In 1523 Totnes was the second richest town in Devon, and the sixteenth richest in England, ahead of Worcester, Gloucester and Lincoln.  In 1553, King Edward VI granted Totnes a charter allowing a former Benedictine priory building that had been founded in 1088 to be used as Totnes Guildhall and a school.
In 1624, the Guildhall was converted to be a magistrate's court.

The two main suburbs of Totnes- Little Totnes,  were located on a continuation of High Street beyond the West Gate, where the Rotherfold, the cattle market ,in an area that originally extended from where Leechwell Street leaves High Street to where the Lamb Inn is today.
The other suburb centered on  Follaton Manor owned by Totnes Prior which sat astride old Plymouth Road, the original line of the road leading  directly from the West Gate, although this was changed when the burgage plots of Little Totnes were laid out.
Its wealth came mainly from wool and the little town abounded with merchants - rich men on the way to making vast fortunes from raw wool at first and later  from wool cloth, straight whites, woven on looms set up upstairs rooms - rooms which still have triple windows in their frontage - which can be seen on the first floors of the buildings all along Butterwalk -
Merchants lived over the shop and there were Pomeroys amongst them -probably younger son of the Barons Pomeroy who until 1547 lived a mile or so away at Berry Pomeroy Castle -  younger son often had to make their own way -and being
close to a busy wealthy town like Totnes must have been not only exciting but useful!

The merchant class was a close knit one, interrelated by marriage, there were around a hundred merchants at any one time in the town through many generations. One in every twenty families was likely to be a merchant family. In Exeter there were names  such as Thomas Prestwood, who came from Worcester and John Bodley whose widow this gentleman married; Thomas Bodley grandson of John and Nicholas Ball of Totnes, one of the richest towns in England, a trader in pilchards. There was also Thomas Richardson a wine merchant who came from Leicestershire, a merchant adventurer and keeper of a wine tavern.
There were also humble men made wealthy by clever trading and shrewd investments, men who carried name such as Peryam, Midwinter, Blackall or Blackallers, Martins and Spicers all successful merchant in Exeter during the time of Elizabeth I. 1558-1601.

In Totnes there was John Gyles who became a Merchant Stapler and the richest man in Devon. A man who bought  an ancient property in the country not far from Totnes and either built a new house or enlarges the old one, Bowden House. There were men like Richard Pomeroy with his wife Alice whose mother  Agnes had married for a second time after his father Thomas's  death  and became wife of Edward Harrys,who may also have been merchants, they were certainly rich enough. 
Others names occur as signaturies to various documents, names such as Thomas Werthe, esq., William Floyer, esq., John Butayde, Henry Drake, George Faryngdon, Vincent Maynerd, John Werthe, Richard Sachefyld, John Trewman and John Bagtorr. John Carswell John Wolston of Staverton,  Nicholas Holeway and Humphrey Walrond John Crewes Phillip Horswill, John Doartes. These all may have been Totnes merchants in their time.

By the middle of the 16th century middlemen, dealers in wool emerged as a separate class. 
The broggers or fellmongers bought wool and wool fells or sheepskin, from small growers, selling all they bought. They might have become moderately wealthy, acting as a clothier as well. Many later abandoned this for the profitable activity of simply dealing in wool.

There were the Staple Merchants at the top, next came the commodity dealers such as leather workers and glove makers and lastly the Broggers who sold all the wool they bought. 
The Merchant Staplers generally would have owned at least two properties. A large country house in an area where wool was produced and a town house where they carried on their business.

The Glovers and the worker in leather traded in wool as a by-product of their craft. They purchased wool fells or sheepskins and before they could process the pelts, the fleece had to be removed. This done, they sold the wool to dealers and other manufacturers and since everyone wore gloves, glove makers were great dealers in wool.

The Merchant’s middleman, who travelled his area collecting the great bundles of wools, would usually have been prompt in collecting from the growers. If the purchase was very large he might buy in three instalments. These were at set times. The Feast of St Bartholomew, (August 24th), the Feast of All Saints (1st November) and the Feast of Purification (2nd February). Occasionally the clothier would leave the wool with the growers for a whole year, waiting for prices to rise. This caused sheep farmers to complain bitterly since it inhibited their money flow. Most of the time collection was immediate and the wool was carried to the clothiers warehouse.

Many wealthy dynasties were founded at that time,  Devon men like Raleigh, Drake and Hawkins who explored the globe  helping trade improve . There was the risingJohn Gyles with his newly enlarged property at Bowden.
Sir Walter Raleigh, that Devon born courtier, poet, explorer and for some time favourite of  Queen Elizabeth I, who used his position to gain  licenses to export  Totnes produced cloth, unfinished whites, something which was prohibited at the time.  He became very wealthy on the profits and may well have an effect on local trade in Devon.
Raleigh was also Warden of the Stanneries and  legend has it that he was arrested in 1618, on the Buckfast road near Ashburton, after leaving a favourite hostelry, the Exeter Inn in West Street  Ashburton. He was carted off to the Tower of London, later being ignominious deprived of his head.

The price of wool and the trade fluctuated through this period and various means were used to elevate the prices. 
In 1571 Parliament decreed that everyone over the age of six had to wear a hat on Sundays and on Holy days. The hats had to be made of English woollen cloth.  A hat was to become part of everyone’s ordinary costume as were gloves. It was only in the latter part of twentieth century that the wearing of a hat and gloves to go out ceased to be commonplace.

  In Totnes by the late 17th century, for reasons that are unclear, possibly lack of investment in the New Draperies , lack of imagination or possibly a complaisance about the continuation of their fortune, it not known  but by 1665 the wool trade in Totnes was no longer flourishing and the busy little town became a quieter place.