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St. Leonard's Church in Watlington lies on the outskirts of the town: it is built of flint with stone dressings, and comprises a chancel, nave of four bays, north and south aisles, a south porch, a south chapel, a vestry, and western tower. Apart from the tower it was almost entirely rebuilt in 1877 in the Decorated style.

There seems to have been some uncertainty in the past about its dedication. Rawlinson stated in 1718 that it was dedicated as St. Bartholomew or St. Mary the Virgin, and the town fair was certainly held on St. Bartholomew's Day. An early-19th-century historian of Watlington, John Badcock, gave its dedication as St. Mary. In the early 14th century, however, it was undoubtedly dedicated to St. Leonard. 

Some remnants of an earlier Romanesque church are preserved in the present building: in the east wall of the organ-chamber there is the diapered tympanum and plain arch of an outer doorway which was in the north wall of the nave before the north aisle was added; in the south wall of the choir there is a small column with a Romanesque capital; and in the west wall of the south aisle are two small capitals of the same period.

Nineteenth-century drawings made before 1877 show that the church was built mainly in the style of the late 14th century. Of the medieval structure there survive the battlemented west tower, the south nave arcade, the walls of the south aisle, and the south wall of a chapel on the south side of the chancel. This chapel was added about the end of the 15th century. According to the inscription on a brass stolen by a parish clerk, but recorded by Rawlinson, Maud, the wife of Richard Warner, woolman, was the foundress of this chapel. The year of her husband's death is unknown, but it is possible that he was the father of Robert Warner who died between 1478 and 1495, and that Maud erected the chapel as a memorial to him. The Perpendicular window in the south wall and the two bays of Perpendicular arches on the north side might well have been constructed in the mid-15th century. The east wall of the medieval chapel was where the 19th-century arch now is, and the eastward extension was made in the 18th century. The Decorated window, of which only the upper half remains, that is now in the east wall of the 18th-century extension seems to be of about the same date as the east window in the chancel. It is likely that it was originally in the south wall of the chancel, was moved when the chapel was built and reused in the chapel's east wall, and again reused when the chapel was extended in the 18th century. It is shown in 19th-century drawings of the church made before the restration of 1877. 

No record has survived of any 16th- or 17th-century work. In 1721 a number of paving and building bricks were paid for, so repairs to the floor were evidently carried out. In 1743 Thomas Stonor ordered the whole pavement and steps of the chancel to be taken up and 'levelled and layd down with new pavement' and 'new facing of stone to the steps.' He also ordered the tiling to be completely repaired. He examined the roof of the chancel and could not find that it had ever been ceiled; he agreed with the bishop that he was not obliged to add 'what for so many ages has never been thought necessary', but nevertheless gave orders for the chancel to be ceiled. He also agreed to put in a new east window. If this was actually done the new window must have been a copy of the old one for 19th-century drawings show a Decorated east window. It was complained at the time that the churchwardens and leading men of the parish showed little regard for 'decency and beauty in their church', and in 1759 the archdeacon ordered that the pavement should be 'new laid' in many places and that no burials should take place in the church unless a brick arch was built over the grave. The chancel was to be whitewashed.

In 1763 Edward Horne, member of a leading family of tradesmen and landowners in and around Watlington, petitioned for a licence to carry on the south wall of the church until it became even with the east end of the chancel and to cover the roof with lead. The dimensions of the vault were to be 19 ft. by 15 ft. The work was carried out as the present measurements of the eastward extension show. Externally, a buttress against the south wall marks the junction of the 15th-century wall with its 18thcentury extension. The vault was entered by a large iron gate placed in the original east wall of the chapel. There was no direct entry from the vault into the chancel, the south wall of which was left intact. From an early-19th-century drawing and description of the mausoleum it appears that the Horne memorial inscriptions were arranged on white marble shields; that the mausoleum was about 8 feet high, contained eighteen compartments, and was placed under the east window. The interior of this vault was largely rebuilt in the course of the 19th-century restoration.

