Middle Ages Tapestry depicting many folk in period dress with dogs and spears ready to hunt bear and boar.

Boar and Bear Hunt, from Devonshire Hunting Tapestries in V & A Museum, late 1420s.

Middle Ages English Literature: Medieval Era

Though I have read and do enjoy much English literature from the Middle Ages, I wanted to consult someone who has wider expertise than I have when making this list of the greatest literature of the Middle Ages. Therefore, I called on my friend Adam, who earned his Ph.D. in English with concentrations in both Medieval and Renaissance literature.  The list I’m sharing here consists of Adam’s picks of the most significant, and enjoyable, literature from the Middle Ages. I quote the remarks Adam made about each of his choices, identified as his, in quotation marks. Chalk up the rest of the notes to me, MJ.

Enjoy this tour of great and famous English literature of the Middle Ages. Thanks Adam!

Free Online Sources of Middle Ages English Literature:

Project Gutenberg


Search online by title for other sources.

Post by MJ with Useful Information about Middle Ages English Literature.

Significant Historical Dates:

1066 Battle of Hastings: William the Conqueror, Duke of French Normandy, defeats last Anglo-Saxon King, Harold II, establishing the feudal system in England.
1095: Pope Urban II declares first Crusade.
1170: Archbishop of Canterbury is murdered, showing conflict between church and monarch of England
1215: Declaration of Magna Carta, restricting power of the monarch; first step toward constitutional government in England
1315-17: Great Famine in Northern Europe
1320: Dante completes The Divine Comedy
1337-1453: Hundred Years’ War between England and France
1347-51: Black Death (bubonic plaque), one of the largest pandemics in human history
1415: Henry V defeats the French at Agincourt
1439: In Germany, Gutenberg invents the printing press with movable type: begins a revolution in book printing and spread of information
1476: William Caxton sets up printing shop in Westminster in England.
1485: Richard III is defeated in battle of Bosworth, ending reign of Plantagenet family and beginning reign of Tudor monarchs.
1485:  William Caxton prints Malory’s Morte D’Arthur, one of first books printed in England

English Literature from 1066-1485:

Full length portrait of Chaucer from Medieval book illustration, showing figure in brown robe and headdress against white background.

Portrait of Chaucer

Chaucer, Canterbury Tales, 1387-1400

Almost everyone familiar with Western literature has heard of The Canterbury Tales, and even read one or more of them in school. One of the first major works written in English, Canterbury Tales tells the story of 30 different people from all walks of medieval society who are going on a religious pilgrimage together.

The “host,” the leader of the party, asks each person to tell different tales to help them all pass the time on the road. The resulting stories, each told from the point of view of a different pilgrim, are sourced from many different genres of Medieval literature; each is related with the unique “spin” or point of view of each separate character, showing the personalities and values of each. This adds a layer of extra interest to each separate story.

Chaucer seems to have intended for each character to relate two tales, but he never finished all of them. Even so, there are plenty of wonderful tales to read, from the “Prologue,” which sweetly and humorously describes each of the people in the traveling party, to tales of love, courage, or just plain ribaldry.

You can read Canterbury Tales in a modern translation or attempt them in the original Middle English. The language spoken in Chaucer’s day is quite a bit different from modern English, but though strange at first, it gets easier to read as you read more of it. In the original language, the sound of Chaucer’s poetry is just beautiful.

Adam remarks, “Canterbury Tales demonstrates (among much else!) the medieval fascination with juxtaposition and first-person point of view. Both techniques emphasize ways of seeing and humanity’s limited vantage. If I were to suggest to readers just one tale, I would choose the ‘Nun’s Priest’s Tale.’ It reworks the preceding tales, parodies many genres, includes many of Chaucer’s favorite themes (marriage, gender, desire, knowledge, literature), and it’s hilarious.

“The Tales as a whole make a wonderful contrast with Dante’s Divine Comedy (which Chaucer knew): both works feature first-person narrator pilgrims, but they describe very different journeys. Dante’s cosmic journey involves judging everyone, placing them in heaven, purgatory, or hell, but Chaucer’s more modest, forty-mile pilgrimage asks only us as readers to judge his characters, although it doesn’t make that process straightforward (not that I would call Dante straightforward, exactly!).”

