Distance: 9.9 miles

Difficulty of the terrain: medium

Get the route: via Ordnance Survey Maps or download the GPX. file from Dropbox

Walk across the Warwickshire Cotswolds from Shipston-upon-Stour via Cherington and Whichford. Ends at Great Rollright in Oxfordshire famed for its proximity to the Rollright Stones.

The Story

Route Notes

Getting Back

Heart of the North Cotswolds

Situated just over the county boundary from Warwickshire, Great Rollright is one of the most northerly settlements in the Oxfordshire Cotswolds.

It is situated high up on the Cotswolds plateau more than 200 metres above sea level. In most regards it is a quintessential Cotswolds village, one which has grown up around its parish church since the Middle Ages, its oldest houses essentially farmsteads which have become absorbed into a minor urban settlement. 

The village’s lands were enclosed in 1776 when led to the consolidation of farming in a small number of large commercially orientated farms which decisively shaped the way the village has developed since. These days, like so many of its peers Great Rollright’s population is predominantly comprised of people who work elsewhere or who are retired.

Like many villages, Great Rollright’s parish church, which is dedicated to St. Andrew, stems from a myriad of different time periods and is in a mishmash of different styles. It is most noted amongst architectural historians for its unusually well preserved 12th Century porch. The bulk of the contemporary building’s presentation though, again like so many other old Anglican churches, is predominantly mid-Victorian in terms of decoration. Some of the church bells though, quite remarkably date back to the 1690s when they were cast in Northamptonshire by a bellmaker called William Bagley, who was based just over the county boundary in Northamptonshire. 

Perhaps the most remarkable thing about Great Rollright are the prehistoric megaliths collectively known as the Rollright Stones which lie a mile or so to the east, right on the boundary with Warwickshire and the Midlands. They are readily reachable along footpath’s from the village, a journey which takes no more than half an hour.

The Walk

Get the route: via Ordnance Survey Maps or download the GPX. file from Dropbox

I create the Walk Midlands routes via Ordnance Survey Maps Explorer enabling me to take them on my phone. Subscribe yourself via the banner above.

This walk to Hook Norton in Oxfordshire, crossing the Cotswolds escarpment, begins from Shipston-on-Stour in Warwickshire.

Having alighted the bus on the A3400 Shipston-on-Stour’s main road in the town centre, walk past the unusually named Anglican church called St. Edmund King and Martyr, with a rectangular tower that backs onto the street front.

Near the southern edge of the town centre turn down Mill Street, crossing the River Stour into open countryside.

Soon on the right there is a footpath running off into meadows beside the Stour. This path, like much of the route through Warwickshire towards Hook Norton, comprises part of the Shakespeare’s Way. One of the UK’s incredibly long, conceptually bonkers, long distance footpaths inspired by Early Modern history, in this case, allowing would be pilgrims to walk between Stratford-upon-Avon and The Globe Theatre in London or vice versa.

Follow the footpath along the course of the river into the little hamlet of Barcheston which like most settlements in this part of the country has a large, picturesquely situated church.

Beyond Barcheston pick up the path across meadows, the distant Cotswolds escarpment now visible in front of you, and approach the larger village of Willington.

You walk across some townlands and enter Willington, following the main road through the village.

On the far side after a short distance along a country road you pick up a footpath, heading steadily uphill across fields towards the Cotswolds escarpment.

Turn right and follow the road down towards the village of Cherrington which sits on the edge of the Cotswolds National Landscape. The road was quiet with only a few cars, cyclists and the occasional equestrian, when I walked the route on a Saturday morning. There is a footpath which would lead you from this point down to the village, but due to a bridge being completely out of action across the deep brook at the bottom of the wold, it is not currently possible to use it to reach the village.

Once on the edge of the Cherrington, walk uphill towards the church towards where the bulk of the houses lie.

Turn right to reach the old heart of the village, which is in a quintessential Cotswolds style, all yellow stone houses arrayed along a wide main street.

Before reaching the village centre turn left up a cul-de-sac and pick up a track leading out into the fields.

This peters out into a footpath which runs steadily uphill. There are great views back behind you across southern Warwickshire as you ascend the escarpment.

Upon reaching the very top now around two hundred metres above sea level you approach a stand of trees called Margaret’s Hill Coppice, which has a large holiday home, which presumably was a farmstead with commanding views long ago, in the middle of it.

Past the holiday homes you pick-up a driveway which runs across the hilltop plateau towards a main road.

Upon reaching the road, which was also quiet when I walked the route, turn right until you reach the entrance to Whichford Woods on the left. 

Enter the woods and follow a path downhill through a wold contained within the trees then follow it up the corresponding side of the valley.

At the top of the wold follow the path running left straight ahead through airy woodland.

Leave the woods through a gap in the trees and pick up a bridleway path running across the fields at the top of the plateau.

After some distance, having crossed several fields you reach a gateway out onto a lane.

Once on the lane turn right and follow the road uphill.

At the top of the hill you reach a crossroads near the top of the hill. This is where you cross the county boundary leaving the Midlands.
At this junction you walk head right, and taking care as traffic can be quite heavy and travel rather fast, follow the road which runs along the top of the plateau.

Presently you reach some woodland just after passing a small farm.

On the far side of the trees you reach the cross road on the northern edge of Great Rollright.

This is where the walk ends.

Getting Back

At the time of writing in summer 2025 Great Rollright was served by the 488 bus. This runs very frequently on Mondays through to Saturdays between Chipping Norton and Banbury. Chipping Norton has bus services across the Cotswolds, while Banbury has even more extensive bus services and a mainline railway station, serving destinations in the West Midlands and the South East. Bus services are less frequent on Sundays with only five services a day each way. The last one to Banbury departing at 16:48 and to Chipping Norton at 18:06.