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I'm planning a 3 week trip traveling back and forth across east coast states Indiana, Ohio, Virginia, Tennessee, Kentucky, North Carolina, Georgia to look at sites and possibly look for a new small town near a a larger city to move to and partially-homestead and grow apple, pears and other deciduous fruit trees / grapes. I will be taking this trip starting from Saint Louis Missouri by car from the 17th of June to about 7th of July. I already planned to stop for the last day of the Bill Monore Bluegrass Festival in Bloomington Indiana and at Hocking Hills State Park in Ohio . I like guitars, Blue Grass / Older Country Music , Hiking, BBQ, Ice Cream, Pizza, Fried Chicken and the US Civil War. What are some towns I should check out to live in and / or things I must / should see or do? I'm a single work from home software engineer, who is agnostic and a libertarian .
From what your interests are, I'd recommend you don't go further than the Appalachians/Blue Ridge. Pass on the coast. There are beautiful towns and a lot of things to see, but I think you'll like the mountain areas better. In Virginia absolutely visit the Shenandoah Valley. There's tons of Civil War history, beautiful views, cute towns, great hiking, and bluegrass. In particular, visit Harpers Ferry (which is in WV but it's right on the border. Worth the visit), New Market (battlefield and Civil War museum), and Lexington (Robert E. Lee and his horse are buried there). Patsy Cline was from Winchester but there isn't much to see about her there.
Check out Bardstown, Kentucky. I stopped there on my last road trip (July 2021) and was very impressed. It's a quaint, historic town in a very scenic area. It's also the self-styled "Bourbon Capital of the World".
You've also got the Chickamauga and Kennesaw Mountain Civil War battlefield sites, both in Georgia.
Both Abraham Lincoln and Jefferson Davis were born in Kentucky, and their birthplaces are both preserved as historic sites.
There is a lot of good hiking in Southern Indiana. A lot of people think of Indiana as being totally flat, not realizing that most of Southern Indiana is very hilly. No, it isn't the Rockies or anything, but places like Hoosier National Forest and Monroe Morgan State Forest are great places to go for a hike. I'm not really into anything else you listed, but I do like taking weekend trips to Southern Indiana. If you're into wine, Bloomington has a couple of excellent wineries. Bloomington also recently got a shoutout here --> Secret US wine regions you need to know about
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