Longfellow's study, which is at the right of the house, and which to-day fronts the long conservatory occupying the entire side of the house, was used by Washington as his dining-room. Above it was his private office, where councils of war were held. It was a very convenient room for this purpose, being off from the main house, quiet and retired. When Longfellow first purchased the house, he also used this room for a study, afterwards converting it into a chamber.

It is said that Washington never permitted his affairs to destroy his sense of humor. During the time of his occupancy here, an elderly woman was brought before General Putnam. She was believed to be a spy, although she stoutly denied it. It is said that the general, familiarly known as "Put," regarded the case of sufficient importance to be brought to the attention of his commander and insisted that she come with him to headquarters. She was an obstinate woman, and having no fear of capture, resented his treatment, absolutely refusing to enter the gate to the grounds. In vain was she reasoned with until at last, in desperation, the valiant general slung her on his back and brought her up to the house. As Washington witnessed his most courageous officer entering his house in this manner, he could not refrain from laughter, which only incensed the woman all the more.

During conferences at headquarters, great care had to be taken lest they be surprised by the British. While one of these conferences was being held, word was sent out that the British were on their way. Without a moment's delay each officer hurried for his necessary adjuncts to meet the emergency. In the midst of the confusion, however, General Greene lost his head and could be heard above the din, calling loudly: "My wig, my wig; where is my wig?" His demand was so emphatic that the attention of the little group was instantly seized. General Lee was the first to regain his composure and with ready wit called out in an equally loud voice: "Behind the looking-glass, General." Greene, passing the mirror, found to his consternation that the wig was on his head. Overjoyed that he was not to go into battle wigless, he joined in the general laugh that followed. The report of the British approach proved false, however, and the officers returned to their consultation.

After the estate had been confiscated, it was purchased by one Nathaniel Tracy, an intimate of Washington, whose principal home was in Newburyport, Massachusetts. Tracy was a very wealthy merchant, indeed one of the most brilliant financiers in the country, and his spectacular ventures had given him a prominent name in local history. Tracy was a large landowner, having estates practically all over the country, and while he owned the Vassall house, he rarely lived there, using it simply as a place where he could spend week-ends if he so desired.

Andrew Craigie was the next prominent owner of the house, purchasing it on January 1, 1793. At that time the grounds had been enlarged until they comprised one hundred and fifty acres, a part of which is now used for the Harvard Observatory. This Craigie was an "apothecary-general" or, as he would be known now, a commissary, for the Continental army. He was a most eccentric man but clever enough to acquire a large estate. This house appealed to him, both from the fact that it had been Washington's headquarters and from its own beauty both of exterior and interior. He married a Miss Shaw of Nantucket, who had been in love with a young sailor of limited means. The wealth of Craigie dazzled her, and while she never forgot her early lover, treasuring his love letters until just before her death, she made a charming mistress for the mansion.

Craigie, like other wealthy men of his time, was pretentious and spent money lavishly. While it is believed that he built the service department on the western wing of the house, yet this is not definitely known. During his occupancy, the large, square, eastern room was enlarged and adorned with many columns to afford more space for his frequent entertainments. Prominent merchants of Boston and many noted people accepted his hospitality. An amusing instance is told of a visit of Talleyrand, who conversed entirely in French with Mrs. Craigie, the host not understanding a word that was spoken. It is currently reported that the Duke of Kent, Queen Victoria's father, who for a long time was stationed at Halifax, paid a visit here; impressed with the honor, Craigie afterwards purchased the coach and horses the duke had used in Boston.

Craigie built the bridge from Boston to East Cambridge which bears his name and engaged in many investments. He speculated once too often, however, and lost nearly all of his money. He died soon after, but his widow remained in the same house, yet under such reduced circumstances that she was obliged to let rooms to college students. Two of these were Edward Everett and Jared Sparks, who afterwards brought their brides here.

Later on, when Henry Wadsworth Longfellow left Bowdoin College to take a position as professor in Harvard University, and desired extensive apartments, he appealed to her. She at first refused him, having tired of the care of students and not wishing to let rooms any longer. He was an attractive and agreeable young man, and when Mrs. Craigie learned that he was a professor, she invited him to visit the different rooms, telling him of Washington's connection with the house, but informing him that he could not have the use of any of the apartments. At length, however, after a long controversy, she agreed to let him take the southeast chamber, to which was afterwards added the west front chamber for his dining-room.

At that time the back part of the house was given over to a farmer and his wife, the latter caring for Longfellow's rooms and supplying his meals. During a part of the time that Longfellow had rooms here, Worcester, who wrote the dictionary, was another occupant. To this house came Cornelius G. Felton, Charles Sumner, and many others to visit Longfellow, who in 1842 entertained Charles Dickens here.

In 1843 Longfellow bought the house of Mrs. Craigie. He was the last occupant, and every room in the house is connected with him. In one of the upper chambers Hyperion was written, as were many other poems, including The Courtship of Miles Standish and Hiawatha.