The flags encased at the east end of Annenberg Hall replicate those of the 20th Regiment of Massachusetts, often called "The Harvard Regiment" because of the large number of its officers educated here. Two of the flags were given to the regiment upon its inception in 1861. They are noteworthy as the regiment's first official "colors." The third flag was presented to the regiment later in 1861 to commemorate the disastrous battle of Ball's Bluff in which 195 of the regiment's 300 men suffered casualties.
Due to their fragile condition, the original flags were removed during the 1994 restoration to an off site, climate controlled environment. The museum quality replicas now on display were constructed of silk taffeta and hand painted by Steven Hill of Boston in 1995.