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GO FOR IT!!! Two years ago my wife and I took my 1967 Fairlane down Route 66 leaving Wisconsin and going as far as Tucumcari, New Mexico then Northeast back home. We only had two weeks and wished we'd had two months!!! The car ran fine and we met so many wonderful people along the way it was just outstanding!!! This Country of ours is overflowing with amazing things to see and great people to meet.
Stay on the 2 lane roads as much as you can. Do lots of research to check out sights along your route. Your Southern route sounds like you can do lots of Route 66. Your Northern route runs close to U.S. 30 which stays near I80 and is as historic as 66. Michael Wallace, who wrote a great book about Route 66, said it best when he wrote "Life begins when you leave the Interstate".
I carried a small emergency kit made up of a small tool box, electrical and bailing wire, extra points, cap and rotor, extra fan belt, a gallon of pe-mixed antifreeze, nylon cable ties and an electric fuel pump with a rubber line on each end, hose clamps and long wires with alligator clips that I can hook on the car battery. Should the stock fuel pump fail in the middle of nowhere, I can hook up the electric pump and it will get me to the next town.
I'm sorry I'm so wordy but GOSH I envy you. I'm planning on taking my PV444 on about an 800 mile trip in June as a shakedown for longer runs in the future. My "Bucket List" is to head toward your location to see Dearborn Village, the Civil War battle grounds, the Smithsonian and points East.
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