Photograph of Canterbury Cathedral, destination for Chaucer's Pilgrim characters.

Canterbury Cathedral, destination for Chaucer’s Pilgrim characters.

John Gower, Confessio Amantis, 1390

Adam remarks, “Like the Canterbury Tales, Gower’s huge Confessio Amantis is a collection of stories in a first-person narrative frame.”

Gower was a friend of Chaucer who admired his work. According to a great site on literature, Interestingliterature.com, “A long poem comprising a number of smaller stories, Confessio Amantis (written in the early 1390s) takes as its theme the idea of courtly love – the poem’s title means ‘the lover’s confession’. But the ‘confession’ part of the title also points up its other theme or interest: Christianity and moral virtue. How can a courtly lover also be a good Christian? The poem explores the themes of morality and love through a host of stories. . ..”

Check out Interesting Literature for more commentary on Confessio Amantis.

Beautiful stained glass in shades of brown and blue depicting author William Langland, reclining in contemplation near a brook.

Author William Langland depicted in stained glass, Church of St Mary the Virgin in Cleobury Mortimer, Shropshire.

William Langland, Piers Ploughman, 1370-90

Piers Ploughman was written by a clergyman. It describes a series of dreams or visions in which the dreamer, Will, questions how his soul may be saved, also engaging in much social commentary and critique as he seeks wisdom on how to lead the best life. In dreams, he meets many different allegorical characters and converses with them, including such characters as “Scripture,” “Learning,” and each of the Seven Deadly Sins. Piers Ploughman is both a work of devotion and a description of Medieval society as Langland saw it.

Adam remarks,Piers Ploughman makes an interesting contrast with Chaucer (another first-person pilgrimage) but is also fascinating on its own right. Both Chaucer and Langland emphasize humanity’s imperfect knowledge, but Langland isn’t as funny. Chaucer seems more comfortable than Langland with the mysteries of life, with ‘not knowing.’ Also, Langland doesn’t delight in humanity’s imperfection as much as Chaucer.”

MJ remarks: Langland is more critical of humankind than Chaucer, seeming quite disturbed by the sin and evil-doing he finds in the world around him.

Julian of Norwich, Revelations of Divine Love, 1373

Statue showing head and torso of Julian of Norwich. She is holding her famous work, Revelations of Divine Love.

Statue commemorating Julian of Norwich with her famous work.

Julian of Norwich was a 14th century anchoress, which meant she chose a solitary life of prayer and contemplation, walled within a small cell from which she spoke to people only on rare occasions. According to the British Library, at least 100 women chose this life from the 14th through the 16th centuries. Julian is unique in that she wrote an account of her visions of God and the bleeding Christ, which communicated to her the complete, eternal, continuing love of God. Many Christians in the modern day are still inspired and reassured by her accounts of the loving God revealed in this work.

(Read more about the life of Middle Ages anchorites on the British Library site here.)

Adam remarks, “Julian of Norwich is often identified as the first woman writer in English. As an anchoress, Julian lived in a cell attached to a cathedral [in this case, St. Julian’s Church in Norwich]. As a female mystic, she was also both inside and outside the church, especially because her text seems by turns orthodox and heretical. At times she seems to believe in universal salvation [a heretical belief].

The Book of Margery Kempe, late 1430s

According to The British Library,

“The Book of Margery Kempe is the earliest autobiography in English.
“Margery Kempe lived in the East Anglian town of Lynn in the early 15th century, and was at various times the owner of a horse-mill and a brewer, but later in her life she became a visionary and mystic. She was also the mother of 14 children.”

Being unable to write herself, Kempe dictated her book to a scribe, detailing her critique of medieval town values and how she ultimately gave up her secure position in society to devote herself to a religious life. It’s interesting that Marjory Kempe went to visit Julian, and reports on this conversation in her book.

