Inspired by one of the English language's seminal works, 24 modern-day pilgrims – including two from China and one from Bermuda – braved piercing April 'shoures' to undertake a full-scale re-enactment Chaucer's masterpiece, acting out the tales as they travelled on foot to Canterbury in aid of the National Literacy Trust Join Henry Eliot – aka the Host, Harry Bailly – for a dazzling account, featuring pictures, audio and video, of a pilgrimage in the literary footsteps of one of Britain's greatest poets

General prologue

On Wednesday 18 April, I stood in Talbot Yard off Borough High Street in London getting wet: an April shoure soote was piercing me to the roote. In 1387 the fictional pilgrims in Geoffrey Chaucer's Canterbury Tales assembled on this same spot in what was then the yard of the Tabard Inn, before riding to Canterbury Cathedral to visit the shrine of Thomas à Becket. Along the way, of course, they told the stories that form the greatest work of literature in the English language.

'An April shoure soote was piercing me to the roote' ... Chaucer plaque in Talbot Yard, London. Photograph: Henry Eliot

This morning another, real band of pilgrims was assembling for a second attempt at the Canterbury Tales: 625 years later to the day, we would walk from Southwark to Canterbury, staying in medieval pilgrim towns, telling Chaucer's tales and raising money for the National Literacy Trust. Already they were gathering: the Man of Law and the Prioress splashing across the yard; the Nun's Priest in an anorak; the Miller in red; and here was Chaucer himself brandishing a pair of sprung walking poles.

The idea had come from wanting to hear all the tales in one go. The fun of the Canterbury Tales is in the banter between the pilgrims, but when you read the stories in isolation you can lose that sense of a multi-voiced, rambunctious group. It seemed an obvious leap to hear all the tales with their links, and place them geographically along the road to Canterbury as well.

If you're reading on mobile, click here to listen to an audio clip of the opening lines.

We were an eclectic group – but then so was Chaucer's compaignye of sundry folk. I'd sent invitations widely with no idea who would actually be joining me. Among us were teachers, actors, academics, journalists, civil servants, theatre directors and even a trainee doctor of physic. Four pilgrims were over 50, two came from China and one from Bermuda.

As in the poem, we'd met at dinner the night before. We'd eaten a medieval meal in a low-ceilinged room of the George Inn, overlooking Talbot Yard, and become of one another's felaweshipe. There were 24 of us, each taking a character and the appropriate tale. I was playing Harry Bailly, the host of the event, and as such was guiding the pilgrims, organising accommodation and vitaille and, most importantly, managing the tale-telling.

We'd been addressed at the meal by Professor Helen Cooper, the country's leading Chaucerian scholar, who had bridged the gap brilliantly between those who knew the poem well and those who were still "in outer darkness", and we had drunk ypocras, a medieval spiced wine I'd been preparing for several weeks. It tasted like mulled Benylin and the high nutmeg content gave people hallucinations, but it wasn't undrinkable.

Inspired by Professor Cooper and perhaps the nutmeg, this morning we were ready for an exploit that as far as we knew had never been attempted before. After a photo under the blue plaque, we set off through the throng of damp commuters, heading south-east out of London on the 65-mile route to Canterbury.

To Caunterbury they wende …

A well-signposted start. Photograph: Henry Eliot

The Thomas a Becket on the Old Kent Road is a "boxer's pub", famous for the ring where Henry Cooper fought and trained, but it also marks the site of an ancient stream, the St Thomas a Watering, where Chaucer's pilgrims drew cuts to select their first storyteller.

The Knight was up first and we went inside the historic boozer to hear his story. Huw Moore, a civil servant when not fighting mortal batailles, got the tales off to a rip-roaring start by turning the lengthy and ponderous Knight's Tale into a pantomime with full-audience participation.

Reliving The Knight's Tale. Photograph: Henry Eliot

The Theban love triangle between Arcite, Palamon and Emily has never been so funny.

