Emphasized by an unnaturally bright sky, with his face catching the upcoming sun, stands General George Washington. The people in the boat represent a cross-section of the American colonies, including a man in a Scottish bonnet and a man of African descent facing backward next to each other in the front, western riflemen at the bow and stern, two farmers in broad-brimmed hats near the back (one with bandaged head), and an androgynous rower in a red shirt, possibly meant to be a woman in man's clothing. There is also a man at the back of the boat that looks to be Native American. The man standing next to Washington and holding the flag is Lieutenant James Monroe, future President of the United States. Also, General Edward Hand (commanding general at Siege of Yorktown) is shown seated and holding his hat within the vessel.

The painting contains an often-discussed historical inaccuracy: the flag in the painting had not yet been established at that time the painting was created. The flag depicted is the original flag of the United States (the "Stars and Stripes"), the design of which did not exist at the time of Washington's crossing. The flag's design was specified in the June 14, 1777, Flag Resolution of the Second Continental Congress, and flew for the first time on September 3, 1777, well after Washington's crossing in 1776. The historically accurate flag would have been the Grand Union Flag (Image 1), officially hoisted by Washington himself on January 2, 1776, at Cambridge, Massachusetts as the standard of the Continental Army and the first national flag. Artistic concerns motivated further deviations from historical accuracy. For example, the boat looks too small to carry all occupants and stay afloat, but this emphasizes the struggle of the rowing soldiers. There are phantom light sources besides the upcoming sun, as can be seen on the face of the front rower and shadows on the water, to add depth. The crossing took place in the dead of night, so there should have been little natural light, but this would have made for a very different painting. The river is modeled after the Rhine, where ice tends to form in crags as pictured, not in broad sheets as is more common on the Delaware. Next, the men did not bring horses across the river in the boats. Finally, Washington's stance, obviously intended to depict him in a heroic fashion, would have been very hard to maintain in the stormy conditions of the crossing.

At least three times in the 20th century, American grade school administrators stepped in to alter textbook reproductions of the iconic painting because Washington's pocket watch was painted too close to his crotch for their comfort, possibly resembling male genitalia. In Georgia in 1999, for example, Muscogee County teachers' aides painted out the timepiece by hand. In Cobb County, Georgia, the page with the offending reproduction was completely torn out.