Depicts an idealized portrait of Ira Allen, wears a periwig, and below his head appears his name.

Ira Allen (1751–1814) was one of the founders of the U.S. state of Vermont and a leader of the Green Mountain Boys during the American colonial period. He was the younger brother of Ethan Allen.

During the American Revolutionary War, Allen was a leading figure in the declaration of the Vermont Republic in 1777, which was originally intended to be independent of both the British colonies and the newly founded United States.

The Green Mountain Boys was a militia organization first established in the late 1760s in the territory between the British provinces of New York and New Hampshire, known as the New Hampshire Grants and later in 1775 as the Vermont Republic (which later became the state of Vermont). Headed by Ethan Allen and members of his extended family, it was instrumental in resisting New York's attempts to control the territory, over which it had won de jure control in a territorial dispute with New Hampshire.

Depicts a catamount, facing and walking to the left. The animal is virtually penned in with lettering, and the designer's initials, CK, between its rearmost paw and the end of its tail.

The Battle of Bennington was a battle of the American Revolutionary War, part of the Saratoga campaign, that took place on August 16, 1777, in Walloomsac, New York, about 10 miles (16 km) from its namesake Bennington, Vermont. A rebel force of 2,000 men, primarily New Hampshire and Massachusetts militiamen, led by General John Stark, and reinforced by Vermont militiamen led by Colonel Seth Warner and members of the Green Mountain Boys, decisively defeated a detachment of General John Burgoyne's army led by Lieutenant Colonel Friedrich Baum, and supported by additional men under Lieutenant Colonel Heinrich von Breymann.

The battle was a major strategic success for the American cause and considered the turning point of the Revolutionary War; it reduced Burgoyne's army in size by almost 1,000 men, led his Native-American support to largely abandon him, and deprived him of much-needed supplies, such as mounts for his cavalry regiments, draft animals and provisions; all factors that contributed to Burgoyne's eventual defeat at Saratoga. The victory galvanized colonial support for the independence movement, and played a key role in bringing France into the war on the rebel side. The battle's anniversary is celebrated in the state of Vermont as Bennington Battle Day.