The first day was a long slog out of London, but there were moments of asphalt relief. Greenwich Park was a welcome oasis and we stopped to hear the Miller's Tale over a picnic lunch. Although it seemed wrong somehow to be eating a flapjack while Absolon kissed Alison's naked ers ful savourly …

If you're reading on mobile, click here to listen to an audio clip of the Miller's Tale.

In the 1380s, most of the country between London and Canterbury was thickly forested and pilgrims would have stuck closely to Watling Street, paved by the Romans in roughly a straight line from Dover to London. Unfortunately, today Watling Street is the A2 and mostly very unpleasant walking. Our get-out clause was that by the 14th century the Roman paving had become so dilapidated and the highway so dangerous that pilgrims often adopted parallel routes on country paths and green lanes, so we felt justified in avoiding the exhaust fumes whenever we could.

Pilgrims walking. Photograph: Henry Eliot

The Reeve told his tale in front of Severndroog Castle in the heart of ancient Oxleas Woods and the Cook scratched his ulcerous mormal in the rolling parkland of Danson House.

Any walk throws up serendipitous encounters, but our unusual endeavour seemed to unlock even more than normal. We were merely passing William Morris's Red House in Bexleyheath when we got into conversation with the curator and were immediately treated to an impromptu after-hours tour. Morris was obsessed with Chaucer, we were told, and had built the Red House as near the pilgrimage route as he could. Chaucerian references recurred throughout his home; apparently he even swore in Chaucerian expletives.

One of the problems I'd had when distributing tales was the danger of offending anyone by assigning them one of Chaucer's more unsavoury characters. Perhaps this is why my mother ended up playing the Wife of Bath. She is from Bath, so it seemed appropriate, but unlike the wyf she's only had one husband, and he's not called Jenkyn. She told her tale in an 18th-century hostelry in Dartford, our first overnight stop.

Beyond the M25

The next morning, after we'd discovered what women love moost, we left Dartford and crossed the M25, throwing off the last of the London sprawl. Walking as a company over a number of days made for a fluid group dynamic: you dropped in and out of conversation and either enjoyed the company or walked stretches alone. It was a great pace at which to hear the tales as well, with time to chat about each one and time to look forward to the next.

Darnley mausoleum. Photograph: Henry Eliot

We walked between Kentish villages, along field-side paths. The Friar and the Summoner told tales about each other: a wicked summoner is claimed by the devil and a greedy friar receives a terrible fart amydde his hand while groping for money in a man's anus. Ed Posnett, who works for a professional services company, told the Summoner's Tale and enlisted the Reeve's help to produce an appropriately buttock-blasting sound effect.

One of our most unusual stopping points was the extraordinary Darnley Mausoleum in the heart of Cobham Woods, a huge white-stone pyramid tomb, which appears through the trees like a mirage as you approach. The Prioress told her brutal tale about a murdered schoolboy who sings his Alma Redemptoris despite being dead. Sarah Lambie told the tale with the aid of a specially prepared sock puppet and used a zip to kitte the boy's throte.

The Prioress and a sock puppet. Photograph: Henry Eliot

Reaching Rochester

The arrival in Rochester on the second evening was dramatic. As you cross the bridge, the castle and the cathedral stand like giants over the old city and that day they were picked out in gold by the afternoon sun, while the sky behind was a deep, bruised purple.

Chaucer writes himself into his own pilgrimage and Adam Crick, teacher, river-swimmer and polymath, rose brilliantly to the metatextual challenge of playing both a pilgrim and the author of the whole enterprise. When Chaucer the character begins a rym dogerel about a knight called Sir Thopas, Chaucer the author, with self-deprecating wit, has the Host cut him off mid-verse: "Thy drasty rymyng is nat worth a toord!" As a palliative he then tells the long-winded prose Tale of Melibee, which is hardly better, but Adam turned it into a boisterous farce with multiple audience sound effects.

