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Thoughts on initial stages of planning East Coast trip

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Very initial steps of planning a voyage to the East Coast. I am just looking for basic advise and opinions at this point. We are 2, 20 something friends who just returned from DC and had a blast. Next thought is a possible trip to Boston (as we are history buffs). Ideally we would like to fly into Boston (from Chicago) either on Saturday or Sunday. Sight see Sunday, Monday, Tuesday, and possibly Wednesday.

After Boston is where I could use the advise. I should preface by saying that I am one of those people who want to visit every state (even if it is literally to put my feet in the state and exit 5 minutes later just to say I was there, I know I will catch flack for that being a travel forum and all but that's the way it goes). We would like to do a loop around the neighboring states. Possibly starting south and hitting Rhone Island and Connecticut on Thursday. Vermont, New Hampshire, Maine on Friday/Saturday (I've already got New York checked off my list). I know Google Maps says most of the drives are roughly 1-2 hours.

I suppose my question is this. Even though I am fine with "just stepping into the state" or "driving though," is there enough to see along the drive, the coast etc to make the trip worthwhile? I found a rent-a-car for roughly $80/day plus no mileage costs (we'd have to pay gas obviously). Are there enough hotels along this route we would be able to just "stop for the night?" We are looking into the first week of October again. Any and all suggestions are very welcomed. Like I said, I know this is not enough information but I just want to make sure its worthwhile before jumping into vacation mode. I can get obsessive about it as I know I am not alone in that respect..... Thanks in advance.

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