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WilcoLovesYou t1_istd1tc wrote

I love Pittsfield and I'll vouch for it being significantly safer than its reputation, but I've also heard the school system isn't the best.

Any of south county should be fine (Lenox and south), or if you want to be in central Berkshire county I've heard good things about Waconah regional for a high school. Waconah is the regional high school for the towns of Becket, Cummington, Dalton, Hinsdale, Peru, Washington, and Windsor.

Any of those towns are perfectly safe, and out of them I'd probably recommend Dalton. It's next to Pittsfield, so you have plenty of amenities (supermarkets, big box stores, restaurants, culture, etc...) but it's also a little more suburban/rural. You'd also have the benefit of being right in the center of the county, so you'd be 35 minutes to Great Barrington and 35 minutes to North Adams, and there's plenty to do in both of those directions.

The Berkshires are great, and going from what my friends with kids say (I live here, but my wife and I don't have kids), it's a great place to raise a family.

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Sufficient-Voice-210 t1_isu36rv wrote

I would add a Lanesborough to the list of safe but close also Greylock Regional Schools are really good as well

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JaKr8 t1_isukg69 wrote

If you can afford it, Lenox has great schools, a central location -10 min to pike, 15 to Great Barrington, 5 to Lee, and 10-15 to Pittsfield.

I don't think you'll find too many really bad areas in the Berkshires.

Your biggest issue will be proximity to schools.

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Sufficient-Voice-210 t1_isul6vu wrote

The most ”run down” areas are North Adams and Pittsfield but they are no where near as bad as some places

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