The Edgware Road was one of the first roads to be constructed by the Romans in.
The High Street may have had houses by the middle part of the 15th century, and the road functioned not only as a thoroughfare, but also as a boundary between the parishes of Little Stanmore (on the western side) and Edgware (on the eastern side).
There was a bridge over Edgware Brook by 1597, by which time the road was called Edgware Highway, and houses lined the road between the bridge and what is now Station Road.
On the eastern side of the road there was an inn called The George.
- 1454: estimated building date. Like many of the inns in Edgware The George serves travellers on the main road, but it also functions as the manorial court
- 1760: a fair in the back yard of The George and the adjoining field is held in May, for buying and selling horses and cattle, but by the 1790s it peters out
- 1810: the fair is moved further south to a field called Baker’s Croft, which subsequently becomes known as fair field (where Garret Road, Heming Road, and Elmer Gardens are today). The fair is held in the first week in August and is mostly for fun. There are 'rustic competitions', such as sack races, 'wheeling barrows blindfold', and pulling faces 'through a horse collar'
- 1834-1855: the fair also includes horse racing
- 1904: last fair is held because the tenants of the field no longer want a fair on their land
The Boot and Spur
Further up the High Street was the Boot and Spur (1753), later known simply as the Boot.
- 1767: Edgware has its own lock up, or cage, for confining prisoners to be tried at the court
- 1820s: the Edgware cage is situated close to the Boot Inn
- late 19th century: Charlotte Monk makes her living by selling water around the village taken from a well in front of the Boot
- the Boot survived until 1965.
The High Street
The High Street was first widened to accommodate the tramlines laid in 1904, demolishing a number of houses which later became The Forum, a parade of shops built in 1930 on the corner of High Street and Station Road by Charles Wright, a local manufacturer.
- further up, a row of shops were built around the same time, including 110 High Street (The Granaries) dated 1904
- the street was widened again between July and October 1931, and nearly all the older buildings were demolished (including the Old George Inn)