Where's all the talk?
Anyways, having grown up in western Mass, I've always said rural/small town New England would fit the vibe of a Wes Anderson film (He managed to make me think "Rushmore" was filmed in the Northeast, and in my opinion the setting for "Fantastic Mr. Fox" looks more like New England than old England). So I'm wicked glad to hear this. And I think the 1960's is a good move- detractors claim his films are unnaturally quirky and nostalgic, so why not set it in a quirky time that people get nostalgic about?
Any thoughts on soundtrack? Bowie's really early stuff could work for the period. Also, early BeeGees songs - "The First of May" would be perfect for the young love story; and maybe "Massachusetts" (if they set it here, that is- there's 5 other states to choose from, and knowing Anderson, he will likely not specify).
Arlo Guthrie had a lot of great tunes. I think "Ring Around-the-Rosy Rag" might fit nicely, and although he is of southern origin, he has ties to rural New England from the 60's- go watch "Alice's Restaurant" (1969) - great film set mostly in the Berkshires (Norman Rockwell-land).
Speaking on Norman Rockwell, I would not be surprised if his art is an influence to Anderson here. Rockwell did covers for "Boy's Life"- the boy scout magazine, and many of his famous paintings are set in New England, some featuring scouts, as in the below 1969 painting, "Beyond the Easel".