Cheshire, a little stuck up. Have a good friend that lives there. Expensive town, very yuppie/preppie, have met a lot of people from there who think their s&*t doesn't stink. A lot of anti-gun liberals living there, including the new congresswoman for the 5th district. She's one of those "why do you need more than 1 bullet in a gun?" type of people.
Southington, blue collar town, kind of densely populated, lots of shopping available.
Woodbury, nice small town, friendly people. You have to go to Southbury or Watertown for any decent shopping.
Southbury, low taxes - Heritage Village has about 6000+ retired folks living there that pay property tax but don't have kids in the schools. Region 15 school system is outstanding....although Cheshire and Region 14 (Woodbury) are too. Southbury has all the shopping centers adjacent to 84 but you can drive 5 minutes and be in the country.
If you do settle in the area and you're looking for a good gun club - http://www.nwcsa.org
About 45 minutes from Southbury/Woodbury/Cheshire, probably about the same from Southington too.