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thoermann - what type of lifestyle are you looking for? country bumpkin? in-town? public or private school? Commute locally or out to Albany, etc./?
Having grown up in Great Barrington and going back often to visit family, here's my observations about the Berkshires:
- Figure out the lifestyle and then find the town. If you want hip in-town living, then Great Barrington would be a good pick. Less cool but more affordable and up-and-coming is Lee. Gentleman farmer: check out Egremont. Upscale in-town classic cultural hotspot: Stockbridge or Lenox.
- Families travel to events. There's not always going to be stuff going on "in town" and folks always go a town (or three) over to attend an event. Likewise there may be one great facility, such as the new community center in GB, that will draw from all around and thus prevent the need to be duplicated everywhere.
- Schools may be town-based such as Lenox or regional (such as Berkshire Hills, which serves GB, Stockbridge, West Stockbridge). So, there may not be a need to pick one town over another for schools. However, you kiddos may be on l-o-n-g bus ride. There is also school choice, in which towns/districts participate and allow kids to attend. I believe the towns exchange the $ and parents just need to get their kid to/from a bus stop or drive to school).
- The Rt 7 corridor has the larger towns that may have more going on and to the east and west it becomes the *real* boonies pretty quick. Also - what's your tolerance of NY weekenders w/ $$$ descending on your town, creating traffic, having stores that really cater to them, etc?
Good luck!
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