I went to Pomona (graduated 1988); my sister went to Williams (graduated 1989). As far as I understand they are ranked about equally academically. Two of the most difficult small private liberal arts colleges in the country.
Williams is several hours from the nearest large city, out in the woods. It snows in the winter and you can cross country ski to class. Pomona is within the Los Angeles megalopolis. Beach and mountains and desert are all day-trips.
The biggest benefit of Pomona is that it’s part of the Claremont Colleges, and you can take classes at the others if you choose. I took economics classes at CMC and computing classes at Mudd, literature classes at Scripps and a psychology class at Pitzer. Effectively it makes for a much wider variety of educational opportunities.
When I was there we used to go in to LA — I would ride my bike along Arrow Highway out to Pasadena and down to USC, and get a ride back — or to the beach, or up to the mountains or out to the deserts for camping trips. We’d socialize at the other schools. Go to Scripps dining halls, hang out around a fire pit at Mudd, play ultimate frisbee at Pitzer, argue about politics and economics at CMC.
Pomona’s number is 47, by the way.
My sister thought the benefit of Williams was the isolation and the small-school community, and the woods. I’m glad I had LA, the desert, and four other schools to roam.
None of my employers in the tech industry have ever seemed to care where I went. I do get confused with Cal Poly Pomona. But the education and the friends and connections have been valuable, and the Claremont experience — five campuses worth of interesting people — was something I’m glad I had.