In the middle of the night recently he awoke convinc'd that 'twas he who had been haunting Mason,— that like a shade with a grievance, he expected Mason, but newly arriv'd at Death, to help him with something.
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Line 28 Vulgarized:
As revelations are sometimes wont to do, one woke Cherrycoke in the middle of the night to declare itself. Perhaps living Cherrycoke was haunting newly dead Mason as opposed to the other way around as one would expect. Instead of a ghost looking for help from the living, perhaps to move completely to the other side, living Cherrycoke was looking toward the recently deceased Mason to help solve a problem.
Subtext:
What is history but looking for answers from the dead? Mason & Dixon is first and foremost fiction. But Thomas Pynchon writes a peculiar type of historical fiction which can be considered, in many ways, history through a lens of exacting historic detail as the stage setting and props for modern viewpoints and whimsically hilarious lies. Just as Cherrycoke looks to the past and his deceased friend, we look toward our own past, and history (sometimes the 18th century), for answers to questions that haunt us in the middle of the night. Mostly questions of the "why are we here" and "what does it all mean" category. Surely somebody has figured it out at some point? And might we be capable of discovering their answers?
Cherrycoke is simply acting out that feeling we've all felt, many different times in our life, best exemplified by a line from Simon and Garfunkel's "America": "I'm empty and aching and I don't know why." Come to think of it, how many words has Thomas Pynchon written across how many novels just to express that one line?
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