I can’t vouch through personal experience with the jobs and internship situation at Wesleyan, but, the infrastructure certainly seems to be in place for finding them:
http://www.wesleyan.edu/careercenter/students/jobs-and-internships/index.html
As for going to a “lower par” school in order to find jobs in perhaps a bigger city, you have to take into account that with more jobs there will almost certainly be more competition for them. And at Wesleyan, you’re not just limited to Middletown; the entire state of Connecticut is within reach by car - if, it comes to that.