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You'll definately be improving the school situation for your children by moving to any of these three towns. I've lived in Hopkinton and Westboro and there are pros and cons of each. I think it really depends what you're looking for.
I have a friend who lives in Hopkinton who was complaining the other day about the "townies" who want to keep the town with the same old character and not allow big chain restaurants and stores, whereas the big chains and all that traffic that goes along with it I would find dreadful. Westboro on the other hand has about every big chain restaurant or store you could want, which my friend would find convenient (although not likely when he tried to drive through the congested downtown), and I find unappealing.
All three towns have very lovely neighborhoods, good schools, tons of activities for the kids.
I don't think Westboro has done a good job with planning roads and such and Hopkinton has not done a good job of protecting open space. However, I like the small, family run businesses downtown Hopkinton. It's nice to walk in and have somebody know your name and help you find what you need.
In Hopkinton you can easily get train access (unless you're at the far end over near Upton, in which case it's kind of a hassle to get to). In Hopkinton and Westboro I liked having really easy highway access (except when we lived on the west side of Westboro it wasn't easy).
Some of my fave neighborhoods:
- Charlesview Estates in Hopkinton (nice homes that aren't cookie cutter, mature trees, tons of kids, walkable to park & school)
- Old Colony Dr & the streets off it in Westboro (I grew up there so I'm partial to the area. It's a pretty, tree lined street with a mix of home styles, a bit further from the highway but easy to get to the train. Homes don't turn over there very often.)
- Northgate in Northboro - (very cute, well kept Cape-style homes walking distance to elementary school and easy access to Rt 135/9)
Anyhow, I hope my rambling is somewhat helpful. :-)
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