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Take a drive between from Oxford to Evesham on the A44

by Midlands Lifestyle
21 August 2025
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Take a drive between from Oxford to Evesham on the A44
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When Bradley W. asks contestants on ‘The Chase’ in his inimitable way, ‘so, if you was to win some money, what would you do with it?’ he’s sometimes treated to a response regarding Route 66 and a suitable mode of transport such as a Winnebago or Harley Davidson. This set me thinking about our very own Route 44, a.k.a. the A44, which is a major road connecting Oxford with Aberystwyth; although I’m only interested in the Cotswolds section I could easily journey on as far as Leominster in Herefordshire as my paternal grandparents held court there.

Effectively the start of the author’s journey along the A44, this is the exit off the A34 which leads to the A44, signposted for Evesham and Woodstock, but also for the Peartree services where the author once stayed. The A40 is also signed here as Firstly, a bit of history. The A44 road was opened or designated in 1923 between Chipping Norton and Aberystwyth. After WW2 a section in Wales was renumbered as the A470 but that needn’t concern us here, however, there was another change to the A44 in the 1970s when it was extended on to Oxford (our start point for this jolly), taking part of the A34 at the time when the M40 was completed. In terms of the history of the road, that’s pretty much your lot although there’ll be plenty of history to pick up on as we make our way along ‘Route 44’.

I’ve actually trolleyed my way up the A34 from my south coast haunt and arrive at a big roundabout where I can pick up the A44 towards the Cotswolds as well as the A40 around Oxford. It’s quite a major junction so is blessed with the Welcome Break Peartree Services, or the ‘Oxford Services’ as I refer to them, which is a misnomer on my part as the real Oxford Services lie at Junction 8A on the M40. I did actually stay at the Peartree ones once when I fancied taking in an evening footie game at Oxford City FC which is only just down the road. Although Oxford is technically my start-point I’m not going to launch into hyperbole about ‘dreaming spires’ and such like as I’m getting no nearer the city than these services. It’s time to set off from this busy perch on the northern section of Oxford’s ring road.

The Turnpike Inn, which is on the A44 at the village of Yarnton. Photo: Motacilla/Creative CommonsThe Turnpike Inn, which is on the A44 at the village of Yarnton. Photo: Motacilla/Creative Commons We proceed north-west and there’s a two-mile section of dual-carriageway to excite the petrol-heads as we zip through Yarnton and Begbroke before sidling past Blenheim Palace and into Woodstock. It would be easy for me to go overboard at the Palace, very Churchillian indeed with Winston born here and the earlier Churchills (John and Sarah) building this place with the considerable help of architect-playwright Sir John Vanbrugh, but I prefer to sidle into the old country-town of Woodstock instead. It has royal connections to make other places exceedingly jealous. Henry I had a deer park and zoological collection here, whilst Henry II set up his mistress in the place (as you do), and the market owes its origin to nasty King John.

Passing through the historic town of Woodstock. Photo: John Miller/Adobe StockPassing through the historic town of Woodstock. Photo: John Miller/Adobe Stock The famed Black Prince, son and heir of Edward III, was born here (1331) and Princess Elizabeth (Elizabeth I) was also briefly under house arrest here during the reign of her elder sister, Mary I, and would later return here in state by which time Woodstock was one of the greatest glove-making centres in her realm. See what I mean? Returning to the matter of Winston Churchill, well, he climbed one of the old chimney pots in the town, a ‘soaring medieval construction’, when he was a naughty lad aged 12; good job he didn’t fall and break his neck. This is what’s so lovely about this country. We’ve only travelled five miles and we’ve gone from modern services to all this history, much of it royal. Dare I say that there are some countries, far bigger and more powerful than ours, who can’t offer as much and they know it.

Chipping Norton High Street. Photo: David Dixon/Creative CommonsChipping Norton High Street. Photo: David Dixon/Creative Commons We continue north-west through Enstone where there’s a post office on a green; I’ve been in there for ‘stuff’. Before you can say ‘we’ve got more history than you’, we’ve rocked up in Chipping Norton, smack in the main market street, the wide market place containing much good 16th- and 17th-century stonework. This is the highest Cotswold town in Oxfordshire, an old wool town still dominated by its wool church, the ‘Chipping’ bit denoting a market in Old English, and a place that was prosperous as early as the 13th century. The notable Market Hall was built in 1842; a gallant attempt to blend in with the town’s Cotswold ambience. On the way out of Chipping Norton we pass Bliss Mill, a Victorian pinnacled and turreted tweed mill which brought some much-needed employment to the town at a time when it was struggling. Built in 1872 for William Bliss, a cloth manufacturer, the mill would do well out of WW1 when it obtained a large khaki order for the British Army. The standout building was converted to apartments in the late-1980s. I must go though as I have another eight miles to chug to my next destination.

