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Whether the small towns of the Northeast or the villages of Sicily, all of your photos have in common walkable, mixed use places. Wal-Marts and other big boxes stores don't have that. Suburban sprawl neighborhoods don't have that (or have it in a very limited capacity). I think that's a big part of what people are responding to.

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I think this is completely correct and now I am going to go crazy figuring out is actually going on. Some of it may be that the sheer scale of big box stores means that there is a lot less visual interest; having a bunch of tiny shops makes for a more human-scale variety.

Also, having different brands matters--part of the sameness is literally the chain store issue.

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Wal Mart is a place you have to go, not enjoy going to. 20 years ago, teenagers loved the mall - but they were anchored not just by the kids who wanted to be there, but by the adults who needed to go there. The age of big-box-budget stores and delivery services for everything killed malls which had previously killed main streets. Toy stores? Book stores? Hobby stores? Comic stores? Arcades? I'm sure you can find some, but it's so much easier to get all of that delivered to you, and it's much harder to get out of your neighborhood and go anywhere because of massive arterials. Main streets bounced back for bars and restaurants, and to some extent they are more convenient to go to when you want to go out than going to the mall. The best malls are the ones that connect to main streets.

So I don't think it's sameness that bothers us. I think it's a sense of inviting-ness. People don't stop downtown for a bite - they go out of their way to go there. People dont stop into Costco, they make it a trip. But main streets are something you can both sorta stop by in your neighborhood, and are a place you go out of your way to go to. That's my hypothesis for small town looks - they're inviting in a way that no other retail is, even if they mostly just give you bars and restaurants.

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I still recommend you visit Farmvillle,VA. We also fell in love with Athens,OH but I think you would like FarmVille more

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Didn't they make a game about that place?

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