On September 8, 1814, the Madisons moved into the Octagon, second in size only to the burned President's House, and the only private home in Washington with the requisite elegance and scale for grand entertaining.

Designed by William Thornton, the Octagon was built in 1800-01 as a winter townhouse for Colonel John Tayloe III, a wealthy Virginia planter and horse breeder. An agreement was made for a rental fee of $800 for six months and President Madison set up his office in the circular study on the second floor.

The Madisons held their first Wednesday evening levee at the Octagon on September 21. Resentment toward the president gradually waned and crowded receptions at the Octagon began to resemble the famed White House "squeezes." On March 5, 1815, First Lady Dolley Madison wrote to Hannah Gallatin: "Still our house is crowded with company. [I]n truth ever since the peace my brain has been turn'd with noise & bustle. Such over flowing rooms I never saw before—I sigh for repose."