Planter and merchant
Scarborough was one of the most prominent of the English settlers in Accomac Shire of the Virginia colony, in what is now the Eastern Shore of Virginia. The land on which his main residence, Occahannock House was constructed, was acquired on this man's behalf when he was a seven year old boy. In November 1634, Scarborough repatented land on Maggoty Bay claimed by his father for transporting his wife, son and a servant to the colony, and began claiming land in his own right.
In 1653, Scarborough was barred from public office and asked to leave the Virginia colony because of his strident Royalist sympathies, whereupon he departed after leasing 3000 acres patented in the names of his sons and four ships to William Bunton of Boston, the lease expiring in 14 years when Edmund Jr. was to come of age. In 1654 he and John Walton invested in 3,900 acres called "Peckincke" in Westmoreland County on behalf of John Bagnall of London.
Scarborough was a merchant whose ethics many questioned. Beginning in 1660, he also operated salt works at Occahonnock House and at Gargaphia nearer Maryland, but had not achieved the volume the legislator required for a bonus by 1666. Scarborough also had a fleet of ships traded with other colonies, including buying enslaved people from Angola in New York and transporting them south for resale. By December 1662, Scarborough owned slaves at Occahonnock House and also employed a tanner, four shoemakers (in June but nine in December) and two coopers. During the First Anglo-Dutch War, one of Scarborough's ships was seized en route to other colonies for trade. He retaliated by seizing a Prussian ship of similar size, although it was not of Dutch ownership. In 1652, Scarborough sold his seven ships (Deliverance, Mayflower, King David, Sea Horse, Holly Horse, Ann Clear, and Artillery) to William Burton of Boston.
Trained as a lawyer, Scarborough gained a reputation for ruthlessness by incidents such as that involving Anthony Johnson, a free black man. In 1657, Scarborough forged a letter in which Johnson, although illiterate, acknowledged a debt. Johnson could not contest the case; nevertheless, the court awarded Scarborough 100 acres (40 ha) of Johnson’s land to pay off his alleged "debt".