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Both Wilbraham and Longmeadow have excellent schools. Many professionals who work in Springfield, Holyoke, and Hartford, CT live in both towns. Both are very safe to live in, and are all-around good places to raise families.
The main difference is atmosphere. Both Longmeadow and Wilbraham are expensive compared to Springfield, but Longmeadow is more expensive. The people that I know who live in Longmeadow also complain about their draconian town ordinances. Such as: if your garage faces the street, you aren't allowed to leave it open all day, as it is unsightly; you aren't allowed to hang your laundry out to dry; stuff like that. However, as far as sports goes, Longmeadow has an excellent football team and is very competitive.
Wilbraham is more like a sleepy farm town, but with well-to-do people. It does very well academically, and is the home to the prestigious Wilbraham-Monson Academy, which has a beautiful campus in the middle of the town. Also, Wilbraham has been ranked as one of the best small towns to live in in the US.
The general idea is that Longmeadow is very nice, but is seen as being filled with "money" people (like CEOs of big companies). Wilbraham, while being upper-class, is seen as being more down-to-earth. Both are great places for families. So I'd suggest visiting each if you could, to see which vibe you prefer.
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