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For small and quirky try Matlatcha, Florida just northwest of Fort Myers. It's an art and fishing community located on the way to a larger island in the Gulf of Mexico. Main street is lined with brightly colored, funky and very creative art galleries, bars and a few waterside casual outdoor restaurants. The whole area there along main street that you drive through and walk on going from shop to shop, from one side to the other--water to water is about 200-300 feet wide. Where it gets wider are all sorts of trailers, many decorated oddly, and hand built cottages that the artists, musicians and fishermen live in. Very cool place!
Provincetown MA is incredibly quirky and charming. It's gay/lesbian index has it at 2 times the national average (according to Moderator cut: link removed, linking to competitors sites is not allowed). It's got stunning New England architecture, wonderful beaches (it's surrounded by water on 3 side), excellent restaurants and bars, a cool observation tower/ monument from which you can see all of Cape Cod and on a clear day, the Boston Skyline. Whales swim right off shore. It's got a strange blend of cultures... Portuguese fisherman, yuppie tourists (summer months), a strong GLBT community, and a stong presence of nature lovers.
The thing with so-called quirky towns is they're usually so-called "art communities" *yawn* made up by hipsters trying too hard to act all quirky in order to rebel against their suburban middle-class upbringing, which through their plastic quirkiness manage to ba as homogeneous as any cookie-cutter subdivision.
Being quirky is like being cool. If you try it to hard then you certainly ain't it.
Eventually, hipsters and aging frumpy aging gays a charming city make not.
Probably the closest you would get to a genuinely quirky city is New Orleans, but that can work both ways, and in any case NOLA is also going through a preocess of "hipsterization".
Savannah, GA is quirky in a New Orleans sort of way.
I found Eureka, CA to be rather quirky.
Lots of quirky little towns in Maine...once you get past the touristy places.
For small and quirky try Matlatcha, Florida just northwest of Fort Myers. It's an art and fishing community located on the way to a larger island in the Gulf of Mexico. Main street is lined with brightly colored, funky and very creative art galleries, bars and a few waterside casual outdoor restaurants. The whole area there along main street that you drive through and walk on going from shop to shop, from one side to the other--water to water is about 200-300 feet wide. Where it gets wider are all sorts of trailers, many decorated oddly, and hand built cottages that the artists, musicians and fishermen live in. Very cool place!
I drove through this last week for the first time. Definitely quirky...feeling of the keys.
Love that quirky charm - no cookie cutter allowed. Let it all hang out. Places like New Orleans and Savannah come to mind. Where to find the genuine, honest characters and real sense of place?
I think Savannah is overrated...Charleston up the coast is more interesting
further up, Wilmington for a smaller town
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