Between the 17th and 19th centuries, Slough was an important staging post on the Bath Road. The two most dangerous places on the Bath Road - Hounslow Heath and Maidenhead Thicket - were either side of Slough, and rather than risk crossing them in the dark, many travellers preferred to stop here overnight.

Highwaymen were common in this period, particularly in the late 1600s and early 1700s, and anyone travelling by horse or coach was a potential victim. Mail coaches were also a target, and because of this threat people were advised to cut banknotes in half, and send the two halves separately. The Bath Road was particularly vulnerable, because as well as people travelling between London and the West of England, nobility travelling to and from Windsor Castle also used the road.

There are several local legends regarding the most famous highwayman of all, Dick Turpin. He is said to have drunk in the 'Crooked Billet' at Black Park and the 'Black Boy' in Slough. The ghost of a tollkeeper shot by Turpin is said to haunt the site of the old Toll House in Colnbrook. However, as Turpin operated mainly in his native county of Essex, there may not be any truth behind these stories.

There were several highwaymen who certainly did have a connection with Slough, due mainly to the proximity of Maidenhead Thicket. Among the highwaymen who operated there were 'Captain' James Hind and Claude Duval. (To read more about Duval, look at the article 'Claude Duval - gentleman highwayman' under 'Famous Slough'.)

John Hawkins and George Simpson belonged to a gang which specialised in robbing mail coaches. They operated throughout England, on one occasion holding up the Bristol Mail at Colnbrook. Hawkins was hanged in 1722 after being betrayed by his companions.

A highwayman that operated in the Salt Hill area for many years was 'Flying Hawkes'. He was known as a master of disguise. In one famous tale he was in the Salt Hill area, disguised as a Quaker, when he overheard a traveller claim that no highwayman would ever get the better of him. He followed and robbed the traveller, warning him not to be so boastful in future. Unfortunately, he was captured later that night by the Bow Street Runners. One of the reasons behind the formation of the Salt Hill Society in 1783 was to protect locals from robbers and highwaymen.

There is a legend that Ledgers Road in Chalvey was named after a highwayman called Ledger, who was hanged there.

In the late 18th and early 19th centuries, highway robbery gradually died out. There were several factors involved - most notably the establishment of the banking system, which meant that less money was being carried, and the formation of the Bow Street Runners, a prototype police force.