A former artists' colony, it's now a haven for some of the nation's most affluent people. But as far as employers go, the town isn't swimming in large corporations. So many residents avoid the tangled Connecticut traffic by working from home instead - all the amenities, none of the wicked commute to New York.
After work, locals enjoy the city's beaches and the nationally recognized Westport Country Playhouse, which hosts everything from musical revues to classic theater.
NEXT: State College, PA
Last updated July 16 2008: 1:27 PM ET