Adam remarks, “Kempe and Julian [of Norwich] make an obvious contrast because they were roughly contemporary female mystics. Although Julian was younger and perhaps more radical [when she wrote her works], she didn’t seem to experience any censure, whereas [the younger] Margery Kempe got in trouble with authorities for her visions. This suggests that late fourteenth-century England [when Julian was first writing] was maybe a bit more tolerant than the early fifteenth, which persecuted the proto-Protestant Lollards.”

Find a text of The Book of Margery Kempe here.

Mystery Plays (mid-1300s through 1400s)

Mystery plays began as a way to present Bible stories and religious teachings during religious festivals. The plays were often presented as complete cycles that together told the whole story of the universe, from Creation to Judgement. Early plays were presented in Latin, but by the mid-1300s, various guilds were acting in plays using English, often presenting them away from the church grounds. Being away from the church allowed many kinds of non-religious elements to creep in gradually, until these plays became as humorous or satirical as they were devotional. Check out the British Library’s site for great information about Mystery Plays. 

Adam remarks, “It’s hard to know where to begin to list the mystery plays, but ‘The Second Shepherd’s Play,’ for one, is hilarious. The mystery plays—free, amateur, no identified author, played all across the country, grouped in huge cycles together depicting the Christian story—contrast with the Renaissance drama that came later [during Shakespeare’s time—MJ note]. Renaissance dramas had admission prices, were professional, more clearly authored, centered in London, policed and policing. Some medievalists point out that from this angle, the Renaissance drama tradition looks more repressive than the medieval.”

Morality Plays, 1400s through early 1500s

According to the editors of the Encyclopedia Britannica, “Morality play, also called morality, an allegorical drama popular in Europe especially during the 15th and 16th centuries, in which the characters personify moral qualities (such as charity or vice) or abstractions (as death or youth) and in which moral lessons are taught.”

Adam remarks, “’Everyman’ seems to be the most canonical morality play, but there’s also The Castle of Perseverence, Mankind, and Wisdom. Renaissance characters like Iago and Falstaff [who appear much later in Shakespeare’s plays] owe something to morality play vice figures. Allegory is popular in the Middle Ages, perhaps party because, like romance [see next two entries in list for examples of romance], it involves the reader in trying to decipher a fallen world.”

Close-up photo of knight in medieval armor, raising his sword in his right hand.

Armored Knight

Malory, Works (England’s first printer, William Caxton, later applied the title Le Morte D’Arthur), 1485

Malory’s work recounts, in English, the adventures of the legendary King Arthur, telling the tales of Lancelot, Guinevere, Merlin, and the Knights of the Round Table. The Arthur legends were very old at the time Malory was writing, going back to a time before the Norman Invasion in 1066. Before Malory penned his work, Chrétién de Troyes had written a popular version of the Arthur tales in French, which Malory may have taken as a starting point.

Le Morte D’Arthur is a good example of a medieval romance. Adam remarks, “Romance is a central medieval genre: it emphasizes questing, a fallen world full of strange signs, the dream of reintegration and wholeness. Romance also often reinforces an aristocratic worldview full of warfare and adventure, rather than focusing on everyday hardship.”

Sir Gawain and the Green Knight, late 14th century

The anonymous writer of this romance most likely came from Britain’s Northwest Midlands, given the dialect he employs, according to SparkNotes.

The romance tale of Sir Gawain being challenged by the Green Knight is one of the most readable and interesting stories in Medieval literature. It begins when a mysterious Green Knight arrives during a celebration at King Arthur’s table. He challenges any knight to take his axe and deliver him one blow, in return for the Green Knight doing the same to him, one whole year later. Arthur’s nephew Gawain accepts the challenge, delivers a blow that takes the Green Knight’s head off, then watches in dismay as he picks up his head and walks out, after setting the meeting place with Gawain in exactly one year.

If you want to know what happens next, and a lot of things do happen, read this rich tale that also examines the application of the Chivalric code revered by knights of the era.

