't imagine there are many, if at all, experienced loopers there, but I'm not as high maintenance as many other GCAers
and have no problem with supporting the surrounding neighborhood kids.
While caddie programs aren't as prevalent as they once were, they are still available in many places, and many people still like to take them. There are many positives to caddie programs, and I would encourage others to support them at their clubs, when they are guests at other people's clubs, and through the WGA's Evan's Scholars program.