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Seeing as America wasn't colonized until the 1600s none of them would have an actual Medieval feel. Although maybe St. Augustine, Florida and some of the really old towns in New Mexico would have things that come close. (More Renaissance though, I'd think) Some of the Indian Pueblo towns, like Acoma, were founded in like the twelfth century but probably don't fit what you're meaning.
Boston is a fairly old city, for the US, that has an "early music festival." Early music often includes Medieval. It also looks like it has some Gothic and Romanesque revival buildings.
As Gothic and Romanesque Revival are based in Medieval architecture I tried to look for what towns are most dominated by that style, but I'm not having much luck right now. I know some parts of the South romanticized the Medieval era and I think Natchez, Mississippi has a great concentration of pre-Civil War buildings. Back to the rest of the country I think San Francisco has something of a Medieval folk scene.
So, you're basically just looking for imitation half-timbered architecture? There are a handful of towns with sizeable proportions of it - I know of some in New York state, but the names aren't coming to me. Perhaps someone else will know.
The closest thing to *real* Medieval architecture in the US is known as First Period architecture, which is mostly found in coastal New England. It is reminiscent of the late Medieval English style, originating in the 1400s. Most American First Period architecture dates from the 1600s. The most intact clusters of existing First Period architecture can be found in towns like Salem, Ipswich, and Saugus, MA.
St. Joseph, Minnesota - Home to the college of St. Benedict. Motto of the town apparently is "Tomorrow with Tradition." Although Benedictines are actually fairly modern and liberal.
Subiaco, Arkansas - German monks important to its history. (Also Benedictine, but I'll list it as I know it. It's not really that Medieval, but they do maintain some tradition)
Vina, California - Apparently best known for a Trappist monastery.
Then there's Newport, Rhode Island and Santa Fe, New Mexico as they have some pretty old structures. However I think it's likely they're not what you mean.
There are a lot of (mock) Tudor villages in Westchester county, NY and in north Jersey, too.
Elementary School in Mount Vernon, NY
Pondfield Road, Bronxville, NY
Not Tudor, but this outlook near New Paltz, NY has a Medievalesque look
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