It just depends on your lifestyle. I would suggest you do a few Sundays of open houses, go to some tag sales, go to the library of each town and the town hall of each town. I would also suggest you go buy something down at Peter's in Weston and then go to Trader Joes and Fresh Market or Whole Foods in Westport. Time how far it is to your pediatrician is to your target areas. I would also try to park in downtown Westport and walk around down there. Go to the beach, to Sherwood Island in Westport and to Bisceglie Park and Devi's Den on Pent Road in Weston and see if you like the facilities there. Take a tour of the schools. I can help you. I am a native of Westport and grew up when Weston used Staples as a High School so Weston also feels like my town.