@CaliMex GG’s school was supposed to be Choate. Was it called Westerburg or was that in Heathers? Anyway, the town was supposed to be Wallingford as well, based on the location between the grandparents in Hartford and the nasty kid at Yale. A character mentioned going to a record store on the Berlin Turnpike in passing. Now the small-town silliness may have been based on Washington or Kent or any of those nowheresville NW CT towns, as Stars Hollow was nothing like Wallingford. But SH wasn’t like Washington, either. And GG Hartford wasn’t like Hartford. Yale wasn’t…
@CaliMex -Not sure… I should probably get with it and finally watch Gilmore Girls… I hear it’s great.
The first Friday the 13th movie was filmed on Lake Waramaug … I always thought about Jason for some reason when I was there for rowing… no idea why. Probably because that first Friday the 13th totally freaked me out. Ruined camp and camping for me like Jaws completely ruined swimming in the ocean. Thanks, Hollywood.
Gunnery has a great Crew Program that launches and trains on Waramaug and they host Founder’s Day which is a fantastic regatta … definitely add that to the Gunnery plus column!!
Also- for parents touring schools in that area, I highly recommend Whitehorse Tavern for lunch/ dinner or Marty’s for coffee and a snack or just a delicious casual luncheon. Great atmosphere and food at both places! The Pantry ( in Washington Depot near Marty’s ) is also quite good for lunch but I believe they’re closed on Monday. 
Most small schools don’t have large endowments. The schools on the OPs list are all well-known for rejecting qualified candidates because of the lack of FA money. Groton has a large endowment, St. Andrew’s, too, based on endowment per student, as that’s the only measure that counts, but the FA money is with the larger, more famous schools. Hotchkiss has all the money they need for FA. Cheshire Academy does not. CA may award the lottery to one kid or something, but many, many kids will be shut out completely. Hotchkiss can award the lottery to anyone they feel like. Yes, smaller schools do offer FA, but the generous schools are those dozen at the top with the cash. They are also the most competitive. That’s racing.
I am sitting on my hands…
@CaliMex Yes, the small-town inanity may have been based on Washington Depot–though I heartily believe that was a clumsy bit of retconning after the show became popular because no one who at ever been to Choate or Hartford or Yale or Connecticut before had anything to do with that show; it was pure LA smeared on a map of New England.
Chilton. Alex Chilton, not Paul Westerberg. Meta meta. I’m sure ASP enjoyed her first trip to CT long after the show became popular. If she’d ever been to Connecticut, she would have put the parents in Cos Cob, the Inn on Rockwood Lake and that idiot kid at Greenwich Academy. Would have worked kinda okay for the Yale thing, too. But tv’s not real; thank the gods.
Note: when I say rejecting qualified candidates because of a lack of available FA, I’m including an ‘acceptance’ but $0 FA or a ‘FA waitlist’ in that category as well. Someone got in and got the money, but not you. You were rejected, no matter what the letter says.
For FA families, the small schools are often niche admits, thus the legit great hockey player gets into a certain hockey-focused school with all the required FA while other anodyne smart kids get nothin’. Find the school that’s your perfect fit and you just might win that lottery.
Also, keep in mind that demonstrated interest is important. If your kid is a fine athlete and instead of a 77% test, they get a 98%, well, a Canterbury or a Gunnery might decide that your kid is going to get into Choate or Kent, so they take him out of consideration. If you truly want the smaller schools, you need to prove to them that you don’t want Choate or Kent or Andover or Groton, and you really will attend their school if admitted with the requisite FA. That’s not always easy. Honesty helps.
For (significant) FA families, everything is 50 times more difficult. You need to be honest with yourselves and be ruthless in your pursuit of your goal. Don’t apply to any school that you would not attend without hesitation if admitted with the needed FA. Make sure your top school knows they are your top school. If you get into just one school with the needed cash, you have achieved a glorious victory and are allowed no more than 23 hours of complaining about all the schools you didn’t get into.
