Traders and Craftsmen of Watlington were encouraged by the Grant of a Wednesday Market in 1252 to Richard, Earl of Cornwall, and of a Saturday Market and yearly Fair in 1302 to Roger Bigod. No attempt, however, seems to have been made to Free Townsmen from Villein Dues and they continued to pay Tallage to the Earl. The Tolls of the Fairs and Markets Descended with the Principal Manor until the 17th century, but by the early part of the Century they were being Leased to the Townsmen themselves. The Market was still being held on Saturdays and there were 2 Annual Fairs. The original Grant was for a Fair on the Eve, Feast, and Morrow of St Bartholomew’s Day (24th Aug), but by 1718 there were said to be 3 Fairs, on Lady Day (25th Mar), St Bartholomew’s, and on the Saturday before Michaelmas (29thSept), when Servants were hired. In the early 19th century there were 2 Fairs for hiring Servants, one on the Saturday before and the other on the Saturday after ‘Old’ Michaelmas (10/11th Oct). In 1852 Cattle Fairs were held on 5th April and the Saturday before 10 October; in 1939 there were still 2 Statutes of ‘Pleasure’ Fairs held on the Saturdays before and after ‘Old’ Michaelmas.
Compared with the Markets of Henley, High Wycombe, or Thame, Watlington’s Market was unimportant. In the 16th century Camden commented on its smallness, and at the end of the 17th century, it was so severely affected by outbreaks of Smallpox and Fever that it lost most of its old Trade to Henley. Although Smallpox had almost entirely disappeared by 1742, when Thomas Stonor sold the Tolls in about 1747 these were worth no more than around £100. Lack of Goods Communications more than anything else probably prevented Watlington from keeping up with its rivals, particularly after the development of new Routes to London through Stokenchurch and Henley. In 1822 the Roads round Watlington were described as ‘probably the worst in the Country‘, and this had already led to the loss to High Wycombe of much of the Produce of the Corn Belt below the Chilterns that was destined for the London Market. Another factor contributing to Watlington’s stagnation was that the nearest Navigable Water was 6 miles away. In 1822 this was said to be ‘a circumstance fatally adverse to the Prosperity of the place‘. In 1852 the Market, still mainly for Corn, was ‘thinly attended‘ and Thame Market took most of the Cattle Sales. The Market ceased to be held soon after.
Watlington flourished mainly as a Local Centre and Victuallers and Millers appear early in its records. 15th-century Court Rolls records the selling of Beer and Bread over the controlled Price, Millers were fined for taking excessive Tolls, and Butchers and Innkeepers for excessive charges. The records of the Stonor Family show that the local Gentry both bought from and sold to Watlington Craftsmen and Merchants. Mistress Stonor bought Broadcloth and ‘fine cloth‘ and Kersey in 1468 from a Watlington Weaver, in 1479 Elizabeth Stonor paid Watlington men 1s 8d for 5-days’ work in making Candles; in 1482 Wood was sold to a Watlington Trader; and in the 16th century Sir Adrian Fortescue’s Accounts record the purchase of Bread and Ale from Watlington. Sheep Farming on the Chilterns encouraged Wool Merchants and Weavers. In 1478 Robert Warner, Woolman, and at one time Bailiff of Watlington, was in debt to Thomas Stonor and was accused of being ‘an untrew man of his promesse‘. Warner sold his Wool in London and in 1476 negotiated for the Sale of 25 sacks of ‘young Cotswold‘ wool, 50 fleeces of fine wool, and 200lb of wool for £140. Connections with London Merchants were not unusual in the Middle Ages: in 1443, for example, William Torrynton, Chapman of Watlington, was summoned to answer for a 40s Debt to a London Girdler; and in 1453 a Watlington Husbandman was in Debt to a Salisbury and a London Merchant. The Town even attracted Settlers from the Netherlands. Simon Antony, born in Fleremere in Luke, who was living at Watlington in 1436, was presumably a Weaver or a Woolman.
