Wellesley and Needham have good schools, which is the initial draw for families. Both towns also have neighborhoods so that you get to know your neighbors and kids can play with the other kids on the street. While schools in other towns such as Dover, Sherborn and Weston are also very good, there are fewer traditional neighborhoods because in these towns, minimum lot sizes are generally much larger.
In both Needham and Wellesley, the school districts for the grammar schools are mapped out geographically so that your children become friends with the other children in the immediate area. There are great parks in both towns, particularly in Wellesley, for smaller children. Warren Park on Washington St. in Wellesley is a draw for people from all surrounding towns for its new play structures and its shade in the summer and the sledding hill in the winter. There are family friendly activities sponsored by both towns year round including parades, concerts, street fairs, open houses at fire stations and more. The towns are generally very safe with serious crime being very infrequent (details are readily available from local police departments). Amenities such as quality child care facilities (for working parents) are available as are organized recreational programs (the Y in Needham has great programs and the town of Wellesley offers programs for adults and kids year round ranging from T-Ball to cooking to yoga).
From a practical perspective, both towns offer local shopping areas and several restaurants that are kid friendly, and they are also easy access to larger malls and commercial areas as well (Route 9 in Natick/Framingham and Highland Ave. in Needham are both accessible).
Both towns also offer easy access to Route 128, the Mass Pike and thus to Boston and other areas so that working parents can get back to town for appointments or other engagements without too much difficulty.
Again, I hope that some of the foregoing is helpful. Please let me know if there is any other information in particular that you would like to know. Andrea
I combining your homes search with family friendly communities, I am biased towards Holliston. Even though the downside is that it is off-the-beaten-path, that is also one of its strengths. This town is the same community I remember growing up in.
Now if you need to work in Boston, and you have the ability to afford a Wellesley, Needham or Weston, they are great options. But if you have a smaller budget, Holliston offers a great community for half the money.
Holliston schools win great recognition, score well on tests, are reasonable sizes, and have unique programs like a French Immersion program. There are about 5 parades that my family attended last year, as well as a model train show, an antique show, a senior class auction, Friday night football games, and neighborhood block parties.
All religions seem to coexist in town, with several strong churches/synogogues of different faiths. Downtown has barely enough stores for a walking tour, but it also keeps the traffic down to a minimum.
This community is small enough to be fitting the phrase "it takes a village" and to have it actually happen.