Born in Essex, Westwood had already served one year in prison for highway robbery before his transportation at age 16 to the penal colony of New South Wales on a conviction of stealing a coat.

He arrived in 1837 and was sent to Phillip Parker King's station near Bungendore as an assigned servant, but grew to resent working there due to mistreatment from the property's overseer.

The following year, troopers captured Westwood at Berrima, where he was convicted of armed robbery and horse stealing and sentenced to life imprisonment at Darlinghurst Gaol.

Sent to Cockatoo Island, he led a failed mass escape, and was transported for life in 1842 to Port Arthur, Van Diemen's Land.

His new bushranging career ended that November when he was captured and sentenced to twelve months' hard labour and solitary confinement.

The following year, William Champ, Port Arthur's new commandant, promoted Westwood to his boat crew, and approved his removal to Glenorchy on probation after the convict rescued two drowning men.

Within several months, he returned to bushranging, and after his capture in September 1845 outside Hobart, was transported for life to Norfolk Island.

[1] In the days before his execution, Westwood wrote an autobiography at the suggestion of Thomas Rogers, a religious instructor, who later had it published in The Australasian.

On 10 March 1835 William and Benjamin Jackson, both aged fourteen, appeared at the Essex Lent Assizes in Chelmsford charged with highway robbery.

Westwood and Bird took the stolen coat to a clothes shop owned by John Warner in Hare Street, Hertfordshire where they sold it for 6 shillings.

On 2 February 1837 William was delivered to the prison hulk Leviathan in Portsmouth Harbour where he was held before being transferred to the ship Mangles which sailed for NSW on 18 March 1837.

He mainly stole racing horses (to ensure a quick getaway), clothing, guns, ammunition, money, and necessities of living.

A carpenter named Waters also joined in the attack, and felled the bushranger by a blow on the head with a shingling hammer, and then captured him.

Escaping for a short period he succeeded in evading the police and was not heard of again till he called at the toll gate on the Parramatta road, about three miles out of Sydney.

On Tuesday evening, 13 July 1841, Westwood entered Edward Gray’s Black Horse Inn, near the crossroads ten miles from Berrima.

He took charge of the firearms at the inn and had ordered the till to be taken out when he was set upon by the publican Gray and two other men, a ticket-of-leave holder named Francis McCrohan and Joseph Waters, an assigned convict.

While at Cockatoo Island, he and twenty-five other convicts, attempted to escape by swimming to the mainland, but the gang were followed by the police in their boat and all captured.

In February 1844, Major Joseph Childs took over the command of the convict prison settlement at Norfolk Island where he began a regime of harsh, rigid discipline that ended with mutiny, massacre, and the execution of 12 men.

He had looked on his prisoners as human beings and had given them some little interest in life by allowing them to have small farm plots in which they could grow sweet potatoes and other vegetables.

Maconochie also shortened hours of labour, holidays were granted to those convicts whose behaviour was considered satisfactory, and each prisoner was allowed to cook his own meals in saucepans and kettles specially provided.

Gathering in rough military formation they marched to the Barrack Yard, stormed the store, and seized every utensil within reach.

The convicts moved on in a wildly rushing mass about 1,600 strong, to the Barrack Yard gate, where they pushed aside a sentry and an overseer who tried to halt them.

As though the force of their passion had suddenly been spent, the convicts halted, and then began to retreat towards the lumber yard, where their weapons were taken from them, and they were returned to their cells.

In 1844, Melbourne writer Thomas McCombie published a supposedly true-life account of Westwood in Tait's Edinburgh Magazine.