YES! Your kids can hang out at the library - its a wonderful library and people are nice and helpful. The downtown section is easy to walk about. The Goodwill Park is in the center of town and it is a great place for kids of all ages. There are also 4 casual restaurants in the downtown section that welcome kids - they can get snacks, sandwiches and ice cream.
During school starts and endings there are crossing guards at key places to offer more safety for kids to cross the street - therefore making it possible for the kids to walk to town after school.
Many of the shopkeepers will get to know your kids - which makes our town feel so comfortable.
I have lived in Holliston for 18 years - I love the town - my family has enjoyed this town. I raised 2 sons here and they have turned out more than OK :)
So come on by for a visit - I will personally give you a tour - it would be my pleasure!
Good luck and please let me know if I can be of help.
I do not live in Holliston but I have several friends (with pre-teen children) that do. What I hear from them is that the schools are fabulous...one of the children has a learning disability and receives excellent services!
I find it funny that you inquire about "hanging out" at the Library. All of a sudden this is what the middle schoolers want to do...even here in Northborough. How ironic that they WANT to go to the Library....there could be worse things I suppose. The students in Holliston are no exception. There is a Library in the downtown area. While I don't know how long it will permitted by the Library Staff, the kids do indeed meet there and hang out...unsupervised.
I hope this gives you some perspective and helps you make the decision about your new home purchase. If you'd like to talk with a parent with similar aged children to yours I can arrange that!