After the mansion staff party, the Roosevelts adjourned to Lafayette Square where FDR would light the community Christmas tree and speak to the nation via radio. Beginning in 1936, the Roosevelts' official Christmas duties concluded with ER's visits to the residents in one or more of the city's many alley slums. They or a local sponsoring organization such as the Council of Federated Churchwomen or the Alley Dwelling Authority would provide a lighted Christmas tree for an alley, and the residents would gather there for carol singing and gift giving. ER would speak and help distribute the gifts.

When the alley celebrations ended, ER returned to the White House where the rest of the family awaited her. They would then hang their stockings on the mantelpiece in FDR's bedroom. Early the next morning they would gather there to see what "Santa" had brought, a process that ER noted always took "a long time" because of the number of children and dogs involved. The family then had breakfast and went to church. After lunch, long distance calls to any absent family members and naps for the youngest children, the Roosevelts opened the rest of their presents around the family tree. The day ended with a gala dinner for family and close friends. (Twice during the years the Roosevelts spent in the White House, ER missed the Christmas Day celebrations. In 1936 and again in 1937, she opted to spend Christmas with an ailing child. In 1936, she spent Christmas in Boston with FDR, Jr. who was recovering from a sinus operation. The next year, 1937, she traveled to Seattle to be with the Roosevelts' daughter, Anna, who had suffered a hemorrhage).

Between Christmas and New Year's Eve, the Roosevelts hosted private social events such as parties for their grandchildren or dances for their children. In 1938, the president and first lady gave a debutante dance in the White House for ER's niece, also named Eleanor Roosevelt, preceded by dinner for "so many cousins from different sides of the family" that ER and her brother, Hall, spent the meal trying to identify the younger generation "by their resemblance to their parents." Sometimes the Roosevelt children hosted the parties as Franklin Jr. and his first wife Ethel did in 1937 and 1939. Occasionally, the Roosevelts would attend affairs outside the White House during the holiday season. In 1939 for example, ER attended the fiftieth wedding anniversary celebration of former Secretary of Commerce Daniel Roper and his wife, Lou, and in 1942, the family attended the December 26 wedding of their cousin Belle Roosevelt in nearby Fairfax, Va.

The advent of World War II in 1941 both expanded and contracted the Roosevelts' Christmas celebration. For example, better economic conditions meant ER attended fewer holiday parties for disadvantaged children. Instead she used the time to visit wounded servicemen at Walter Reed Army Hospital. Wartime conservation measures made it impossible for FDR to light the community Christmas tree (now set up on the South Lawn of the White House), but the audience for the ceremony and his message grew to include members of the armed services overseas who heard the ceremony via shortwave radio. The Roosevelts also scaled back their private entertaining, and the number of family members who gathered at the White House (or at Hyde Park where the Roosevelts spent Christmases of 1943 and 1944) shrank as the their four sons and one son-in-law joined the military. However, FDR and ER continued their annual custom of meeting with the president's executive office staff on Christmas Eve, and the party for the mansion staff, which now included all the military guards at the White House, went on as before although tinsel for the White House Christmas tree became increasingly difficult to obtain due to wartime rationing. In 1944, ER admitted to feeling "rather discouraged about how the tree would look" but she took heart when a girl scout troop gave her two boxes of ornaments made with peanuts, straws, cotton paper doilies and red ribbon four days before Christmas. Once on the tree, she found the ornaments looked "very charming and as Christmas-y as anything I have ever seen."

The only part of the Roosevelts' holiday celebration that seldom varied was New Year's Eve. FDR and ER usually marked the occasion with a White House dinner for family and friends and perhaps a movie or live entertainment in the early evening. In 1939, however, their routine was disrupted when two Washington teenagers, a boy and a girl, entered the mansion undetected in a quest to obtain FDR's autograph. (The White House staff admitted the couple thinking they were two other young people who were on the guest list but who had not yet arrived.) The boy, Joseph Measell, walked all the way up to the Third Floor where the Roosevelts and their guests were watching a movie before being accosted by the Roosevelts' youngest son, John. Measell explained his mission, and left the White House with autographs from FDR, ER and John.

That incident aside, the Roosevelts and their guests usually concluded their New Year's Eve celebration, by gathering in the president's White House study where they waited, eggnog cups in hand, for "the radio to announce the end of the new year and the beginning of the new one." As midnight struck, FDR would offer his traditional toast: "To the United States of America."