The Chestnut Hill area (off of West Mountain Road) is a real nice area. I haven't lived in Simsbury since I was younger (10-12 years ago), but that was the area where most kids were. Also the area between Old Meadow plain and Latimer Lane is a nice area too. From what I remember those were two areas with a lot of Kids playing outside. I know there are more, generally if you stay around the elementry schools you should be ok.