By the mid-1800s, tourism on the mountain flourished. Train service was extended into the White Mountains, and a bridle path was opened to the summit that made it accessible to tourists who were flocking to the area. The first hotel, the Summit House, was built in 1852, just feet from the highest crag of Mount Washington. The rugged stone hotel was so successful its first year of operation that a competing hotel, the Tip Top House, was built the following year.

At the time the hotels were built, the only access to the summit was by foot or on horseback. It is hard to imagine how difficult and time-consuming the building of the hotels on the summit of Mount Washington must have been. Other than the stones that were abundant on the summit, all the materials had to be hauled nine miles by horses over rough trails. In addition, the workers had to climb to work each day from a camp two miles down the mountain.

Walls of the Tip Top House were made of stone blasted from the mountain rock. The original roof was flat, and used as an observation deck. In clear weather, a telescope with a tripod was put on the roof for the enjoyment of visitors. The flat roof of the Tip Top House was replaced with a pitched roof in the early 1860s.

An exciting new era began for Tip Top House in 1877 when it became the first printing office for the newspaper, Among the Clouds, that was printed on the summit. For seven years the printing presses in Tip Top House whirred out the summit news for visitors. Once production of the newspaper was moved to a separate building on the summit, Tip Top House was abandoned and allowed to fall into disrepair.

Development at the summit continued, and included a three-story, 91-room hotel, a daily newspaper, and a weather observatory. The great fire of 1908 destroyed the "City Among the Clouds," sparing only the Tip Top House. The sturdy building was renovated to once again serve as a hotel, as it was the only structure left to provide accommodations and meals for visitors. Shortly after completion of the new Summit House, the Tip Top House itself was destroyed by fire. It was rebuilt amd used as a Summit House annex. Much in need of repair, its long history as a hotel ended when it was abandoned in 1968.

Now a state historic site, Tip Top House is once again open to summit guests. As a result of the most recent restoration which was completed in 1987, the building now resembles the original house as it was when it was first built with a flat roof. As the sole summit survivor, it provides a link between the mountain's past and present and affords a window to its rich history. The Tip Top House is believed to be the oldest mountain-top hostelry still in existence in the world.