On Friday morning, Gele Bai, a Chinese masters student studying English in London, gave us the Monk's Tale beneath the walls of Rochester Castle. The thought of doing the equivalent – reciting classical Chinese literature in a group of native speakers – filled me with respect. We then we set off along the shore of the Kentish marshes, half expecting Magwitch to appear at any moment. Chaucer country overlapped with Dickens country here: we'd seen the latter's Swiss chalet in Rochester, where he wrote five of his novels, and also the building that inspired Miss Havisham's Satis House. The day was sunny and the water sparkled all the way to Kingsnorth power station on the Hoo Peninsula.

Upon Kentish marshes. Photograph: Henry Eliot

After lunch the path passed right through a massive brood of chickens. This was the only place to hear the Nun's Priest's Tale of Chanticleer, the gentil cok, who crowed better than any other rooster. Will Gould, a primary school teacher, got through the farmyard story of clever Chanticleer outwitting the fox, despite a deafening chorus of purling chickens, who, growing inquisitive, began to pluck at our boots and bare legs.

If you're reading on mobile, click here to watch the Nun Priest's Tale video.

Wending past St Mary's Newington and over the railway line, we heard the Doctor of Physic's Tale in the car park of a Sittingbourne general practice, and pushed on to Bapchild, where there was once a holy well dedicated to St Thomas. We looked for the well but it's now a South East Water pump.

Professor Cooper described the Pardoner as "perhaps the pilgrim who comes closest to being evil". We sat on the grass to hear his wonderful (im)moral tale near the remains of Tonge Castle motte, which could as well have been the hill where the three thieves seek death in his story. Matt Evans delivered the sinister story in an intimate and atmospheric circle. Behind him was an epic backdrop of clouds, pendulous and dark, with startling rays of sunlight breaking through.

If you're reading on mobile, click here to watch the Pardoner's Tale video.

The Host condemns the Pardoner at the end of his tale because he has the gall to ask the assembled company for money. In contrast, our real-life sponsors had been extremely generous: we had by then raised over £7,000 – though of course we were supporting a charity, whereas the Pardoner was pocketing cash for a kiss of his bogus relics. The National Literacy Trust was an appropriate charity for us to support, seeing as Chaucer was the first author to write literature in the English language and the first to be printed by Caxton in 1476. The work the Trust does in supporting literacy at all ages across the UK is truly inspirational.

The final push to Faversham

The third day was the longest walk – 21 miles – and the final push to Faversham was tough. After dinner, Jessica Lazar told the Merchant's Tale of January and May, with a full-cast dumbshow involving cross-dressing, rude balloons and shenanigans behind a sheet.

Getting into role for The Merchant's Tale. Photograph: Henry Eliot

In Ospringe, next to Faversham, there is a medieval wayside hospital and hostelry called the Maison Dieu, where pilgrims stayed on their way to Canterbury, and we'd arranged special access. The original larger building complex included a "camera regis", or king's chamber, so Chaucer himself might well have stayed there as a senior diplomat on business to Dover. This was the most evocative space on the entire walk. We stepped back through the centuries when we stepped inside and it didn't seem at all unusual when Alison Stanley, a university lecturer, donned her Second Nun's wimple to tell the Tale of St Cecilia.

The Second Nun's Tale. Photograph: Henry Eliot

Leaving Faversham behind, we made our way to the beautiful village of Boughton under Blean and the White Horse pub.

In the poem, the pilgrims are overtaken by a canon and his yeoman in Boghtoun under Blee. The Canon soon disappears when his servant exposes him as a crook and a swindler, and his Canon's Yeoman is left behind to tell a story in his place. Georgie Gould joined us for the last day and told the story as a news report with a cardboard television on her head.

If you're reading on mobile, click here to watch the Canon Yeoman's Tale video.

First view of Canterbury

The end was in sight now. The final day was just 12 miles' walking, which seemed a breeze. We heard the Manciple's Tale outside St Nicholas Harbledown, a medieval leper hospital, and then descended to the main Canterbury road, where we were greeted with a sight that must have stirred pilgrims' hearts for the last 800 years: the cathedral, scene of St Thomas's martyrdom, heart of the Church of England, rising shimmering and white from the city.