The only other information about the church before its restoration concerns its internal fittings. In 1681 Mr. Deane (i.e. Simon Adeane, d. 1686) promised to refloor the women's seats which were next to the 'parsonage' seat. He himself was to have the uppermost seat next the minister and permission to make a pew there. He also promised to wainscot the wall from the reading pew to the belfry and repair all benches or seats that were broken. In the next century growing population led to the building of galleries by the gentry and better-class tradesmen: in 1704 Richard Lamborne and Francis Nash petitioned to build a gallery (12 ft. × 12 ft.) on pillars; in 1723 the vicar, Thomas Toovey, asked for one; and in 1738 when Mr. John Duncombe petitioned for yet another it was stated that Mr. Horne had one, 'handsomely adorned and beautified with carved work' which was 'ornamental to the church' and would be obscured if Duncombe's was erected in the proposed spot. A few years later Ralph Towney, a draper, wanted a gallery near the singers' one. The singers' gallery was a public one and had been paid for by subscription. Meanwhile, the church was otherwise somewhat neglected. In 1743 the Lord's Prayer and the 'Belief' were reported out of repair; there were no Commandments; and the font had not been moved in accordance with Bishop Secker's wish. The purchase of the existing beautiful chandelier, now in the south chapel, from Mr. Cooke in 1778 marks a revival of interest. In 1781 the king's arms were painted by Mr. Chapman for £13 13s. In 1808 a new font was installed near the south door, the old one having been broken when it was moved in 1806; it was made by Hudson of Oxford for £13 17s. and was a 'Gothic stone font with marble bason and top compleat, carved dove etc.'. Payments were made in 1806 and 1808 to Mr. Chapman for rewriting the Commandments, the 'Belief', and the Lord's Prayer, and the inscriptions on the monuments of the donors of charities; and in 1815 a new window at the west end of the church cost £5 1s. 4d. In 1817 Robert Exton new-faced the two outer doors on the south side of the church 'in Imitation of antient Gothic work'. 

In 1842 the vicar and churchwardens petitioned the 'Society for the Enlargement of Churches' for a grant to extend the church, and it was probably at this time that unsigned plans by an architect, now in the parish chest, were made, but nothing came of this scheme and it was not until 1874 that restoration was undertaken. The curate-in-charge, Arthur Lloyd, and his churchwarden William Wiggins, were the chief promoters of the work; the architects were H. J. Tollit of Oxford and Edwin Dolby of Abingdon. The builder was Martin of Hereford. The nave and chancel were reroofed, a north aisle, vestry, and organ chamber were added. The wall of the south aisle was heightened and a south porch was built. The south aisle was reroofed and the first two windows counting from the west were rebuilt. A 14th-century cusped tomb recess was preserved in the south wall. The south doorway into the 15th-century chapel, shown in Buckler's drawing of 1822, was blocked up. The Horne vault to the east of the south chapel was remodelled. A window was inserted in the south wall and arches were made between the vault and the chancel arch and between it and the south chapel. All the other windows in the church were repaired.

A considerable amount of work was done on the interior: the galleries at the west end and over the south aisle were removed. The Horne mausoleum in the south chapel was taken down and the iron gates which inclosed the entrance to it were removed, although the original petition for a faculty stated that these were to be preserved. The Horne memorial tablets were reset in the south wall of the chapel; the altar rail, pulpit, and reading-desk were renewed. All the old seating was removed, except for the oak seats in the chancel, and the church was repewed. The reopening took place in March 1875, but the work of restoration was not completed until 1876. In 1877 the Diocesan Church Building Society was asked for a further grant, as £400 had had to be borrowed. 

Some further work was done to the fabric in the 20th century. The pinnacles of the tower were blown off in 1906 and 'the design of 1873 by Mr. Dolby' (i.e. Edwin Dolby of Abingdon), which was not carried out because of lack of funds, was completed. The architects Tollit and Lee of Oxford supervised the new work. 

In 1913 it was proposed to insert dormer windows in the roof to give light and ventilation, but the outbreak of war prevented the scheme being carried through. Electric lighting was installed in 1937, and in 1957 the stone steps and surrounding stonework were made in the choir. 

