One of the earliest historical references to Highgate is in the grant made by Edward III. in 1363 to a certain William Phelippe, 'as a reward for his care of the highway between Highgate and Smithfelde, of the privelege of taking customs of all persons using the road for merchandize,' and it has been suggested that this Phelippe may have been one and the same with the 'nameless hermit' who preceded the holy man William Litchfield, to whom in 1386 the Bishop of London gave, to quote his own words, 'the office of the custody of our chapel of Highgate beside our Park of Hareng, and of the house to the same chapel annexed.' This chapel and hermitage were successively occupied by several recluses, the last of whom is supposed to have been a certain William Foote, on whom they were conferred in 1531. The dwelling-house was given in 1577, by Queen Elizabeth, to a favourite protégé of hers named John Farnehame, whose lease was later transferred to the founder of the 'Publique and Free Grammar School of Highgate,' Sir Roger Cholmeley, Lord Chief Justice of the King's Bench under Edward VI., who fell into disgrace with Queen Mary, and after suffering imprisonment for some years, lived in great retirement at Hornsey. Sir Roger obtained a licence to build a school, and Bishop Grindal gave him the old Hermitage Chapel, with two acres of land, under certain conditions, one being that the people of Highgate as well as the pupils should have the use of the chapel. It was to serve, in fact, as a kind of chapel of ease to Hornsey, an incidental proof that there were already at the time of the agreement a number of inhabitants in the hamlet of the Highgate. Sir Roger Cholmeley died before the projected work was begun, but his wishes were carefully carried out by his trustees, and the first stone of the institution, which was to have such a long career of usefulness, was laid in 1576.
It does not appear quite clear whether the old Hermitage Chapel was pulled down to give place to a new one, or enlarged to meet the needs of the increased congregation, but in any case the school chapel was the only place of worship in Highgate until 1834, when the parish was separated from Hornsey, and the fine Gothic church of St Michael, the lofty spire of which is a landmark for many miles round, was erected. Five years later the cemetery, that is still the most beautiful suburb of the dead near London, was consecrated, and since then many famous men and women have been buried in it, including the philosopher and chemist Michael Faraday; the eloquent writer Henry Crabb Robinson; the lawyers Judge Payne and Lord Lyndhurst; the artists John James Chalon, Sir William Ross, and John George Pinwell; the poet-painter Dante Gabriel Rossetti; the theologian Frederick Maurice; the novelists George Eliot and Mrs. Henry Ward; the pugilist Tom Sayers; and the no less celebrated cricketer John Lillywhite.
For many years the land round the old school chapel had served as a cemetery, and in it was buried in 1534 the poet Samuel Coleridge, who had lived for many years in Highgate, and when a year later the old school chapel was replaced by the present one, a beautiful Gothic building designed by Cockerell, it was wisely decided to erect the latter over the tomb, that is now enclosed in a crypt approached by a flight of steps from the western side of the building. The new schoolhouse, classrooms, etc., completed in 1869, that replace those that had been in use for some four centuries, and in which many men of note were educated, including Nicolas Rowe the dramatist, harmonise well with the chapel, and the institution bids fair long to maintain in the future the reputation it won in the past.
Highgate no doubt owed its early prosperity and rapid growth during the last hundred and fifty years to its situation at the junction of the two main roads from London that meet in the High Street, not far from the old village green, in the midst of which there used to be a pond, now filled in and planted with trees, round about which the village lads and lasses were wont to dance, and the elder residents to gather to gossip of a summer evening. Before the Bishop of London consented in 1386 to allow a road to be made through his park, Highgate could only be reached by a narrow lane, by way of Crouch End, Muswell Hill, and Friern Barnet, but the new thoroughfare very quickly became the chief highway to the north, and is associated with many noteworthy events and royal progresses. It remained, indeed, without a rival until the beginning of the nineteenth century, when an Act of Parliament was passed sanctioning a licensed company to make a way from the foot of Highgate Hill to join the main road, a principal feature of which was the piercing of a tunnel seven hundred and sixty-five feet long by twenty-four wide and nineteen high, which, alas, was but poorly engineered, for it fell in with a great crash before it was opened to traffic. The tunnel was then replaced by the present fine archway, spanning the road, that was completed in 1813, and for the use of which a toll was levied until 1876, when it was finally remitted.
Unfortunately the once beautiful village of Highgate has of late years been transformed into a somewhat prosaic suburb, but a few relics remain to bear witness to more picturesque days gone by. At the foot of the ascent, a little above the Archway Tavern, opposite the Dick Whittington public-house, is a railed-in stone supposed to occupy the exact site of the one on which the penniless boy, the future Sir Richard Whittington, rested, weary and worn from his long tramp on foot, and heard the bells ring out: 'Turn again, Whittington, thrice Lord Mayor of London Town.'
Within sight of this stone are the Whittington Almshouses, that represent those of the ancient foundation of Sir Richard in Paternoster Row, and were built in 1822 by the Mercers Company, as trustees of the Lord Mayor's will made in 1421, bequeathing the funds for erecting and endowing a college of priests and choristers, and building homes for thirteen poor men. With their picturesque chapel and general air of comfort, it must be owned that they contrast favourably with the ancient almshouses not far off in Southwood Lane, that were founded in 1658 by Sir John Wollaston, and added to seventy years later by Edward Pauncefoot.
Within the grounds of Waterlow Park, part of which was given to the public by Sir Sydney Waterlow, is the famous Lauderdale House, built about 1650, that was long the residence of the infamous Viceroy of Scotland under Charles II., the Duke of Lauderdale, who was probably often visited in it by his venial tool, Archbishop Sharp. To Lauderdale House the dissipated king brought the merry-hearted Nell Gwynn, and it was here that she is said to have forced her royal lover to acknowledge himself to be the father of her boy, the future Duke of St. Albans, by threatening to drop the child out of the window if he refused to do so.