The first petition for land ownership in Milkish was organized by a man named Peter Cox.

Peter Cox escaped slavery in Connecticut in 1780 and arrived in Saint John on the Aurora, a loyalist ship, in 1783. Cox arrived as the indentured servant of a loyalist named Thomas Rogers. Though technically a free man, Cox was effectively re-enslaved.

In 1784, Rogers posted a runaway advertisement in the Saint John Gazette, seeking the return of six slaves/servants: Peter Cox, Edward & Charity Morris and their child, and Andrew and Eanus Bush. In his notice, Rogers also sought punishment for a "Mr. Dibble," who aided their escape. This likely refers to Fyler Dibblee, a prominent member of the Kingston Dibblee family.

Cox then moved to Milkish, where a large number of black refugees likely already lived. In 1785, he filed a petition on behalf of himself and twenty-two other black refugees. This petition was granted.

The second petition for land ownership in Milkish was organized by a man named Moses Simpson.

Like Cox, Simpson escaped slavery in the United States. Unlike Cox, Simpson was not re-enslaved in Saint John. In fact, records show that he was granted a residential plot in the city by 1784.

In 1785, Simpson filed a petition for land in Milkish along with fourteen other men. This petition was also granted, meaning that at least thirty-seven black men had the right to work land in Milkish by the end of 1785.

In 1787, Simpson filed another petition on behalf of these men requesting additional time to work their land grants in Milkish. It seems that a local land surveyor had recently ordered a number of black men to stop working their land, claiming that they no longer had right of possession.

In October 1787, Lieutenant Governor Carleton denied this request. Instead, he ruled that “Those of the Blacks who hold possession and cultivate their Lots will have Grants – The vacant Lots will be granted to the first Cultivaters.” According to legal standards, almost no lots were effectively cultivated, meaning that the vast majority of black people in Milkish no longer held possession.

After losing his land in Milkish, Simpson continued his struggle. He moved to St. Anne's Point, now Fredericton, and petitioned for land there. When his petition was won, he became the first black man to be granted land in the city.

Carleton’s ruling allowed men who managed to cultivate their land to government standards to maintain possession of it. Though it is unclear how many people in Milkish qualified, it is possible that at least one of the original petitioners, William Lorraine, was able to successfully retain his land during this period.

William Lorraine appears on Peter Cox’s petition in 1785. Several years later, a William Lorraine was still living on land that had been allocated to black settlers. In 1788, this man was granted an additional two-hundred acres of land.

It is unclear if the William Lorraine in Milkish in 1788 is the same man who petitioned for land with Cox. His 1788 petition for land was supported by men who initially seemed to resist black settlement in Milkish, including the land surveyor.

The specific wording in the letter of support also seems to imply that Lorraine was not black; however, the name William Lorraine was not common in New Brunswick at this time, making it unusual for two different men of the name to petition for land in Milkish within three years.

Another case that sheds light on the story of Milkish is that of Benjamin Johnston and Henry Borum. Johnston and Borum worked in the Kingston and Springfield area and petitioned for land in the Parish of Springfield decades after the dissolution of the land grant.

Johnston and Borum persevered for years and had the full support of some of the most powerful men in Kings County but were unable to successfully obtain land from the government.

Johnston and Borum's petitions were actively supported by eight Justices of the Peace and Judge David Pickett. Kingston community members who lent their support to Johnson and Borum included Sheriff Walter Bates and Reverend Elias Scovil, and one letter of support was signed by fourteen different people from prominent local families.

Still, the land grant system prevented these two men from obtaining land ownership. In the end, the land that they sought was granted to less suitable white farmers.