At this time, the two were corresponding regularly about Pyle’s illustrations for Wilson’s “Colonies and Nation” which appeared in Harper’s Monthly Magazine throughout 1901.
On December 1, 1900, Wilson wrote to Pyle:
I find (have only just now found for certain) that the date fixed for my lecture before the New Century Club in Wilmington is December sixth, next Thursday. I am to stay at Mr. Job Jackson’s [at 1101 Washington Street]. If you are to be at home the next morning, will you not let me know at what time I may call on you? A lecture rather does me up; but the next morning I will be fit to enjoy myself again.Pyle replied on December 3, 1900:
Of course I shall be most delighted to see you, say at my studio the day after you lecture here in Wilmington. I am only sorry that we are not to have the pleasure of entertaining you. I shall probably see you the night of the lecture.And then a few month's later, on March 6, 1901, Pyle asked: “When do you come to Wilmington again? Do not forget that the next time you are to stay with me.” Wilson replied the next day: “Thank you very much for saying what you do about my staying with you the next time I come to Wilmington. The idea is most attractive. May the thing some day happen!”
So it’s still up in the air if Woodrow Wilson visited Howard Pyle on December 7, 1900, and I’m inclined to think Wilson never wound up being Pyle’s house guest once their collaboration was over. But if ever I obtain corroborating evidence, I’ll let you know.