A small hamlet known to exist from at least 1294 was called Cricklewood by 1321. By the 1750s the Crown Inn (rebuilt in 1889) was providing refreshment for coach travellers. The first signs of Cricklewood becoming an area of town could be seen by the 1850s, with a number of substantial villas and houses along the Edgware Road such as Rockhall Lodge and Rockhall Terrace.
In 1868 the Midland Railway Company opened the station. In the summer of 1881 the Midland company moved its locomotive works from Kentish Town to the new Brent Sidings, and in October of the same year it was announced that new workers accommodation would be built, later called the Railway Terraces.
The street names, such as Gratton Terrace, are associated with the Midland Company.
A builder called Mr Finch laid out a handful of suburban roads directly behind the Crown Inn, including: Yew, Ash, and Elm Groves in 1880. In 1883 the London General Omnibus Company terminated services to Regents Street at the Crown, and in 1884 the station became the terminus for the Midland Railway's suburban services.
Cricklewood had become the edge of London. Building continued in the 1890s with houses and shops built along part of Cricklewood Lane. Along what had become Cricklewood Broadway, new shops replaced the earlier villas of the 1850s.
In 1904 trams ran from Cricklewood to Kilburn, and in 1909 to the recently opened Golders Green underground station. Edwardian streets including Thorverton, Caddington and Dersingham Road were laid out from 1907.
A number of factories were opened during the late Edwardian period. These include The Phoenix Telephone Company in 1911, the aircraft manufacturers Handley Page Ltd from 1912 until 1917 at 110 Cricklewood Lane, and Smith's Crisps.
The area was finally built over from 1929 to 1933. Cowhouse Farm, latterly Dickers Farm and finally Avenue Farm, was closed in 1932. From 1908 to 1935, Westcroft Farm was owned by the Home of Rest for Horses. At its peak it could house 250 horses.
The Metropolitan Borough of Hampstead opened the Westcroft Estate in 1935.