Rating the Towns 2009: Cities 25,000-50,000
Westport and Glastonbury seem to be pretty much written in stone as Nos. 1 and 2 in this population group. Both towns boast terrific schools, a low crime rate, a relatively good local economy (even though it might not be quite where it once was a couple of years ago) and plenty of things to do.
The jockeying continues a pretty good distance below those two, although in very small increments. Newtown and Cheshire each moved up a notch, for example, and New Milford dropped from No. 3 to No. 5. In fact, no new town entered the Top 10 since the 2006 results.
Sometimes the rankings don't quite do justice to the disparity between two positions. In house prices, for instance, Westport's 2009 median of $970,000 is larger than the combined median selling prices of Glastonbury, Cheshire and New Milford. Even among the other Fairfield County towns in this group (Newtown at $500,000 and Trumbull at $370,000), Westport is in a world of its own.
Elsewhere, young families might look to Southington and Newington, where the cost of a house isn't too high and the schools are pretty good. The bottom two finishers, East Haven and East Hartford, suffer big-city problems in their schools and on their streets, but each also offers affordable water views, the former of the Connecticut River and the latter of Long Island Sound.