Actually I do really like Southern Village, but it offers a pretty limited set of amenities within the community itself. I do like how easy it is to get to downtown Chapel Hill/Carrboro from there, and these offer a respectable number of cultural options. But if we stay here I probably will be working either in Raleigh, Hillsboro, or Greensboro – in other words, 30 to 60 miles away. UNC and Duke don’t offer the kinds of jobs I’m looking for (lots of teaching).
Let me recommend Burlington, VT, as a potential city that could give you the best (or at least the betters) of both worlds.
Very solid public school systems, a walkable city, depending on where you live, a number of colleges and universities in town and immediately outside of town, and generally a safe place to live, no matter what street you’re on.
It’s “urban” enough to provide a large number of artistic/cultural diversions, yet still small enough to have a very local feel (this may be a plus or a minus, depending on your own preferences).
You might laugh at this suggestion, but you might even want to look at Marshall University in Huntington, West Virginia. I went there for college, and unless it’s changed immensely, Huntington may have a good balance of the things you’re looking for. It’s a very charming smaller town, but the university provides a TON of culture and activities. It’s quite possible to live downtown in a residential area, and walk to the shops downtown. You’d even be able to let your son play outside while living there.
I’m not sure about public transportation - I know it exists, but I’m not sure about the safety factor. I expect it would be fairly safe with the university there.
(I loved it there - I would move back to Huntington in a heartbeat, and I’m a big city kind of gal, for the most part.)
E.
I live just east of Hillsborough, and I’m only 10-15 miles away from either Durham or Chapel Hill (depending on where I go), not 30. There is limited bus service (not free, though) from Hillsborough to Chapel Hill, plus other options like park-n-ride and ride sharing, so you could still live in Chapel Hill and commute to Hillsborough for work without using a car every day if you chose to do so. I’ve done both the park-n-ride and ride sharing and while they take a bit more planning, it’s quite doable. I also expect more transportation options to open when the Durham Tech satellite campus is finished in Hillsborough.
There are also regional transit authority buses that go to some places and Raleigh and you could use park-n-ride to get to those too.
Sorry, I meant Burlington (Elon College), not Hillsborough. I’m a NC newbie.
May I suggest Pittsburgh? It’s commonly considered a small “big city” and a good place for raising a family. Certain in-town neighborhoods fit your bill for vibrant, walkable, liveable communities with fairly low crime rates. There are several universities and hospital systems. Most of the neighborhoods that come to mind are the ones surrounding the universities (once you get away from the student housing areas). Housing costs are favorable compared to many other larger cities. The quality of the city schools varies by neighborhood.
The biggest drawback I can think of is a slightly undeveloped public transport system (but good enough to get around the city - more of a problem for commuters who don’t want to drive in from the 'burbs) and it doesn’t have the best reputation for biking (mostly due to topography).
I appreciate what you’re looking for, but I don’t know that those qualities exist in any particular city as a whole - we lived in Madison for 8 years, and although I was an avid neighborhood walker I never saw kids out playing, having adventures of their own. Stephen King’s childhood summers (i.e., The Body) seem to be a thing of the past.
However, what you CAN find, in many (if not most) cities, are neighborhoods, community centers and churches where parents enjoy one another’s company and the kids roam somewhat freely. You could look for a city with an outstanding park district, for example.
We’re new to town, and just last week I met someone who also moved here from Chicago. He came here 8 years ago and missed certain amenities, in particular an arts organization (which I, too, had loved). So what did he do? He started one here, patterned after it. And it’s flourishing.
Re: the “green” citizen thing, the quandry you describe is, I think, the exact reason why some people roll their eyes at certain environmental idealism - not everyone CAN live within walking distance of their needs. But is that your only option? Is it better to join a community where a green lifestyle is already established and working, or put some effort into “greening-up” a community that could be doing better?
Hey yeah, let me chime in for Ann Arbor, MI. It kind of has the best of both worlds. I’m typing this from the University of Michigan campus right now, in fact. You will have an excellent academic community, a groovy night life, beautiful parks including a botanical garden, and a good public transportation system to get you from A to B to C (in the rare cases you can’t walk.) Additionally, Ann Arbor is very safe.
I must warn you, though: You will pay up the ass for housing. You will be safe and smart and ecologically friendly, but it will cost you.
Olives!
I know this isn’t exactly what you want to hear, OP, but a good compromise might be trading off from one to the other.
What you’re describing most people go through, right? When you’re young and single you want to live where the action is. You are walking distance to the local cafe or bar and live among interesting places and people. However, when a family is in the picture you need to think about them first so you move out to the burbs where there is less culture and things to do, but it’s better for raising children.
Boston is a really neat city, but I would never want to raise a kid there, as an example.
One thing to consider: Don’t fall into the trap of trying to buy the house that you’re going to live in forever. Chances are you won’t. Most people move every 5-7 years. You probably will too, for whatever reason. If your kid is still litte, enjoy it in the city for as long as you can now. Then move to the suburbs to raise him in a safe, clean environment. You probably still have plenty of time after the kids are grown to move back into a loft in a neat urban area with lots of culture when you’re an empty nester.
The consensus is that the schools in some of the immediate (and transit-accessible) suburbs such as Newton and Brookline are top-notch. I’m very happy with the public schools where I am, in an adjoining town, though this school system would not be top-of-mind when people list off the good school systems. And yes, the area is expensive, though if your wife is a doctor, you’ll get by.
Personally, I think your idea of settling someplace quasi-permanently, so your kid is not disrupted by constant moves, is the right approach, if a little countercultural.
By the way, I know Burlington, VT a little, and it’s also a nice place, though I don’t know how the public transit is – just buses, I think, and I don’t know how extensive the service is.
Hey, how about Montreal?
Elon University is in … yep … Elon! 
Burlington’s next door.
And you can still have ride-sharing options, even from there. I think once you’ve been in the Triangle area awhile and learn more about the area you’ll see there are ways to have most, if not all, of what you want right here.
If you move someplace with mild winters, you can commute on a nice little Vespa-type scooter. I would love to use one here instead of my car, but it’s kind of impractical when you have to park it for seven months of the year. 
I think of my childhood as pretty ideal in the ways you’re describing. There were lots of kids on the block and we’d play stickball/stoopball in the street. (Car!) It was a couple blocks to a large park (payground when we were little, then frisbee/baseball practice/hanging out when we were older). I walked to my elementary school and my middle school. I babysat for the younger neighborhood kids.
I grew up in Brooklyn. We moved there in 1981. I was 6. There were crackhouses on our block – huge expanses of burned out rowhouses (like in The Wire, only not so bad). And a biker bar on the corner (actually, the bikers kept the crackheads in check). A lot of storefronts were empty or marginal.
Around 1986, the crackhouses were renovated and sold as co-ops. The neighborhood is now one of the most desireable in Brooklyn. A house similar to my parents sold for $2.5 million last week!!!
I wouldn’t exchange my childhood for any money. There is a value in being exposed to an urban environment. I grew up street-smart and independent. I went to London on my own at 16 and had no problems getting around and taking care of myself (I started riding the subway alone at 12, that would be 1987 for anyone keeping count, just a couple years after Bernie Goetz waxed a couple would-be muggers on the subway). (note: I am a very small female person)
Brooklyn, says I. Best place in the world to raise a kid.