During the two decades after the restoration, much effort was spent on beautifying the restored building, particularly in the insertion of stained glass windows. Only a few fragments of medieval glass remained. These are now in the vestry and they include a shield with half the arms of Stonor in the dexter, which is thought to have represented originally the marriage of Sir Richard Stonor with Margaret, daughter and heir of Sir John Harnhill (Glos.). It was in the east window, certainly as late as c. 1750, and was replaced in 1887 by glass by C. E. Kemp, which was dedicated as a memorial of the golden jubilee of Queen Victoria; in the same year the stained glass in the east window of the south chapel, also designed by Kemp, was inserted in memory of the Revd. William Hulton who was lord of the manor; and the window of St. Paul of Athens in the north aisle in memory of a curate was made by Messrs. Atkinson of Newcastle. Stained glass in the west window of the tower, also by Kemp, commemorates the Revd. Basil T. S. Carter (vicar 1886–96). Three more windows each of two lights by Kemp were placed in the south aisle and dedicated in 1902.

Besides stained glass Kemp designed in 1889 the carved oak reredos, now on the south wall of the south chapel, but originally in the sanctuary. In 1897 Messrs. Blackler & Sons made a new alabaster and marble font to commemorate the diamond jubilee of Queen Victoria. They also made a low screen for the sanctuary with ornate brass gates, which was taken down in 1948 as it had become unsafe. 

A new screen was erected in the south aisle in 1903 and in 1904 the church acquired new clergy stalls in the choir, made by Whippell & Sons of Exeter. The stalls were the gift of the Revd. S. C. Saunders and his wife. Saunders also gave in 1905 the organ at a total cost of £1,000. It was built by Hill & Sons of Islington. The rood was erected to Saunders's memory after 1914; a clock by Smith & Son of Derby was placed in the tower in about 1914; the present high altar and panelling in the south chapel were given in memory of Annie Wiggins (d. 1926): they were designed by C. O. Skilbeck of Bledlow; and the lectern was given in memory of Marion Gunston in 1896.

The church also possesses an ancient parish chest; an oil painting, presented to the church in 1906, which is considered a copy of an altar piece by Annibale Carraci, some fine sets of modern vestments and copes, and a finely worked banner done by some ladies of Watlington and completed in 1957.

There are three brasses: William Frankleyn (d. 1485), his wife Sibilla, and four children; William Gibson (d. 1501) and his wife Maud, who are represented in shrouds; and Jerem Ewstes (Eustace), yeoman (d. 1587), who was the eldest son of Robert Ewstes and donor of the treble bell. He is depicted in doublet, hose, and short cloak. His inscription also states that his brother John (d. 1588) was buried with him. A fourth brass once in the south chapel is now missing. It was to Richard Warner, woolman, and his wife Maud, 'foundress of this chapel'. 

Memorials to the following are still in the church: William Buckland (d. 1597/8), yeoman; Robert Parslowe (d. 1683); Thomas Toovey (d. 1719), son of Thomas Toovey, vicar; Anne Burt (d. 1730), relict of Edward Burt; Mr. Richard Hester (d. 1736); John North, gent. (d. 1763); John Tilson (d. 1779), only son of George Tilson Esq., Under Secretary of State to Queen Anne; Richard Birkhead, vicar (d. 1784); George Tilson Esq. (d. 1795), son of John Tilson; the Revd. James Relton (d. 1795), Vicar of Shirburn; Thomas Barnes (d. 1829); George Hester (d. 1833); General Christopher Tilson Chowne (d. 1834), son of John Tilson of Watlington Park; John Henry Tilson (d. 1836), magistrate and eldest son of John Tilson; William Hester Wiggins (d. 1840); William Cozens (d. Feb. 1844); Robert Cozens (d. Dec. 1844); Daniel Burton (d. 1865); Moses Wiggins (d. 1878); Arabella Annie Wiggins (d. 1926); John Morris (d. 1938), physician; A. E. Snow (d. 1945), vicar for 22 years.

