On October 30, 1958, First Lady Mamie Eisenhower decorated the White House for Halloween for the first time. She hosted a lunch for the wives of staff members in the State Dining Room of the White House. Decorations included skeletons hanging from the wall lights, yellow jack-o'-lanterns, and shocks of dried corn in the corners of the room, and State Dining Room columns that were decorated at their bases with brown corn stalks, pumpkins, and red apples. The tables had miniature witches on broomsticks and 16 silver bowls filled with yellow and bronze chrysanthemums. Scattered on the tables were autumn leaves and autumn nuts, ears of dried corn, as well as dried gourds and dried squash. Black cats, black owls, disembodied witch heads, and goblins hung from the chandeliers in the foyer.

With the arrival of young children at the White House, Caroline and John Jr., during the John F. Kennedy administration, Halloween photographs emerged of the children crashing the Oval Office in their costumes. Since that time, first families have observed the holiday by hosting a Halloween event accommodating trick-or-treaters and a private family party with friends and staffers. Larger events have been held on the grounds of the White House for Halloween ever since, especially by first families with younger children, such as Amy Carter, Chelsea Clinton, and Malia and Sasha Obama.

Halloween took on a large significance during the Richard M. Nixon administration, as the first family hosted a series of public events for local children. In 1969, 250 local children from the Widening Horizons program came to a White House Halloween party. The North Entrance to the White House was converted into the mouth of huge 17-foot high pumpkin. Once the visitors walked through, two witches stirring cauldrons awaited, handing out masks. Tricia Nixon, dressed as a gypsy in a purple and green gown with a purple harlequin mask, welcomed the children and their parents. The East Room was bedecked with balloons and filled with sideshows of clowns, magicians, fortune-tellers, puppeteers, and apple bobbers. Jonathan Frid, the vampire Barnabas Collins from the popular daytime soap opera Dark Shadows, was a special guest and in costume and character. In 1971, First Lady Patricia Nixon, dressed as a gypsy, hosted an early Halloween party for 150 children from the C. Melvin Sharp Health School and Hospital for Sick Children. Characters from the Disney on Parade show appeared and entertained the kids. In 1972, Tricia Nixon Cox hosted a Halloween party for 200 foster grandparents and their foster grandchildren, complete with circus clown Emmett Kelly, Jr., trained dogs, and chimpanzees from the popular TV series Daktari.

In 1977, Amy Carter celebrated her birthday at the White House with a Halloween theme party with 14 of her friends. The partygoers carved pumpkins, ate hamburgers, vanilla cake, and chocolate ice cream, and watched the original version of Frankenstein in the White House theater. In 1978, the Carters hosted a Halloween party for 600 staffers and their spouses or dates. A 16-foot jack-o'-lantern built of gypsum and plywood was put up at the North entrance door. Costumes were optional, but several witches and a World War I flying ace were on hand. Broadway star Carol Channing provided entertainment and Carmino Ravosa performed his one-man musical, Ghosts of the White House, featuring Abigail Adams, Thomas Jefferson, and John Tyler.

On November 1, 1982, the Reagans were greeted by a pumpkin located on a table by the door carved with the slogan "Stay the Course." The election was the next day, November 2.

The Bushes hosted a Halloween party for 600 schoolchildren on the South Lawn in 1989. President Bush joked with them, "How many of you guys believe in ghosts? How many? You know, they say that there's a ghost in this old house. And the most famous one, you know, is Abraham Lincoln. And Barbara and I haven't seen the ghost of Abraham Lincoln walking the halls, but this is our first Halloween in the White House, so maybe we'll see him tonight."

The Clintons held annual Halloween costume parties for friends and staff and, as the first lady's birthday was October 26, often combined the celebrations. One of their most memorable costumes was their appearance as President James Madison and First Lady Dolley Madison at the 1993 Halloween Party in the East Room of the White House.

The Bushes enjoyed featuring their pets Miss Beazley, Barney, and India in their costumes on Halloween cards and photographs. In 2007, the cat India was a wizard; and Scotties, Miss Beazley, a strawberry, and Barney, a cowboy.

The Obamas have welcomed trick-or-treaters from local schools and the children from military families every year except 2012 when Superstorm Sandy hit the East Coast. At their first Halloween at the White House in 2009, the Obamas handed out goody bags with presidential M&Ms, cookies, and dried fruit to 2,000 children. Many of the children, dressed as superheroes, pirates, and fairies, were greeted by President Obama in casual attire and First Lady Michelle Obama, who wore furry cat ears and a leopard top.

President Donald J. Trump and First Lady Melania Trump hosted trick-or-treaters every year at the White House, inviting local schoolchildren and military families onto the White House Grounds. Their exterior decorations consisted of large spiders and webs, pumpkins, haystacks, corn stalks, and spooky tree branches.