First view of Canterbury. Photograph: Henry Eliot

At St Dunstan's church we stopped with more than half a mile still to walk. St Thomas à Becket was canonised in 1173, barely two years after his death, and one of the first to visit his shrine was King Henry II, who made a pilgrimage of penance to atone for his hand in the death of the "turbulent priest". On that pilgrimage, Henry paused at St Dunstan's to put on a hairshirt and remove his shoes. We hadn't brought hairshirts, but most of us sat on a low wall outside the church and – to the surprise of passers by – eased off our boots, exposing blisters and aching feet to the cool pavement stones. Then we, like King Henry, walked barefoot into Canterbury.

The last tale

Removing shoes for arrival in Canterbury. Photograph: Henry Eliot

"Lordynges everichoon," says the Host, "now lakketh us no tales mo than oon." And he invites the Parson to tell the very last story, which we heard beneath the towers of Westgate, on the boundary line of the medieval walled city of Canterbury. The Westgate is a thoroughfare and Phoebe Dickerson gathered a small crowd, accusing the citizens of Canterbury of lechery and foul language.

The final walk down the high street was momentous. Our feet felt every municipal brick; shoppers goggled at us; we bunched together, a barefoot, mud-splattered band of walkers, unused to crowds. We turned left down narrow Mercery Lane and finally, with the shaky-cam vision of exhaustion, perceived the extraordinary Cathedral Gate, with a massive bronze Christ bending to greet us with open palms.

If you're reading on mobile, click here to watch the pilgrims enter Canterbury barefoot.

Recognised immediately, we were borne by cathedral staff into the precincts – "Canon Clare is expecting you" – and, boots back on, were taken into the building itself, through the nave, the size of which was truly awesome after days of paths and hedgerows, and down into an intimate space in the undercroft, where we were welcomed as pilgrims. It had not been a religious pilgrimage, but Canon Clare's prayers of thanks in the Chapel of Our Lady marked its conclusion in an unexpectedly spiritual way. We all felt part of something bigger than a simple walk.

In Southwark, the Host announces a competition: the pilgrim who tells his tale with best sentence and moost solaas will receive a free meal. So at dinner in the Pilgrims Hotel on the last night, we voted. A hush settled as the results came in … It wasn't quite a gold-envelope moment but in a dramatic turn of events there was a dead heat between Chaucer and the Knight, who shared the prize.

'Here taketh the makere of this book his leve'

Our course was almost run, but there was one last thing to do and a busy restaurant wasn't the place for it. Back at our hotel, on a roof terrace below the glowing flank of the illuminated cathedral, we gathered to hear Chaucer's Retraction, which concludes both the poem and Chaucer's own career. It was a memorable moment under the stars, very quiet and moving, which brought the project to a still and thoughtful close.

If you're reading on mobile, click here to listen to an audio clip of Chaucer's Retraction.

On Sunday, we peeled away in small groups of two or three. Some attended Eucharist in the cathedral; a smaller number met for lunch. There was a sense of emptiness in the dissolving of our esoteric bond. Finally the last train to London was caught, and Chaucer's pilgrims dispersed for only the second time in 700 years.

The pilgrims reach the end. Photograph: Henry Eliot

The pilgrims:

Chaucer – Adam Crick

Knight – Huw Moore

Squire – Bethan Bide

Prioress – Sarah Lambie

Second Nun – Alison Stanley

Nun's Priest – Will Gould

Monk – Gele Bai

Friar – Simon Eliot

Merchant – Jessica Lazar

Clerk – Lucy Hall

Man of Law – Anthony Lambie

Franklin – Matt Spencer

Cook – Jeff James

Shipman – Sarah Brocklehurst

Physician – Chan Yuan

Wife of Bath – Olivia Eliot

Parson – Phoebe Dickerson

Miller – Jacob Goodwin

Manciple – Vikki Newton

Reeve – Patrick Kingsley

Summoner – Ed Posnett

Pardoner – Matt Evans

Canon's Yeoman – Georgie Gould

Harry Bailly – Henry Eliot

@Canterbury2012 – justgiving.com/CanterburyTales2012