Like you, I was a transfer student (we’re talking twenty years ago), though I was transferring from a community college (I don’t know your situation). I was an A student and figured that I had options. I had a sense of wanderlust, wanting to get far away from IL. But I wanted to go to a good college. Obviously, I wasn’t going to transfer to Harvard! So I looked for “hidden gem” schools, excellent LACs (I knew that this was the perfect environment for me) that would provide a solid education. I dreamed of going to Willamette in the PNW, Austin C. and Southwestern U. in TX, and schools in the NE like Clark or Wheaton (the one in MA, not IL). Note: I ended up attending a LAC in IL. 
Like you, I too read about “concerns” regarding Worcester, a blue-collar city, not a classic college town. Now that I’m older, I’m sure that Worcester is just fine, and there are plenty on this site who went to school in MA or who live in MA and can give you more precise information. I guess I’m saying that I was like you: someone looking at schools in MA but not knowing much about the area.
BTW, if you do get into Holy Cross and it’s affordable, that might be your ideal choice. Terrific school. Rigorous academics. But it also has the traditional social scene. Even though HC is quite progressive for a Catholic school, I’d guess that its students are much more centered than the left-leaning Clarkies.
EDIT: There’s a thread here (it shouldn’t be too buried, as it was active a day or two ago) where someone is deciding between HC and Brandeis, two schools that you also applied to. I realize that Brandeis is not an option for you because it is too expensive, and you haven’t heard from HC yet, but if you’re interested, you might take a peek at the thread.