The town continued to develop separately on the old Akeman Street  0.4 miles (0.6 km) to the south of the castle and to the west of St Peter's Church; with a triangle formed by Mill Street, Castle Street and Back Lane pointing towards the castle.
In 1156, Henry II officially recognised Berkhamsted as a town in a royal charter, which confirmed the laws and customs enjoyed under Edward the Confessor, William I and Henry I, and freed the town's merchants from all tolls and dues.
The charter also stated that no market could be set up within 7 miles (11 km) of the town.

The town became a trading centre on an important trade route in the 12th and 13th centuries, and received more royal charters.
In 1216, Henry III relieved the men and merchants of the town from all tolls and taxes everywhere in England, and the English Plantagenet possessions in France, Normandy, Aquitaine and Anjou.
The growing wool trade brought prosperity to Berkhamsted from the 12th century until the early Tudor period.
Four wealthy Berkhamsted wool merchants were amongst a group in Bruges to whom Edward III wrote in 1332, and Berkhamsted merchants sold cloth to the royal court.

In 1217, Henry III recognised by royal charter the town's oldest institution, Berkhamsted's pre-existing market.
Trades within medieval Berkhamsted were extensive: early in the 13th century the town had a merchant, two painters, a goldsmith, a forester, two farriers, two tailors, a brewer of mead, a blacksmith, carpenters, wood turners, tool makers, a manufacturer of roofing tiles and wine producers.
In the mid–13th century, a banker, the wealthy Abraham of Berkhamsted, financier to the Earl of Cornwall, lived in the town; this was unusual for a small town in a time of heightened persecution of Jews.

A 1290 taxation list mentions a brewer, a lead burner, a carpenter, leather workers, a fuller, a turner, a butcher, a fishmonger, a barber, an archer, a tailor, a cloth-napper, a miller, a cook, a seller of salt and a huntsman.
At this time, larger houses of merchants and castle officials appeared on the south side of the high street (including 173 High Street, the oldest known extant jettied building in England).
In 1307 Berkhamsted was a large town by English medieval standards with an estimated population of 2,000 to 2,500.
In 1355, there were five butchers, two bakers, nine brewers, two cobblers, a pelter, a tanner, five cloth dyers, six wheelwrights, three smiths, six grain merchants, a skinner and a baker/butcher.
In the 14th century, Berkhamsted (recorded as "Berchamstede") was considered to be one of the "best" market towns in the country.
In a survey of 1357, Richard Clay was found to own a butcher's shop twelve feet (four metres) wide, William Herewood had two shops, and there were four other shops eight feet (two metres) in length.
In 1440, there is a reference to lime kilns.

The town benefited when Edmund, 2nd Earl of Cornwall founded Ashridge Priory in 1283, two miles (three kilometres) away and within the castle's park.
At the foundation of the abbey, the Earl donated a phial claimed to contain Christ's blood.
Pilgrims from all over Europe passed through the town to see the holy relic.
The abbey grew quite wealthy as a result.
Edward I held parliament at the abbey in 1290 and spent Christmas there.
Berkhamsted burgesses sent two members to parliament in 1320, 1338 and 1341, but the town was not represented again.
In the mid-14th century, the Black Prince took advantage of the Black Death to extend the castle's park by 65 acres (26 ha), eventually producing a park covering 991 acres (401 ha).
In the 15th century, the town was reaffirmed as a borough by a royal charter granted by Edward IV (1442–1483), which decreed that no other market town was to be set up within 11 miles (18 km).
The town continued to develop separately on the old Akeman Street  0.4 miles (0.6 km) to the south of the castle and to the west of St Peter's Church; with a triangle formed by Mill Street, Castle Street and Back Lane pointing towards the castle. In 1156, Henry II officially recognised Berkhamsted as a town in a royal charter, which confirmed the laws and customs enjoyed under Edward the Confessor, William I and Henry I, and freed the town's merchants from all tolls and dues. The charter also stated that no market could be set up within 7 miles (11 km) of the town.
The town became a trading centre on an important trade route in the 12th and 13th centuries, and received more royal charters. In 1216, Henry III relieved the men and merchants of the town from all tolls and taxes everywhere in England, and the English Plantagenet possessions in France, Normandy, Aquitaine and Anjou. The growing wool trade brought prosperity to Berkhamsted from the 12th century until the early Tudor period. Four wealthy Berkhamsted wool merchants were amongst a group in Bruges to whom Edward III wrote in 1332, and Berkhamsted merchants sold cloth to the royal court.
In 1217, Henry III recognised by royal charter the town's oldest institution, Berkhamsted's pre-existing market. Trades within medieval Berkhamsted were extensive: early in the 13th century the town had a merchant, two painters, a goldsmith, a forester, two farriers, two tailors, a brewer of mead, a blacksmith, carpenters, wood turners, tool makers, a manufacturer of roofing tiles and wine producers. In the mid–13th century, a banker, the wealthy Abraham of Berkhamsted, financier to the Earl of Cornwall, lived in the town; this was unusual for a small town in a time of heightened persecution of Jews.
A 1290 taxation list mentions a brewer, a lead burner, a carpenter, leather workers, a fuller, a turner, a butcher, a fishmonger, a barber, an archer, a tailor, a cloth-napper, a miller, a cook, a seller of salt and a huntsman. At this time, larger houses of merchants and castle officials appeared on the south side of the high street (including 173 High Street, the oldest known extant jettied building in England). In 1307 Berkhamsted was a large town by English medieval standards with an estimated population of 2,000 to 2,500. In 1355, there were five butchers, two bakers, nine brewers, two cobblers, a pelter, a tanner, five cloth dyers, six wheelwrights, three smiths, six grain merchants, a skinner and a baker/butcher. In the 14th century, Berkhamsted (recorded as "Berchamstede") was considered to be one of the "best" market towns in the country. In a survey of 1357, Richard Clay was found to own a butcher's shop twelve feet (four metres) wide, William Herewood had two shops, and there were four other shops eight feet (two metres) in length. In 1440, there is a reference to lime kilns.
The town benefited when Edmund, 2nd Earl of Cornwall founded Ashridge Priory in 1283, two miles (three kilometres) away and within the castle's park. At the foundation of the abbey, the Earl donated a phial claimed to contain Christ's blood. Pilgrims from all over Europe passed through the town to see the holy relic. The abbey grew quite wealthy as a result. Edward I held parliament at the abbey in 1290 and spent Christmas there. Berkhamsted burgesses sent two members to parliament in 1320, 1338 and 1341, but the town was not represented again. In the mid-14th century, the Black Prince took advantage of the Black Death to extend the castle's park by 65 acres (26 ha), eventually producing a park covering 991 acres (401 ha). In the 15th century, the town was reaffirmed as a borough by a royal charter granted by Edward IV (1442–1483), which decreed that no other market town was to be set up within 11 miles (18 km).
Berkhamsted