One admissions office I heard speak at a roundtable night cautioned not to interview too early. So, what do you think the “optimal” time is? We won’t have to travel more than 3 hours and his school is okay with him missing to go on interviews. He did attend open houses last year at all of the schools he’s interested in, so I don’t feel he needs to do that again.
Just checked DS school calendar and he has Dec 13th off. Too close to winter break? Finals?
We had to travel across country, so we interviewed in the end of September and end of November, so time missed was in two different quarters for DSs school. I think being more local would make that scheduling easier, though. With DD, we will try to postpone until October and January, but her school does trimesters…I’m really not sure if timing matters too much. An outstanding candidate is an outstanding candidate.
We scheduled our interviews between mid October to mid November. I don’t think there is anything wrong with waiting until December as long as you book the date far in advance. You should ask if your visit will coincide with exams or other major events.
More important than timing is your sons preparation for the interview. He should do some mock interviews with you or another adult and be able to talk about his interests, why he wants to go to BS, and what types of classes he enjoys and why.
I don’t know that it really matters except to get them on the calendar. All kids and families are busy, and even if the visits are “excused” for school purposes, you still need to schedule them when it works best for your family, school, and outside activities. I am sure there are arguments to be made for early/late/anything in between, but I wouldn’t worry about it too much and just do what you think works best for your family and your son. I would, however, consider how tightly or widely you space them (to the extent you are flexible). I know that some kids do several interviews over the course of a few days. My son found the visits and interviews exhausting, so we spaced them out over the course of about 4 weeks (4 interviews + 2 shadow days), and even that was pretty tiring for him.
I definitely agree with what CTMom21,buuzn03 and dramakid2 wrote, and my only piece of advice would be don’t schedule interviews during Parent Week/Weekend. It will be super busy, and most schoosl don’t have the week open anyways. You can probably find the academic calendar on their website. We have a 24 hour flight to get to the States, and found out I won’t be able to interview at Hotchkiss due to the parent week problem. Oops! At least we’ve got Skype.
My kids interviewed in the fall - mostly Oct/Nov. One interview might have been the beginning of December (on a day off from school - they were given several days off in the fall for secondary school visits). It was better for them to visit/interview earlier so they finalize their list and focus on applications.
Good point about parents’ weekends, which often start before the weekend. Also, depending on where you are going, weather can be a factor and create some uncertainty once you get into December (and sometimes before). DS interviewed at one MA school in late October 2 days after an early snow/ice storm. It didn’t affect us but would have been a problem for someone traveling from farther away if it was on the snowy day!
Most of our interviews were via Skype after applications were turned in. It worked out for us because by then, our daughter knew all the schools well and knew her own strengths from having written her essays.
I have to concur with this, as others have as well. The optimal time you what works for your family. Just get them on the calendar ASAP since they fill up. FWIW, I interviewed over the summer, although not all schools offer summer interviews. But again, that was what worked into our schedule.
But ya know…the plural of anecdote is not data! 
We did interviews between fall break and a week before apps were due…onsite AO, Skype AO, local alumni…doubt timing made any difference…but no idea in the end.
Just interview well! And perhaps more importantly, don’t interview poorly. I personally believe interviews serve as more of a weeding out, than a weeding in. If you’re solid on paper, have good LORs and fill a need for the school (particularly a hook), you really just don’t want to show up in flip-flops and not be able to carry on a conversation.
I think they use interviews to weed out the most obnoxious families and kids… though that is hard since everyone is on their best behavior 
Sadly, not always true. I’ve given a few tours to some families with less-than-stellar behavior, and was surprised to find junior on campus in September.
And a new library named after Grandpa?