As promised, I stopped by Wesleyan earlier today to pursue your question about visiting on a Friday. There were the obligatory “Depending on the weather . . .” comments. This is, after all New England. 
Otherwise, I get mixed reviews about visiting on a Friday after speaking with 5 different students - 3 in the Admissions office and 2 others in a random Wesleyan off campus cafe. some said “it would be great” while others said “not so much”. Here’s the advice I got to maximize a Friday visit to see students out and about, knowing that at any given time lots of students are in class or in their dorm rooms:
- Attend the afternoon tour/info session, which is scheduled for 1:00, rather than the morning if you want to see students.
- Arrive early. The cafeteria is in Usdan University Center across the street from Stewart Reid House, where the Admissions Office is located. From noon on, students should be arriving for lunch. In fact, it is permissible for you to get lunch there before your tour, which would be a good opportunity to see students. Just stop in to the Admissions Office first to get a parking permit to display on your car.
- Stay late and stroll around campus after your tour & info session, which should end about 3:30. Students getting out of class at 4:00 should be milling about and making plans for the weekend. Popular gathering spots are outside Olin Library and outside Judd Hall at the end of
College Row.
One student strongly recommended visiting Main Street, which is a few blocks from campus because it is such a strong feature of the Wesleyan neighborhood and because it is where Wesleyan students spend some of their time. He suggested Cantina Cafe Ristorante next to the Italian Society of Middletown, on Court Street off Main as having great Italian food. There must be 20+ different restaurants on or just off Main St, serving a dozen or more different cuisines. Eat up!