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In the Orlando area where I live there is Mt. Dora. There is a lot of victorian era homes and sidewalk shops. It feels like a very small town that is quaint and quirky. More old people than quirky young people, I must admit. There are a lot of small town culture there!
I grew up in Pittsburgh...live in CO now...I love Pittsburgh...so many cultures there!...Try the strip district...southside...shadyside....lots of great food!...I live in Nederland Co now...that's about as quirky as you can get and I love it!!
I was born and raised in Asheville, NC. Besides the yuppies pouring in at an alarming rate, it's definitely a unique town.
Also...
-Minot, ND (or North Dakota in general) has a nice quirky feel.
-Tehachapi, CA area has a nice (and still unknown) mix of artists/musicians etc..Like Sante Fe, NM minus the insanely high cost of living.
Honorable mention:
Duluth, MN
Bangor, ME
Chadron, NE
Butte, MT
Bend, OR
Flagstaff, AZ
Dare County, NC (until it succumbs to the Myrtle beach virus)
Eureka, CA
I think Dubuque should get an honorable mention for sure. If only by comparison with the rest of Iowa. For 2 examples, it has an inclined plane and a Roman Catholic archbishop.
Just about any city built in the late 19th/earl 20th century will have some quirky architecture. Newer cities might be more cookie cutter. You could look into St. Louis. It has fabulous brick homes, at an affordable price, and not much cookie cutter in the city.
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