I suppose we can't really have a thread like this and not feature a town I have always found fucking annoying, Woodstock, NY.
Most people have heard of Woodstock, NY, even if they haven't heard of pretty much every other town on this list, due to a dirty hippie music festival held miles away in another town entirely. Because of the dirty hippie music festival, hordes of dirty hippies subsequently moved here, followed by shockingly clean hippies and then, finally, Daniel Craig.
However, what most people don't know is that before the music festival in another town, Woodstock was a picture-postcard perfect little village with a Greek Revival Old Dutch Church and a town green bedecked with posies and antique street signs.
It was the location of two of the most significant developments in American Modernist culture, the Byrdcliffe Colony of 1902 onwards...
...and the Maverick Concert series, held at the remarkable not-quite-open-air Maverick Hall.
The list of artists associated with both are too long to recite here: suffice it to say that composers, musicians, theater directors, painters, architects, fashion designers and artisans moved into the community and restored the commodious 200-year-old homes.
And occasionally built rather alarming variants thereof.
And the Woodstock Artists Association Museum became one of the most important small collections outside of any major city of early through mid-20th century American art (also housed in a 200-year old building, natch).
For this reason, the folk of Woodstock turned up their noses at the famed music festival and its dirty hippies, and "Woodstock" would be more properly named "Bethel" by anyone who was paying attention.
But the hippies came anyway and turned the town into the peace-love-harmony bedlam beloved of people who have never seen the place today.
I'd love to tell you it sucks, but I actually have numerous great childhood memories of the place - Christmas shopping with my family in great little toy stores full of electric trains and handmade puppets, my grandmother taking us to the Woodstock General Store (sadly no more) to buy penny candy, hitting the Bearsville Theater to see musical acts, watching Santa get "rescued" by the fire department from the church steeple, spending many happy hours in the Golden Notebook Bookstore (still there, praise the maker), so I must admit to soft spot in my heart (and, given the amount of time I spent later on as a teenager making out behind the movie theater, an equally hard one in my dick) for the old dump.
And - I dunno - ain't Grandpa Woodstock kind of cool?