The market town of Hoddesdon lies in the northern part of the Borough, about 18 miles from central London on the old High Road. The area has been inhabited since medieval times, and although the early history of Hoddesdon is obscure, it appears that the town began life as a small off-shoot of nearby Broxbourne. Certainly by the 13th century Hoddesdon had become a centre of some importance in its own right, with a regular market.

A common feature in the medieval calendar of an English town was the fair, a large occasional market with a range of sideshows providing entertainments. Hoddesdon’s first fair was granted by King Henry III in 1253 on the Feast of St. Martin, and a second was granted by Queen Elizabeth I in 1559 to be held on the Feast of St. Peter, 29th June, and the following two days. 29th June became a town holiday up until the 19th century, by which time the fair, which was held in the High Street and sometimes at Pound Close, had become less a market and more a carnival.
Around 1631 Hoddesdon received its first public water supply. When Sir Marmaduke Rawdon built Rawdon House just south of the town he supplied it with water via a lead pipe from High Grounds now known as High Leigh. This provided more than enough water for household needs, so a new pipe was laid to the southern end of the High Street, where the statue of The Samaritan Woman was installed to distribute water to the townsfolk. The statue is now sited in the gardens beside the Borough Council’s Lowewood Museum.

As the 17th and 18th centuries progressed, Hoddesdon developed into an important coaching centre. Improved coachbuilding techniques and advances in road building led the period 1780-1830 to become the golden age of coach travel. At one stage Hoddesdon had over 30 coaching inns. By 1835 the largest three alone had stabling for over 1,000 horses. By 1840 the Northern and Eastern Railway reached Broxbourne and within a few years the coaching business collapsed.

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