“For (significant) FA families, everything is 50 times more difficult. You need to be honest with yourselves and be ruthless in your pursuit of your goal. Don’t apply to any school that you would not attend without hesitation if admitted with the needed FA”…absolutely true!! This is something I wish we’d known when we were going through — the schools make it seem like asking for FA is no big deal— when in reality it is quite the opposite!!! we were fortunate that our situation worked out like it did. I would strongly suggest that if FA is needed, the net needs to be much wider and do NOT apply to a school you really aren’t that interested in. There are many many schools out there that your child would thrive in and LOVE…so make sure those are the ones that are receiving your application. Also, the 50 times more difficult is not much of an exaggeration, if any, either.
It is the cold, hard truth, but I wish someone had slapped us with it before we were deep in the application process-- it would have made things easier to understand and cope with when it was all said and done.
Agree about St. Mark’s and they have a healthy endowment as well. I have many relatives who have attended. Since they admit many day students, the competition for admission as a boarder is even higher than their already small size would suggest. Westminster is similar in that way.
In an interesting twist… http://www.courant.com/news/connecticut/hc-kent-second-gilmore-girls-fan-fest-20170719-story.html
MODERATOR’S NOTE:
I don’t recall the OP indicating that a reenacting the Gilmore Girls experience is a priority, so please move on.
Apologies to the Original Poster for hijacking the thread. I hope you don’t mind the detour 
A friends son was very happy with the hockey program at St Marks (and the rest of the school). He played in college too (D3 I think).
We are very happy with St Marks! And to address a prior comment- they limit day students to 13 per grade, so it is not overwhelmingly day students.
@CaliMex No worries, I took some time and stuck my head in the sand once the difficulty of this began to settle in.
I now completely understand the need to cast a wider but it does seem like with each additional school it will be even harder to convince any of them they’re our priority. We will look into the other suggestions though.
@cgb_prep we applied to 11 schools. It was not at all hard to see which ones rose to the top…and DS ended up at the perfect school for him. Wide nets are important, but the schools that are good fits will be obvious. And in the end, it is still likely you won’t be faced with a decision…it will be made for you. We realized this can actually be a huge blessing!
According to the website, SMS is 25% day. Same as Westminster. Certainly not overwhelming but significantly higher than the others on the OPs list and to my point above it means that the number of boarding admits is smaller than one might otherwise suspect from the size of the overall student body.
I will mention something else about the schools with a large day student population, and from your list, specifically AOF and Westminster, which are both in suburban (by CT standards) areas and draw heavily from the local neighborhoods. When you get up to a 20-25% day student level, I think the school atmosphere/culture seems to feel more like the local area and reflect its demographics. That may not be meaningful if you are from far away and aren’t familiar with different towns, but it was a factor for us and my son. For applicants from outside the area, it is probably a matter of just determining what “feels right” (in addition to all other, more objective, factors), which is hard to do without visiting. If at all possible, I think visits (while school is in session) make a big difference. The brochures and web sites all look perfect, but it’s so hard to really know without being there.
^very good points @CTMom21! To expand on that, schools that have a lower day school (K-12) will also have a very different feel than those just 9-12. And those with an affiliated JBS may also have a slightly different vibe, depending on the area/other schools around. For example, Deerfield is remote with an affiliate JBS nearby. You cannot emphasize the importance of visiting enough, and be sure to do so with the students there! That’s the best way to get a feel for the school and its community.
Hope this isn’t too much for OP but I think it’s invaluable info that I learned through trial & error with K1 which I’m hoping will serve us well should K2 decide on BS.
@Temperantia I’m not sure which website is quoting those stats—I just know that being an SMS parent—they limit day student spots to 12 per form. So, giving yield error, that’s roughly 50 out of 370 students. My DS has not noticed there being an overwhelming population of day students and knows a few kids that chose to board to increase their chance of acceptance. SMS also holds “community weekend” 1-2 times per month which requires kids to stay on campus for school bonding activities.
Not trying to be argumentative- I just want to be sure views aren’t skewed.