Thanks much, and sorry for my delayed response! Glad it was helpful.
Bedford: Lovely town. Done a lot in last decade to make center quite nice--new facades on stores, etc.; in past, at times, looked a little shabbier. Wish I knew more about the schools--I've never heard anyone rave about them they way folks do about Lexington's for example (though have also heard about them being pressure cookers), but haven't heard complaints either. Obvious advantage over Carlisle is quick access to shops (TJ Maxx, Starbucks, Whole Foods, etc.) and to 95.
Tried to look up rankings (and of course these things have to be taken with large salt grain), and this is the latest I could find:
Best Schools in Boston: Our exclusive ranking of the top cities, towns
I do think Carlisle is pretty special. Was thinking back on my childhood and it really was as close to Norman Rockwell-esque as one can get: bike riding with neighborhood children, square dancing at the annual Strawberry Festival (put on by
the Unitarian church for everyone), shucking corn at the 4th of July parade. For that kind of small-town feel, it's just hard to beat. The education, as well--not even sure it can be measured; there's just a feeling in the town that there is nothing more important. I think this stems in part from the literary/intellectual history of the area (specifically of Concord), which seems to infuse the culture and continues to attract exceptional and inspired teachers. I've heard many people say--even through and after college--that their best teachers remain those from Carlisle and CCHS. Here's the obituary of just one of those teachers:
Wilson Flight. There are so many others I could go on about.
One other side note: I do think it was a little challenging to go to a regional high school from elementary--we were sort of the little fish (about 40 kids in my grade went on to CCHS from Carlisle) in a bigger pond (about 200 kids in the grade total). But the bonds between those 40 are pretty incredible--some 20-plus years later, so many of us are still close. Almost like family. And it was also exciting to go off to the "big city" (ha) around 13, when you're ready for a change.
A few other things to mention: band at both Carlisle and Concord is a huge thing--seems most of kids were involved in music in some capacity, and band wins all sorts of awards, travels abroad, etc. Was nice because it wasn't like there was a strong sense that being involved in music was "nerdy" since so many kids did it. Sports are good but not overemphasized (can go too far, though--when I was there they didn't build a track because wanted to tip money more toward academics--thankfully, they've since built one). High school itself is being torn down this spring, by the way--you may know this--new one currently under construction.
But again, there are downsides to Carlisle--with the two-acre lots, can be a bit isolating, to both kids and parents, and the drives to stores can be onerous. Being on Concord line, though, would really make all the difference in this regard. If I were to move there, that is where I would live.