The Old and New Roads from Oxford to London
It is hard to imagine now, but the present main road through Headington did not exist until the end of the eighteenth century. Jeffries' map of 1769 (below) shows St Clement’s in the bottom left-hand corner. The first turning on the left is Marston Road, and then on the right (marked in bold as a highway) Cheney Lane leads seamlessly into Old Road, then the turnpike route to London over Shotover. At the top of the hill the road curved round into Cuckoo Lane, and a fork is a fieldpath that roughly follows the course of the present Headington and London Roads.

Old London Road
Until 1789, coaches travelling from Oxford to London had to turn right half-way up Headington Hill into Cheney Lane, which led to the Old London Road. (The name "Cheney" is thought to refer to a chain that once formed a barrier across the road to ensure that carriages stopped to pay tolls.) There is a stone dated 1667 near the end of the lane which reads "Here endeth Oxford mile hy way", marking the end of the mile of road beyond the city gates which the corporation was bound to repair, and underlining the fact that this now quiet road was once the most important route in and out of Oxford.
Kings and queens would have passed along Cheney Lane, and they were usually escorted into Oxford from the foot of Shotover Hill. According to Anthony Wood (I:412) Shotover could be seen from the top of St Mary the Virgin tower. He records how on 7 September 1661 the senior members of the University gathered in St Mary’s Church to await the visit of the Earl of Clarendon (Lord Chancellor of England and Chancellor of the University) and “caused a man to goe up to the battlements of the steple and there to watch his coming over Shotover Hill”. This enabled the to process to Magdalen College, by which time the Chancellor’s coach, drawn by six Flanders mares, was "comming out of Cheyney lane".
The first public coach service between Oxford and London (via Old Road, Shotover, and Wheatley) started early in Charles II’s reign. At first the journey took two days, breaking overnight at High Wycombe or Berkhampstead; but from April 1669 the "Flying Coach" achieved the journey in one day, leaving the Mitre in Oxford at 6am and arriving in London at 7pm. It operated in summer only, departing from Oxford on Tuesday, Thursday, and Saturday and returning from London on Monday, Wednesday, and Friday. Anthony Wood describes a journey he took on the very first coach on Monday 26 April 1669:
Munday, was the first day that the flying-coach went from Oxon to London in one day. A.W. went in the same coach, having then a boot on each side. Among the six men that went Mr. Richard Holloway a counsellour of Oxon (afterwards a judge) was one. They then, according to the vicechancellour’s order stuck up in all public places, entred into the coach at the tavern dore against Alls. Coll. precisely at 6 of the clock in the morning, and at 7 at night they were all set downe in their inn in London.
In 1671, this was extended to a daily service, and an advertisement slip for that year reads:
To London Every Day
These are to give notice that every day in the week there will be a coach set out (at six aclock in the morning) from Thomas Moor’s house over against All-Souls Colledge in Oxford which shall commodiously perform the whole journey to London in one day, and from the Saracens Head on Snow-hill London to Oxford again the next day, and so constantly for this summer half-year.. If God permit
Accidents did happen: Jackson’s Oxford Journal reports how on Friday 18 June 1779 one of the night coaches turned over at the corner of Cheney Lane: one passenger was killed, one broke a leg, and three others were badly bruised.
Shotover Hill was too steep for horses to pull laden coaches, so passengers had to get out and walk. On 20 December 1689, Wood reports that Matthew Slade, a Dutch physician aged 63, died in the London stage coach between Shotover and Wheatley, his death "supposed to be occasion'd by his violent motion going up Shotover Hill on foot".


New London Road
In 1773 the Trustees of the Stokenchurch Turnpike resolved to apply to Parliament "for power to divert the Road, and entirely avoid Shotover Hill", and in 1788 sought
to impower the Trustees to compleat a Road from the Bottom of Cheney-Lane, upon Headington-Hill, to Forest-Hill..., to be used instead of the present Road up Cheney-Lane and Shotover-Hill.
In 1775 the natural hollow way of Headington Hill was cut out more deeply from Cheney Lane to the top, but progress was slow because of disputes over the exact route and a shortage funds. In 1788 the term and powers of the previous act were enlarged, and finally in 1789 the old route was abandoned and coaches took the new London Road, which followed the route of the present A40.
The part of the Stokenchurch turnpike that ran through Headington was provided with a toll-gate at the junction with Windmill Road, a coaching inn (the Britannia, originally known as the White House), and milestones at the top of Headington Hill, near Wharton Road, and at Thornhill Park & Ride.
As a result, after 1789 Old Road became a quiet backwater leading to Quarry and Shotover, and even after the University abolished the one-and-a-half mile residence limit for dons in 1915, its development was leisurely. Until very recently buses were not allowed to run along it because of the number of hospitals in the area.
In 1818 the Headington Vestry contracted for the repair of the Turnpike Road from St Clements to Wheatley Bridge, and offered the responsibility for maintaining the section from the "4-mile stone" (to the east of Sandhills) to Wheatley bridge to the Parish Officers of Wheatley for £110 a year.
In 1878 the Stokenchurch Road was deturnpiked, as traffic had dwindled because of the advent of the railways. In 1889 the Co-op purchased the old turnpike house on the south-east corner of the central Headington junction and demolished it, putting up the building now occupied by Buckell & Ballard. But it was not until the 1920s, when the three villages of Headington had grown to meet each other and needed a central shopping area, that the London Road was fully developed as a shopping centre.
J. M. W. Turner’s painting of a coach on Headington Hill in 1803

The above engraving dates from 1842 and appears to show the junction of Cheney Lane and Headington Hill. The Oxford students have come part of the way up the hill and are just turning right into Cheney Lane. Behind them are the spires of Oxford.
The students are being greeted by a man in a smock, presumably the driver of the Oxford & London fly (a one-horse hackney carriage) that stands beside him. By travelling to London by the old route over Shotover via Cheney Lane and Old Road, a fly could avoid the toll payments on the new London Road, and presumably could pick up passengers at Headington Quarry, the Windmill, and the Warneford Lunatic Asylum, which were now all off the beaten track.
In 1852 Mary Coppock is listed as a fly proprietor at the Black Horse in St Clement’s (to the east of the St Clement’s toll-gate), and on 24 June 1856 her fly is advertised as taking the route "via Headington windmill and Shotover" for a Grand Temperance and Peace Festival.