The post office at Neat Enstone, Oxfordshire, which the author passed on his way to Chipping Norton. Photo: Motacilla/Creative CommonsThe post office at Neat Enstone, Oxfordshire, which the author passed on his way to Chipping Norton. Photo: Motacilla/Creative Commons I feel like I’m in the Cotswolds now. There’s hills, bends and turns, single-carriageway, and not much opportunity to overtake which nevertheless impedes some drivers not a jot; it seems that having a vehicle in front of them is an affront. I chug unconcernedly from Oxfordshire into Gloucestershire and head for Moreton-in-Marsh which I understand to be a ‘prosperous-looking small town’. It has a spacious feel with its wide grass-verged main street but if you think you might find a marsh you’ll be disappointed; it’s actually a corruption of ‘march’ which means a boundary (as in the Welsh Marches). That broad eye-catcher of a street is actually built on the old Roman Fosse Way and was originally the crossroads of four counties, hence that ‘march’. Given the mention of Welsh Marches it’s kind of apt that there’s a church here unusually named St David’s, well, unusual for this part of the world at any rate.

The A44 approaching Fish Hill. The A44 bends round to the right before negotiating a number of tight bends on a steep descent of Fish Hill. The minor road to the left leads to Broadway Tower and Snowshill. Photo: Michael Dibb/Creative CommonsThe A44 approaching Fish Hill. The A44 bends round to the right before negotiating a number of tight bends on a steep descent of Fish Hill. The minor road to the left leads to Broadway Tower and Snowshill. Photo: Michael Dibb/Creative Commons Having effectively crossed the A429 which burrows down to the likes of Stow and Cirencester we do a bit of hill-climbing at the appositely-named Bourton-on-the-Hill. There’s plentiful woodland on this next stretch so there’s dappled sunlight and a pleasant drive with turnings to the likes of Blockley and Chipping Campden, both on the right, before we come to a turn on the left for the folly Broadway Tower and then the steep low-gear descent down Fish Hill with its sharp bends. I’ve always quite enjoyed the slalom up and down this semi-mountain although my modest petrol vehicles of the past really did struggle with the ascent; a little shout-out then for the EV (I have one now) which is untroubled by the climb.

Just after Bourton-on-the-Hill is the Quarry Service Station. Photo: David Dixon/Creative CommonsJust after Bourton-on-the-Hill is the Quarry Service Station. Photo: David Dixon/Creative Commons I suppose I could say something about Broadway which we come to after we’ve levelled out at the bottom of the hill although we don’t quite as we by-pass it. It is a thoroughly Cotswolds place which is appreciated by most although not by J.B. Priestley on his ‘English Journey’ pilgrimage of 1933 when he suggested it was ‘at Ye Olde game’. If you’re unsure on the meaning you could do worse than filch a copy of Priestley’s seminal book as it’s probably the best UK travel book ever written. To be fair, the town where I live has a ‘Ye Olde Eight Bells Shoppe’ (every town should have one)

Evesham's Booth Hall is one of the town's most notable buildings, late-15th century and beautifully restored to show off its close timberwork to best advantage. Photo: Nilfanion/Creative CommonsEvesham’s Booth Hall is one of the town’s most notable buildings, late-15th century and beautifully restored to show off its close timberwork to best advantage. Photo: Nilfanion/Creative Commons I’m concerned as I seem to have started digressing and waffling. It’s time to get back on track which means completing the run to Evesham which will have special resonance for me and will explain why Route 44 is so familiar. First though we pass through Wickhamford where there’s a nice farm shop and café which has helped me out with sustenance on quite a few occasions. I press on to meet the Evesham bypass which I cross to descend into the town, the town where I grew up and was schooled. Having become a Cotswolds emigrée I would oft travel this way from my new home to visit a Roberts or three; I no longer have that familial umbilical drawing me back. It’s still a place that shaped me for better or worse; home, school, history (including a battlefield and ruined abbey) and Evesham United FC. The royal story that was so prevalent earlier at Woodstock is with us again here for that battle was won by Prince Edward, the future Edward I, who’d prove to be one of our greatest martial monarchs.

References

Chambers Biographical Dictionary (1974)

The Shell Guide to England (Ed. J. Hadfield, 1973)

The Complete Driver’s Atlas of Britain and Ireland (Reader’s Digest)

English Journey (J.B. Priestley, 1934)





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