Are there bike trails near enough where you could do a multi day ride? I rode through Chicago using the Lakeshore Trail and connected to some some nice trails east of Chicago. Seems like there were a lot of trails in Chicago.
I highly recommend the Natchez Trace Parkway for multi day riding but it involves travel and you’d need support.
Are you looking to stay on paved roads or could you do gravel/unpaved roads, too?
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