THE IRON AGE fortifications of Woodbury Hill and its possible occupations during the Roman period have already been dealt with, but in later times a chapel known as the Anchoret's Chapel was built on Woodbury's flat top near the western edge. The date of the foundation of this chapel is not known, but it is known to have existed in the 15th century when it is referred to in Dean Chandler's register of visitations, in which John Sperhauk is quoted as chaplain of Woodbury in 1408, and John Hyde in 1411.
Little more is known of the chapel except that its foundations were still visible in about 1770. In association with the chapel was a very deep well, necessarily so on Woodbury Hill, known as the Anchorets Well, in which, according to tradition, a golden table or tablet had once been hidden. The well was also reputed to have produced water having remarkable healing properties (perhaps due to the tablet?) and for this reason large numbers of people made annual pilgrimages to the well on 21 September, the date of its dedication, to drink the water.
These annual gatherings were probably responsible for the origin of the fair, as it was always held during the week in which 21 September fell, and it seems likely that such large gatherings would have attracted prospective salesmen and entertainers. There is a tradition that the fair originated through a traveling trader in cloth, who having been drenched by a heavy storm, stopped on Woodbury Hill to spread and dry his soaked cloth.
Passers by, seeing the cloth laid out in this way assumed it was for sale, and in a short while the trader had disposed of his stock with little effort. He returned again the following year with the same result and repeated it annually when other traders began to follow his example until the trade grew to sufficient proportions to rank as a fair and warrant a charter. This traditional story seems likely enough when considered in the light of the annual pilgrimages to the well. The trader's first visit probably coincided by chance with the large gathering at the well on 21 September, as he would be unlikely to have met many prospective purchasers on any other day of the year, and it would also account for his returning in a year's time presumably on the same date.
Whatever the origin of the fair may have been it certainly developed into the largest in the south of England, and on what must have been one of the most unusual and dramatic of fair sites-the flat top of an Iron Age hill fort about 350 feet (105 metres) above sea level, and some 13 acres (5 hectares) in extent. The fair probably originated well before the year 1200, but charters for it are known to have been granted by Henry III in 1231, 1235 and 1266 and confirmed by King Edward II in 1325. The fair began to decline during the 18th century, as the tolls which had formerly amounted to over £100 each year had decreased to £30 or £40 by 1730. In later times the trading side of the fair had almost disappeared until in 1938, after more than 700 years, it had become a two day fair of entertainments only. After being discontinued during the 1939-45 war it was revived for a few years until 1951 but has not been held since.
The fair used to last for five days from September 18-22, and each day was set aside for a particular purpose as follows:
1. Wholesale Day. As its name implies, mainly for the benefit of wholesale traders. On the remaining days retail trade was carried on.
2. Gentlefolk's Day. Devoted largely to entertainments. On this day oysters were traditionally eaten, and even today oyster shells may be found under the turf on the hill.
3. Allfolks Day. A day of general dealing and entertainments with popular appeal.
4. Sheep fair Day. Particularly for dealing in sheep, cattle, horses and other livestock.
5. Pack and Penny Day, when all the unsold goods remaining were offered at reduced prices.
The first roast pork of the season was always obtainable at the fair, and several local inhabitants took out special licences to sell liquor for this one week of the year, in addition to that obtainable from the permanent public house on the hill.
Although cheese, hops, cloth, cattle, sheep and horses were among the main commodities dealt in at the fair, almost anything else could be bought or sold there. As an example of the variety of merchandise available, there is an item concerning Woodbury in the accounts of Corfe Castle for the year 1282. In this year, during the Festival of the Nativity of the Virgin Mary (the week in which the fair was held) news came that the King was expected to visit Corfe at short notice, so that building repair and alteration works then in progress were hurriedly finished, any materials still required being purchased locally as far as was possible. Various items of ironmongery were obtained at Woodbury Hill fair in connection with this work, including great iron spike nails, locks and keys. Four great locks with keys cost 4s.
In its heyday the fair attracted thousands of visitors each day and traders came from as far a field as Birmingham, Norwich, Exeter, Bristol and London, as well as from most of Dorset and neighbouring counties. Visitors flocked to the fair from all the surrounding towns and villages, whether to conduct serious business or simply for pleasure, and most farm workers in the locality were given a day off to attend-about the only day's holiday they had during the whole year. Dorchester was said to have been practically deserted during the week of the fair, and the effect on Bere Regis must have been rather the reverse. For days before the fair the roads and lanes around the village were thronged with people, goods and animals, particularly sheep, being driven to the fair, and the whole period was quaintly referred to as Woodburytyde in the old churchwardens account book of 1682-1740.
By the end of the 19th century the fair had declined considerably from its former importance, but was still a thriving two day event of principally entertainments. From the old parish magazines we find that when the two fair days adjoined or occurred on either side of Sunday, as they did in 1895, an open air Service was normally held on the hill on the Sunday afternoon. The Church Itinerant Mission usually seems to have attended the fair each year, when a tent was provided as a schoolroom so that lessons could be given to the children of the stall proprietors and others, and over 40 of such children attended this improvised schoolroom in 1895.
In the 18th century there were a number of permanent buildings on the hill used each year in connection with the fail, arranged mainly on either side of the central concourse. These buildings probably formed the basis for some of the cottages later built on the site, as some of these fair buildings were, in 1788, used as temporary accommodation for families made homeless by the disastrous village fire in June of that year, and no doubt the temporary accommodation became permanent in a number of cases.