Life in the White House during the Woodrow Wilson administration featured moments of great happiness and joy for the president as well as times of deep sorrow. His beloved first wife, Ellen Louise Wilson, died from Bright's disease on August 6, 1914. Her death devastated the president. Always in need of female companionship and affection, Wilson eventually recovered to court and marry Edith Bolling Galt on December 18, 1915. Age forty-three at the time of their wedding, she was a Washington widow. They did not marry in the White House, however, because the press had been filled with much malicious gossip about Wilson’s lack of respect for the memory of his first wife.

Wilson's vigorous progressive agenda and supervision of the war left him little time for recreation. Upon the recommendation of his doctors, Wilson regularly exercised by playing golf, although he thought it a silly game. He also rode horses and enjoyed cruising Chesapeake Bay aboard the presidential yacht Mayflower. Above all, he loved to go for a ride in the country in the White House Pierce Arrow limousine.

For entertainment, he liked to attend baseball games, vaudeville performances, and musical comedies and especially enjoyed, in the privacy of the White House, reading aloud from favorite English poets. When in a frivolous mood, Wilson mimicked political rivals or told so-called “darky stories” from his youth (one issue in the present-day disputes over Wilson’s racial legacy). When the whole family was at home, they often gathered around the piano to sing hymns and popular songs. His eldest daughter, Margaret, who was twenty-six in 1912, was a professional soprano, who often performed at Army camps during the war. She never married, eventually moving to India to live as a mystic. Jessie, a year younger than Margaret, and Eleanor, three years younger, were married at the White House in 1913 and 1914. Wilson was devoted to his family, once bitterly lecturing reporters at a press conference for intruding on the family's privacy when speculations about the girls' romances appeared in print.

Wilson screened the first feature film ever shown at the White House, D. W. Griffith's The Birth of a Nation. The film was based on a novel by one of Wilson's former students, Thomas Dixon, and was shown at Dixon's request. Its crude racism and argument that Reconstruction had set blacks free to prey upon defenseless whites in the postwar South did not fully reflect Wilson's opinion of the period; in a book about the history of the era, Division and Reunion, he had written that the end of slavery was a benefit of the Civil War although elsewhere he was critical of black involvement in Reconstruction. Wilson said nothing about the movie at the time of its showing, but a few days later, the White House issued a statement dissociating the president from the film's viewpoint.

Nevertheless, many years later, a film publicist attributed to Wilson a colorful comment about the film that became famous. According to the story, Wilson was supposed to have said, “It is like writing history with lightning. My only regret is that it is all so terribly true.” While Wilson never appeared to have uttered those words, his personal and political ambivalence towards the full rights of African Americans as equal citizens undoubtedly contributed to the staying power of the story.