Using paper and electronic together.
Google maps will show the quickest route while trying to keep you on Interstate at the same time. You only get to go exactly where you want by planning it out for yourself. The maps will show you all the other roads available and what attractions are along them. Take a look and see what appeals to you and make notes and then you can go back on-line and do some research, whether it be a small town, a City, or State or National park. Once you have some places you want to visit you can start to see how to join those dots up, you can check mileage via Google maps, but time estimates are way to optimistic. If you average a drive along the highways as covering 55miles in one hour you will get a good idea of how far you can get, but that's not allowing for major sightseeing stops, just the basics for food, fuel and rest. Once you have got those 'Waypoints' you can even drop and drag the blue route line on Google to see how much mileage it might add. You can do this multiple times for each day, you just need to start breaking things down into smaller portions and then piece it all together. When you get to this point and you have specific questions, we can help to 'fine tune' your options.
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Also, when would be the best time to drive/sightseeing each day? I'm thinking driving in dusk, and then visiting during day light
There is no 'best' time to drive, other than it being light for the main part so you can enjoy the ride. The rest will depend on how your plan comes together. For example you might spend the night in town and your main focus for the day is 5 hours away, so you set off after breakfast. Another day yo may wake in the place you want to explore and will then set off in the afternoon /evening depending on how far your next destination is. It will come together as soon as you have started to break it down.