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As the feudal system broke down in favour of a more commercial economy,  enterprising manor holders applied to the monarch for the right to hold markets and fairs. Ermine Street had deteriorated and the main route north from London went through the Lea valley.  Hoddesdon was in a position to benefit from a market and its charter dated from 1253. The manors in and around Hoddesdon changed hands through the years, and many of the smaller ones amalgamated or were taken over. By the 15th century, the major landowner was John Say, who obtained confirmation of the market rights.
 
Elizabethan Hoddesdon saw a continuation in growth.  The town’s position on a major road led to the building of many inns to cater for travellers. Some of these still stand. The Golden Lion, the White Swan and the Salisbury date from the 16th century, and the Bell became an inn in the 17th century. William Cecil, Elizabeth’s Secretary of State, became a major landowner.  The market was in its heyday, and for a few years the town had its own grammar school, financed from market tolls.
   
In the 17th century Marmaduke Rawdon, a wealthy merchant, built Rawdon House.  He put money into the building of the New River; he gave the town its fresh water supply, flowing from the urn of a statue known as the Samaritan Woman; and he assisted in the construction of a Market House.  Rawdon’s son, also Marmaduke, built the Grange. The Rawdons sided with the king in the Civil War and their fortunes suffered considerably.

St. Katherine’s Chapel was damaged during the Civil War, and was closed for services a few years later. A clock was installed in the early 18th century, and the building remained until it was demolished in 1835 and replaced by a new Clock House.

A small brewery, started about 1700, prospered under the ownership of the Christie family to become a major employer in the town in the 19th and early 20th centuries. The population of the town grew rapidly, and Hoddesdon parish was created in 1856 from parts of the existing Broxbourne and Great Amwell parishes.  The basis of the parish church was a private chapel built in 1732 in Amwell Street by an early brewery owner. This has been extended and altered over the years to become the present St. Catherine and St. Paul’s Church.

The Samaritan Woman
   
The Market House stood opposite the Bull,
whose sign crossed the road and rested on it
Movements to provide education for poor children gathered momentum in the early 19th century.  In Hoddesdon Mrs Easter Jones built a girls’ school in 1818, which was later relocated to National (Church of England) School premises in Pauls Lane, where a boys’ school had been built in 1844.  The first British (Non-Conformist) School was built in Esdaile Lane in 1841 by John Warner, a Quaker.  Warner, a London foundry owner, built himself a house called Woodlands in Hoddesdon, and spent much of his later life in the town.  Members of the Warner family lived at Lowewood until 1935.  The building is now the Borough of Broxbourne Museum.  The restored Samaritan Woman statue stands in its garden.