I recently visited Bowdoin and Middlebury with my daughter, and I thought Middlebury was going to be very preppy, and Bowdoin could possibly be her first choice. The day we toured Middlebury it was 18 degrees and windy, no joking, it was too cold for anyone to look preppy, she loved Middlebury. Our tour guide at Bowdoin was nervous, the student and administration staff member at the information session were preppy, but I thought nice and thoughtful young men. After the information session we asked a Bowdoin employee a question and we were taken back how unfriendly she was, to the point my daughter decided it was just time to leave, and I don’t think she is even considering applying there. Because it was February vacation they had the information session at a different location and that employee was not from admissions, but non the less represented the school poorly. The impression we got was, we gave you a tour, and information session, you are now bothering us, it is time for you to get in your car and leave, so we did. The one experience my daughter and I both noticed was when the tour guide was telling the group how Bowdoin is a heads up campus, and everyone says hi to each other, all the while class had just been dismissed and 25 students were walking behind her at that very moment, not one said hi to her or each other. From what you describe in your question, and from our experience I would NOT apply to Bowdoin early without visiting.