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Western Massachusetts to Aspen, CO

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Need to deliver a canoe to Aspen, CO, by or before Wednesday, 7/19/17.
Need to be back in the Amherst, MA, area by Friday night, 7/21/17.

Proposing a departure date of Sunday, 716/17.
Hoping to deliver the craft Tuesday, 7/18/17, if possible, just to be safe.

IF necessary, I could leave Massachusetts Saturday evening, 7/15/17.

I have free accommodations in Manhattan, KS, both ways.

Questions:

Since I've never driven quite this far before and not in a westerly direction, do I have enough time to make my delivery deadline without cutting it too close?

Also, KS aside, I'd like to sleep in my car or using airbnb's. In other words, I want to spend little to nothing on accommodations. Any suggestions?

Same goes for food, CHEAP, but not junky.

And if there's anything else you can think of I'm all ears!

Thank you!!

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