Hamilton Hall was named after the nation's first Secretary of Treasury and father of the U.S. Coast Guard, Alexander Hamilton. Needing to generate funds to support the young nation, Hamilton proposed the establishment of a Revenue Marine Service in April of 1790. On August 4, 1790, Congress passed Hamilton's Revenue Cutter Bill, which called for the construction of ten boats. This Revenue Cutter Service grew and acquired a multi-mission role in our nation's military until merging with the U.S. Life-Saving Service in 1915 to form the U.S. Coast Guard. Hamilton Hall houses the offices of the Superintendent, the Dean of Academics, Public Affairs and other administrative offices. When Hamilton Hall was first built in 1931 the second deck was the Officer's Mess and a Sick Bay.

Henriques Room was named after, Captain John A. Henriques, the first Superintendent of the Academy. Captain Henriques (b.1826 - d.1906) joined the Merchant Marine in 1841, and enlisted in the Revenue Marine in 1854. Henriques was selected to run the first cadet training ships, the Dobbin and Chase. He also served as Superintendent of the Revenue Cutter School of Instruction (today's Academy precursor) until 1883. During the Spanish American War of 1898, he served on the Woodbury. Captain Henriques died in 1906 and is buried in Cedar Grove Cemetery in New London, Connecticut. The Henriques room was originally the Academy library, and is now used for special gatherings and award ceremonies. Aldis Browne, graduate of Yale School of Fine Arts, worked for the U.S. Treasury Art Relief Program during the Great Depression and completed the various murals painted on the walls. The murals represent the Coast Guard's history. The room is also filled with museum artifacts.

Flagpole
The flagpole in front of Hamilton Hall is a replica of the mast from the Academy training ship Alexander Hamilton. This area is supposed to resemble a quarterdeck, the most highly honored place aboard a ship. The shrouds leading to the top of the mast used to have ratlines. Upper-class cadets used to make fourth class cadets perform up-and-over drills. Basically climbing to the top of the mast over the yardarm and back to the deck as fast as possible. The Revenue Cutters first displayed the Coast Guard Ensign in the 1790s to identify them as federal law enforcement vessels. The Superintendent's flag is also flown when he is onboard the Academy.