I am well-aware that Williams is an incredible place to go to school, definitely among the best (if not the best) undergraduate experiences in the nation. Both its tangible assets (alumni network, endowment etc.) and intangible assets (community, undergrad attention etc.) are truly impressive.
So, two questions:
Why isn't Williams College a more recognized name nationwide? Is it because it is not truly on par with the Ivies?
Does this lack of relative prestige bother Williams students and alumni?
Could be several reasons: smaller student body than the Ivies means somewhat fewer alumni. Location is a bit off the beaten path. Sports teams are not nationally known. No graduate program.
As for #2, I’m not an alum, although I know a couple. I suspect they recognize that it is very prestigious to potential employers, grad schools, etc. If one were to base prestige on name recognition, Ohio State, Alabama, UConn or FSU would be among the most prestigious schools in the country!
Williams is consistently at or near the top of the list of liberal arts colleges in the country. Isn't that prestigious enough? It's significantly smaller than the Ivy League schools and does not have graduate programs so of course it is less well known than Harvard, Yale and Princeton. Harvard is an internationally recognized "brand" in the way that a small liberal arts school is not but if you are looking for a small liberal arts college, then Williams would be a much better fit than Harvard.
I didn't go to Williams but I have several friends who did and, as you noted, it has a very loyal alumni network both in terms of giving to the school and hiring/mentoring other Williams alums. I don't think any of them think twice about an alleged lack of prestige relative to HYP. On the other hand, as noted above, those schools are internationally recognized "brand names" (like Oxford and Cambridge) and might open doors that a smaller, less well known school would not.
Why isn't Williams College a more recognized name nationwide? Is it because it is not truly on par with the Ivies?
Your mom’s friends, your neighbors, the guy who works at the local record store might not know Williams, but when you apply for jobs, the people responsible for hiring certainly will.
Does this lack of relative prestige bother Williams students and alumni?
Not in the least. I find it a positive. Under the radar but highly prestigious among those in the know. It’s a good place to be.
Williams, as well as other NESCAC and similar schools, ideally attract discerning, but not prestige-seeking, students. Although discernment and prestige bear a relationship to each other, possessing the former seems substantive, while pursuing the latter seems superficial. And in no event would I pursue the latter at the expense of the former.
Regarding your second question, if (at least the overwhelming majority) of alums and students were primarily focused on attending a school with widespread name recognition and which would impress the man on the street, they wouldn’t have applied to Williams in the first place. Which is why, personally, I’d rather spend four years among that group of people than with a similarly-qualified group who would be bothered by the lack of prestige / name-recognition. In short: if you are the sort of person who this would really bother, Williams is probably not a great fit for you. Beyond being respected enough to get into the grad school or attain the job of your choice (it is), why should it matter, anyway?