Trades and Crafts recorded in the 17th, 18th, and 19th centuries show that Watlington supplied most local needs. There are 13 surviving Trade Tokens of the late 17th century, and among the people who purchased the Manorial Rights in 1669 were 4 Cordwainers, 3 Maltsters, 2 Fellmongers (hides & skins), 2 Carpenters, a Collar Maker, Mason, Shoemaker, and Tanner. The Nashes, prominent Parishioners in the 17th century, were Tanners and the Gregorys and Reveses were Weavers. Fell-mongers were recorded up to the early 19th century, An Apothecary was recorded in 1670, a Chirurgeon (surgeon) and Barber in 1679, Scribeners (writers) in 1674 and 1766, and two Lawyers occur in 1718. Glovers and Drapers were evidently prosperous, since Thomas Ovey, member of a wealthy Yeoman Family, was a Glover in 1615, and the successful Home family was mainly engaged in the Drapery Trade. Mr Edward Home was a leading Draper in 1688, and Edward Home with John Sibley supplied the clothes for Robert Parslowe’s Charity in the 1730s. In the 1740s Edward Horne was described as a gentleman. A relative, Samuel Horne, who became lord of Watcombe manor was a London Merchant in 1747. The Tooveys, Owners of considerable Property in the area, were also connected with the Drapery Trade.
Innkeeping was another profitable Trade, recorded in Waltington from the 15th century. In the 17th century Thomas Greendowne, Innkeeper of the ‘King’s Head‘, had Tokens bearing a Sugar Loaf and a Vintner’s Bush. At the end of the 18th century there were 6 Inns in Watlington, which came into the hands of the Local Brewers, the Haywards, by the early 19th century. These were the ‘Crown‘, the ‘Hare and Hounds‘, the ‘Red Lion‘, the ‘Three Crowns‘, the ‘White Hart‘, and ‘Black Lion‘. In 1823 there were also the ‘Barley Mow‘ and the ‘George‘ and about 1853 there were at least another 11 Beer Retailers in Watlington besides 2 in Greenfield, probably at Christmas Common (Fox & Hounds) and on Howe Hill (Jolly Poughman). In the late 19th century George Wilkinson, a Methodist, bought 6 of the Inns and Beerhouses and was able to close them. There were still 9 Beer Retailers in the Parish in 1903 and 7 Inns, but by 1939 there were only 3 Public Houses and 2 Hotels: the ‘Hare & Hounds‘ and the ‘Fox & Hounds‘.
Trading was encouraged in the 19th century by a local Bank, Blackall & Cozens, Established in 1810. William Cozens, a son of Thomas Cozens of Tetsworth, married Ann Blackall of Pyrton, and the Bank was Advertised as Blackall & Cozens in 1812, and in the same year Cozens was given Licence to issue Notes. The Bank flourished under the names of Thomas & William Cozens from 1815 to 1841. William Cozens died in 1844, and his successors at Watlington were Lydall & Co., in Shirburn Street.
The 1851 Census gives the 1st full description of Occupations and Trades in Watlington. There were about 200 Agricultural Labourers, besides Shopkeepers, Butchers, and Victuallers. Specialised Agricultural Crafts still flourished and 2 Sadlers, a Builder and Wheelwright, a Millwright, Cooper, Thatcher, and 3 Blacksmiths were listed, as well as an Iron-founder and a Tinman and Brazier. The Chief Industry was Shoemaking, described in 1844 as ‘a rather considerable Trade lately sprung up‘: in 1851 there were 5 Master Shoe & Boot-makers, employing a number of Journeymen; in 1852 there were 10 Independent Shoemakers and soon after there was another employing 49 men. In the later part of the Century this Trade declined because of competition from the Northamptonshire Shoe-factories. Lace-making was also a considerable home Industry in the 19th century. In 1762 and 1788 there was a professional Laceman or Lacebuyer in the Town and in 1851 a visiting Lace Dealer was included in the Census. In the early 19th century Lace was taught in a Special School for 40 or 50 Pupils. This Industry again was killed by Factory competition.
No other Industry has established itself in Watlington on any large scale, and in 1960 most of the Workers on the new Housing Estates worked in Oxford in Industry or Business. Opportunities for work in Oxford probably account for the rise in Population, which has taken place since 1921. During the 19th century the number of Inhabitants had increased from 1,276 to 1,943 persons by 1871, but had then fallen to 1,386 by 1921 because of the Agricultural Depression and the decline of Home Industries. Despite the loss of 278 acres to Pishill the downward trend had been checked by 1931 and by 1951 numbers reached 1,589.