The earliest known mention of the High Street is in 1334 when property with houses thereon was conveyed to John Page, the younger, and Helen, his wife, of Gravesend. This was in the parish of Milton and was stated to be 'abutting upon High Street towards the west'. The High Street of that time was not a continuous line of houses as we see it today. Between what is now the site of the old Town Hall and the river there appears, according to a document of 1456, to have been only two houses on the Milton side of the street until the riverside was reached, with one or two tenements on the Town Quay. It is probable that a channel ran down the middle of the street and that down its course went the unwanted domestic rubbish, washed by rains or periodical swillings with well water. The Town's Second Charter of Incorporation, dated 1568, required every inhabitant 'to weekly cleanse before his door for the avoidance of evil odours' under a penalty of three shillings and fourpence.

Between the Kent public house and the junction with Royal Pier Road was a parcel of land belonging to the Abbot of the Monastery of St. Mary Le Graces, Tower Hill, London. This was also part of the old manor of Parrock. The piece between the Kent and Bank Street was, in the early part of the 15th century, the site of Dame Anne's Hall. The other piece between Bank Street and Joe Coral's turf accountants was called Beelings (or Baldwin's Acre and the rest of the land on the north was called Stonehawe or Stonehall.

William Bourne (c.1535 1581), innkeeper, mathematician, gunner and mercer, well known for his writings on ordnance, inventions and navigation, owned messuages, tenements and gardens on the east side of the High Street.

By the late 18th century the street must have begun to assume something of the appearance it still had in the late 19th century, as Pocock, Gravesend's first historian writes: 'almost every tradesman had a sign and in the night when the wind blew strong, a concert of squeaking music filled your ears with sounds not the most pleasant'.

The demolition in 1928 of the New Prince of Orange (built in 1805 when the New Road was cut) which occupied the site of Burton's, the tailors, and of Bryant and Rackstraws, at one time the leading drapery and haberdashery store in the town, on the opposite corner (now Woolworths) in 1957 has completely altered the appearance of this corner. The High Street has doubled in width, as it was previously eight feet wide.

In 1963, the shoe shop at 43 High Street was demolished, and the late E.W. Tilley of the Gravesend Historical Society excavated the site from which it was apparent that a shoe shop had existed on the site for 150 years. From the contents of various rubbish pits, however, there was evidence that the site had been occupied continuously since the 13th century with slight slackening off in the 14th and 15th centuries, with extensive occupation beginning again in the 17th century.

Until Jury Street was cut in 1846 7 there was no outlet from the High Street other than pedestrian footways. A fire that occurred in the earlier year destroyed much of the property in the street and provided the opportunity to cut through into Princes Street. The name of the street commemorates the fact that a jury sat to assess the amount of damage and the cost of the change made.

To the north of Jury Street was The Catherine Wheel, which bore on its front the year of its erection, 1686. Half of this building remains and is now 56 High Street. The date stone is now in the local collection. The right hand pilaster of the former entablature can still be seen above the shop front.

The Common Market that the Charter required the Corporation to hold once a week was established between the new building and what is now known as Queen Street. At first an open space, in 1818 it was converted into two covered ways with stone columns supporting the roof, but with an uncovered centre area. The architect for this work was Charles Fowler, who was also responsible for Covent Garden and Hungerford Markets. The fish market was added on the site of the Shambles in 1829. This remained until the present market hall was built in 1897, when the columns were removed to the grounds of Milton Hall (see G M Arnold). The architect for the covered market was Edward J. Bennett and the builders Multon and Wallis. The mayor, John Russell, opened it on 18 December 1898.

Lower down the street on the east side is Bank Street, cut through in 1850 following another extensive fire, and so named from the bank that stood on its southern corner. Two early (1824) private banks were Messrs Brenchley Becket and Ride and Messrs Miller Twiss and Co. In 1823, Gravesend Vestry sustained a loss of £68 2s 11d on the failure of Messrs Hills and Sons.

Websites of interest: - Gravesend Market