Sir Hugh Willoughby (fl. 1544; died 1554) was an English soldier and an early Arctic voyager. He served in the court of and fought in the Scottish campaign where he was knighted for his valour. In 1553, he was selected by a company of London merchants to lead a fleet of three vessels in search of a Northeast Passage. Willoughby and the crews of two ships died on the voyage while the third vessel , under the command of Richard Chancellor, went on to open a successful, long-lasting trading arrangement with Russia. Biography Willoughby was the third and youngest son of Sir Henry Willoughby of Middleton, Derbyshire, a wealthy and influential gentleman who served in the courts of Richard III and Henry VII and was knighted by Henry VII following the Battle of Stoke Field in 1487. Hugh Willoughby served various roles in the court of Henry VIII and then joined the military to serve as a captain in the Scottish campaign of 1544. He was knighted at Leith by Edward Seymour, 1st Duke of Somerset, then Earl of Hertford. In February 1548 he was sent with Thomas Carlisle and 50 horsemen by Grey of Wilton to capture "Billie tower". He became commander of the fort on the site of Thirlestane Castle and served there until 1550, successfully withstanding a siege by the Scots and the French. In 1551 he was again campaigning in the border country and eastern marches. The downfall and execution of Somerset in 1552 affected Willoughby's standing and caused him to look for other opportunities. In 1553 a company of London merchants and courtiers were financing a voyage of exploration and trade. Organized by Sebastian Cabot, they hoped to find a northeast sea route to the Far East. Initially called the Company of Merchant Adventurers to New Lands, the trade organization became better known as the Muscovy Company. Willoughby petitioned to lead this expedition and although he lacked significant maritime experience, he was selected based on his distinguished family and his "singular skill in the services of war." Three new vessels were constructed specifically for the voyage; on one ship the keel was lined with lead in hopes of preventing attack by shipworms. The fleet was well-provisioned for a lengthy voyage and an experienced crew was selected. On 10 May 1553, Willoughby set sail on the Bona Esperanza as captain-general of the fleet with two other