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Originally Posted by nouveau.mere
Middletown is not the type of downtown we are looking for. There are more restaurants than anything and most of them aren't as family-friendly as we would like. We have an under 1 year old. Thanks for any thoughts you have though.
Just difficult to switch from the Boston area.
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I understand why you like West Hartford, but you should be prepared to commute 1 hour each way. You can take Route 9 to Route 17 to Route 77. If you don't hit any traffic, maybe it will be under an hour, who knows. For a better commute, consider the Westville and East Rock neighborhoods in New Haven. They are nice, safe neighborhoods, with pretty quick access to downtown. If you really want immedate access to "downtown," you could live in one of the nice apartment buildings on the New Haven Green (eg, CentrePointe). Downtown New Haven is closest to Boston (though still very different), with a reasonable commute to Guilford.
If you haven't seen it, check out Branford, too. The Branford Green retail district is not very different from Madison or Guilford (maybe it's a little busier), but I'm not totally sure what you want, and you might like it.