If writing social or ethical commentary is your strength, then it’s probably fine … even wise … to send a couple samples of your work. Just be sure to check college Web sites carefully to see if there are specific instructions on how or where to send unsolicited materials. (Note, however, that sometimes these instructions are pertinent to only arts supplements or to slides or CD’s, so you may have to wing it when deciding what to do with your own submissions.)
Limiting your extra essays to two is a good idea. If you’re undecided about which pieces to send and are choosing among many, seek out advice from someone whose opinion you trust … perhaps a history or English teacher, a club advisor, or even a Telluride mentor. (And the fact that you were admitted to—and attended—Telluride should work in your favor, too.)
In some cases you may find that application instructions stipulate that admission folks want to see ONLY the materials that they’ve specifically requested. This doesn’t crop up often, but do take the time to hunt down these instructions, as much of a nuisance as it may be, and then heed them.
If you think that any of your writing would be of particular interest to a Classics or Linguistics professor at one of your target colleges (i.e., your commentary intersects with the professor’s research or course offerings), you can also try sending your essays directly to him or her. Don’t be surprised if you get a polite but not necessarily encouraging response … or even no response at all. But, occasionally, a prof may be excited enough by a prospective student’s ideas to put in a good work at the admission office. While this isn’t quite as rare as winning the lottery, it’s not something you ought to count on. Still, it could be worth a shot. Good luck!