By the 14th century there was a road from Hendon up Bittacy Hill and continuing through Highwood Hill, known then and now as The Ridgeway. The roads weren't very good and it was not uncommon for travellers to use the side of the roads as the centres became muddy.
By the 16th century the roads were often very wide. As road transport improved through the 17th and into the 19th century, the side paths became wastes, which were sold off by the manor of Hendon. Many of the older buildings in Mill Hill Village were built on these wastes. The inhabitants of these houses were mostly well-off merchants and traders who required a home in the country which was close to their business interests in London. A number of these houses, such as Belmont and Littleberries, still remain.
The Ridgeway became increasingly important as an alternative to the Edgware Road as a means of travelling north out of London. A number of inns and public houses were opened to serve travellers. Many, like the Kings Head and the Angel, have now disappeared. At the end of the 18th century, Mill Hill had many more inns than was usual in a settlement of its size. By the 1820s Mill Hill's population had risen significantly around what is now the High Street and there were even a handful of shops.
In 1807 Mill Hill School was established for the children of non-conformists at Ridgeway House, formerly the home of the Nicolls, an important local family. The school was the first of a number of large institutions, such as schools and convents, to exploit the large houses.
There has been a number of famous and important residents of Mill Hill Village. These include the abolitionist William Wilberforce at Highwood Hill, and his friend Stamford Raffles (the founder of Singapore in the 1820s) at Hendon Park. Peter Collinson, the botanist, lived at Ridgeway House until his death in 1767, and James Murray, one of the compilers of the New English Dictionary, lived at Sunnyside on Hammers Lane.