Toby Caulfeild, 1st Baron Caulfeild
Sir Toby Caulfield, 1st Baron Caulfield of Charlemont (1565–1627) was an English army officer active in Ireland.
The son of Alexander Caulfield of Great Milton in Oxfordshire, he was born 2 December 1565. When a youth he served under Martin Frobisher, and then under Lord Howard of Effingham. He was also with Robert Devereux, 2nd Earl of Essex at the capture of Cadiz, 21 June 1596.
In 1598 Caulfield accompanied Essex to Ireland, in command of a troop of horse, and was for a time stationed at Newry. In 1601, under Lord Mountjoy, he took part in the capture of Kinsale from the Spanish forces. Mountjoy left Caulfield in charge of a bridge built by him over the River Blackwater, in command of 150 men, where the fort erected for its protection was called Charlemont.
After the accession of James I of England, Caulfield was knighted. After the Flight of the Earls of 1607, he was appointed receiver of the rents of Hugh O'Neill, Earl of Tyrone, until 1610. On the division of the estates, Caulfield received a grant of a thousand acres. He had, in 1608, been appointed to the command of the upper part of Tyrone and of Armagh. On 17 April 1613 he was named a privy councillor, and the same year he was chosen knight of the shire for Armagh. in the Irish Parliament. On 19 February 1615 he was made master of the ordnance, and on 10 May of the same year one of the council for the province of Munster. Subsequently he was appointed a member of the commission for the parcelling out of escheated lands.
In consideration of his services to the crown, Caulfield was created Baron Charlemont, and as he had not married, the succession of the honour was granted to his nephew, Sir William Caulfield, son of his brother James. He died 17 August 1627, and was buried in Christ Church Cathedral, Dublin.