The south chapel contains many memorials to the Horne family, including the following: Edward Horne (d. 1765), son of Edward and Frances Horne; Charles Horne (d. 1772); Edward Horne (d. 1777), son of Samuel Horne, merchant of London; Samuel Horne (d. Jan. 1777); John Yardley Horne (d. 1789), son of Edward Horne and his wife Sarah; Samuel Horne, 3rd son of Samuel and Jane (d. 1797). These and other memorials (e.g. to Edward Horne, gent, (d. 1745), and his wife Frances (d. 1740), daughter of Richard Cornish), were once fixed to a mausoleum below the east window erected in 1765 by two sons of Edward and Frances Horne. It was removed at the restoration of the church.

The following monuments and inscriptions have been lost or are not now visible: a brass in the south chapel, already mentioned, to Richard Warner, his wife Maud, and their sixteen children; Edmund Wadbury the younger (d. 1513) and his wife Jane; Mr. Anthony Mollynes (d. 1582), his wife Agnes (d. 1610), and two children, also in the south chapel; Sir George Simeon, Kt. (d. 1665); Simon Adeane Esq. with arms (d. 1686); Ralph Wells, vicar (d. 1681); John Ovey (d. 1694/5) and son-in-law Richard Lamborn Esq.; John Greendown, surgeon (d. 1700); and Thomas Cornish, vicar (d. 1711). 

The medieval church had five bells, but none survived after 1663. The new bells were inscribed as follows: (1) Thomas Stonor Esq., Symon Bartlett, Thomas Gregory, C.W.H.K. 1663; (2) Jeram Eaustas [sic] gave this bell in 1587 H.K.: (3) Simon Bartlet [sic], Thomas Gregory, W.C.C.W. 1663; (4) Feare God 1635; (5) Prayes ye the Lord 1635; (6) Feare God, Honour the King 1660. Between 1736 and 1743 the bells were rehung on a new frame; in 1785 the fifth bell was recast by C. I. Rudhall and a new frame was again made, at a total cost of some £90; in 1867 £62 15s. was paid for a seventh bell. A faculty for two bells was obtained in 1905: one new bell was paid for by subscription and the other out of Mrs. Maria Cook's and Mrs. Whetton's charity; both were cast by Messrs. Mears & Stainbank. All the bells were hung on a new frame.

At the time of the Edwardian inventory the church seems to have been not far behind Thame in the richness of its possessions. These included satin copes, vestments of damask, and cloth of tissue flowered with gold; altar cloths, pillows, a corporal of cloth of gold with the five wounds on it, and a canopy with four staves. There were two silver chalices and patens, and many other silver and gilt items. Again, like Thame, Watlington church had a pair of organs and as at Thame its churchwardens seem to have forestalled the king's commissioners by selling some of the church goods; two chalices and a ship of silver were sold for £10 11s. and apparently other items as well for twelve more entries are missing. The present silver includes an Elizabethan chalice with no hallmark; a paten with the arms of Adeane impaling Whorwood (1688), which was given by Mrs. Mary Adeane; a large flagon of 1757 given by Samuel Horne 'for the more decent celebration of the Holy Communion' and an Elizabethan ciborium given in 1955. 

The registers for baptisms, burials, and marriages date from 1634. 

The churchyard is well stocked with trees, both limes and yews. It was extended in 1867 and a wall was built on the eastern side with money from bequests. There is a memorial to Thomas Toovey of Howe (d. 1720), and a tomb to the Revd. Thomas Williams (d. 1801). A lych-gate was erected in 1901 by the parishioners in memory of the glorious reign of Queen Victoria (1837–1901).

Historical information about St. Leonard's Church is provided by 'Parishes: Watlington', in A History of the County of Oxford: Volume 8, Lewknor and Pyrton Hundreds, ed. Mary D Lobel (London, 1964), pp. 210-252. British History Online http://www.british-history.ac.uk/vch/oxon/vol8/pp210-252 [accessed 30 March 2023].

St. Leonard's Church is a Grade II listed building. For more information about the listing see CHURCH OF ST LEONARD, Watlington - 1059424 | Historic England.

For more information about St. Leonard's Church see Parishes: Watlington | British History Online (british-history.ac.uk).