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I should also have mentioned Jacksonville in southern Oregon (not to be confused with the much larger Florida city). It is a historic small village surrounded by scenic countryside that a good friend visited with me in 2007. You can basically walk the entire town and the population can't be more than 5,000, but there are a surprising number of good restaurants there and even a little nightlife. On the downside, stores seemed to close a little early, but it was very pleasant and the people were friendly.
It is an easy twenty minute drive to Ashland with its historic Shakespeare Festival and only about fifteen minutes from Medford. Crater Lake National Park is about 80 miles away.
Poughkeepsie, NY. I made a few visits over the summer and walked on the Walk Over the Hudson bridge, which is amazing. The general area is very quaint, relaxed and has a down to earth atmosphere that I like. Natural beauty is very nice, too. And some amazing turn of the century architecture.
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...and the surrounding area is one of the most beautiful places in the country
Hyde Park is nice. The Culinary Institute kinda interesting, too. I toured it years ago; you could have lunch, too, not sure how it is now. The FDR home there, too.
My car broke down in Ukiah, California, and I had to stay overnight and all the next day. It was a really nice city, the more so for being in California.
Glad to hear you had a good experience! That is a beautiful area in the redwood forests. About 30 miles south of Ukiah, equally obscure Cloverdale is a nice town, too. Further south of there is the Wine Country with more well know towns like Santa Rosa, Napa, Sonoma and Healdsburg (those four are definitely not obscure).
Lynchburg, Virginia
Savannah, Georgia
Marathon, Florida (in the Keys)
I know I live in Georgia and all, but I really don't think Savannah is obscure at all--especially since it tends to rank very highly in many tourist magazine lists.
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