Adam remarks: “’Sir Gawain’ is another piece of literature with an amazingly intricate structure. The poem has so much going on that it’s hard to say just one interesting thing. One important point: the story does demonstrate the classic outward journey into the marvelous world and return home that romance so often relies on. At the end, Gawain feels ashamed that he doesn’t quite pass the test perfectly (and perhaps no one could’ve, since no one is perfect), but his shame also adds an important piece to the chivalric code: Christianity [one guiding set of values in the Middle Ages] encourages guilt, which is inward; but military societies rely on honor and shame; guilt is inward, shame outward.”

“Pearl” (by the Gawain poet), late 14th century

“Pearl” is a lovely and intricate poem found in the same manuscript that includes Sir Gawain, written by the same poet. The speaker in the poem, who has recently lost a child, has a vision in which he visits a different land and sees his child “Perle” again. The poem relies on much New Testament symbolism as well as numerology. According to the British Library, “The poem is 1,212 lines long and is composed of 12-line stanzas. This is in homage to the heavenly Jerusalem which is 12 furlongs long, and to its 12 gates, each of which are set with pearls.”

Adam remarks, “’The Pearl’ demonstrates medieval literature’s delight in structure, which reflects medieval people’s belief in an ordered cosmos, even if they can’t perceive that order.”

Josephine Livingstone wrote an interesting commentary on this poem in an article reviewing a new translation of “Pearl” by Simon Armitage. Also, check out this summary on Interestingliterature.com. 

Robert Henryson, Morall Fabillis (Moral Fables) and Testament of Cresseid, c. 1460-1500

Adam remarks, “Scottish writer Henryson admired Chaucer and wrote his own [tragic] version of Cressida’s story, unlike Chaucer’s version. Chaucer’s version (Troilus and Criseyde, which many Chaucerians consider his greatest work) is the only sympathetic treatment of Cressida in medieval or early modern literature.”

Moral Fables consists of 13 different fables written in 7-line stanzas, humorously told, each with their own moral, something like Aesop’s fables. If you’d like to take a peek at Henryson, try this free translation by R. W. Smith, online.

Seamus Heaney, poet and translator of Beowulf, has also done a translation of some of Henryson’s work.

William Dunbar, “Lament for the Makaris (Lament for the Makers),” 1505

This poem laments death in general, as well as mourning a long list of poets and writers (the “Makers”) who have lost their lives.

Adam remarks, “Dunbar is another Scottish inheritor of Chaucer. ‘Lament’ is one of his more famous and moving poems, with its refrain that ends each verse, Timor mortis conturbat me, meaning ‘fear of death disturbs/frightens/overwhelms/confuses me.’”
(Note: “The phrase comes from a responsory of the Catholic Office of the Dead,” according the Wikipedia. 

You can find texts of this poem online.

Large red tapestry depicting a lady and her servant, flanked by a lion, a unicorn, and multiple trees and animals, illustrating the magical realm of the Medieval Romance.

“A Mon Seul Desir” tapestry, illustrating the magical realm of Medieval Romance.

We hope you have enjoyed this tour through Middle Ages English Literature!

Here are links to lists of great literature from other periods:

Old English Literature

Index to Literary Classics Timelines on Read Great Literature


*Photo Credits

Boar and Bear Hunt Tapestry.  The original uploader was VAwebteam at English Wikipedia. [CC BY-SA 3.0 ], via Wikimedia Commons.

Chaucer Portrait. British Library [Public Domain. CC0] Via Wikimedia Commons.

Canterbury Cathedral. By Hans Musil – Picture taken and postprocessed by Hans Musil., CC BY-SA 4.0, Via Wikimedia Commons.

William Langland stained glass portrait. By Lepidus Magnus – Own work, CC BY-SA 4.0, via Wikimedia Commons.

Julian of Norwich Statue. rocketjohn [CC BY-SA 2.0 ], via Wikimedia Commons.

Knight in armor. Photo by Maria Pop from Pexels.

A Mon Seul Desir tapestry. Musée de Cluny – Musée national du Moyen Âge [Public domain] via Wikimedia Commons.