The mountain was named for the outline of its ridge, which resembles a saddle, by Orson Schofield Phelps and Frederick Perkins.

[4] The earliest recorded ascent was made by amateur climber Newell Martin on August 5, 1894.

It was claimed that an earlier ascent was made by patent lawyer James J. Storrow and mountain guide Orlando Beede, but the date of this climb is unknown.

Beginning at the Garden parking lot west of Keene Valley, the Phelps Trail travels 3.5 miles (5.6 km) to the Johns Brook Lodge.

The State Range Trail begins at the lodge and continues 3.1 miles (5.0 km) to the col between Gothics and Saddleback, then turns up Saddleback for the final 0.6 miles (0.97 km) to the top.