After a recitation of the prologue to The Canterbury Tales, the film cuts to the modern day and modern "pilgrims". There are, as it happens, three pilgrims to Canterbury, all of whom have stopped off at the fictional village of Chillingbourne in Kent. They symbolize aspects of the Allied war effort circa 1943:
- British Army Sgt. Peter Gibbs. A trained organist before the war, his unit has been undergoing training in the fields around Chillingbourne. He is about to leave for Canterbury with his unit, which from there will go off to war.
- American Sgt. Bob Johnson. He's on leave and going to Canterbury as a tourist. He gets off at the Chillingbourne train station by mistake. He's irritated because his girlfriend back home hasn't written him for weeks.
- British civilian Alison Smith, who has joined the "Women's Land Army", a volunteer organization that sends women off to the country to work as farm laborers, doing work that's not being done by men now in the armed forces. She has been assigned to a Chillingbourne farm, but intends to go to Canterbury on her day off to check on her camper, which has been in storage in a Canterbury garage since 1940. She had a fiance, Geoffrey, who was killed in the war.
The three "pilgrims" are brought together by a peculiar incident. As they get off the train at Chillingbourne, Alison is attacked by a man who dumps glue into her hair. Peter, Bob, and Alison find out that the "Glue Man" has done this repeatedly to a lot of local girls. They look into the case and find a most unusual suspect: the eminently respectable local justice of the peace, Thomas Colpeper (Eric Portman).
All this is really just an excuse for a meditation on the beauty of the English countryside, the history of England and how the past resonates in the modern day, and how the English nation has rallied to fight Hitler.
Filled with a cast of unknowns. John Sweet, who played Sgt. Johnson, was a real American sergeant who never appeared in another movie. Sheila Sim (Alison) and Dennis Price (Peter) both made their film debuts, and both became huge stars. Charles Hawtrey, later a star of the Carry On film series, appears as the cranky railroad station master.
- Ask a Stupid Question...: Peter climbs up to the Canterbury cathedral organ. He sees the organist futzing around with sheet music and asks if he's the organist. The organist shoots back with "Do I look like a charwoman?"
- Background Halo: On the train to Canterbury, Peter says "I'll believe that when I see a halo round my head." At once, the train passes into a patch of sunlight, backlighting him and giving the appearance of a halo.
- Book Ends: The same scene of ringing church bells followed by a shot of Canterbury Cathedral plays at the beginning and the end.
- Brits Love Tea: Part of Bob's Culture Clash is his inability to fathom the English devotion to tea. His buddy, who has become a convert, basically forces Bob to sit down and have some.
- Cobweb of Disuse: Alison's camper, in storage for three years. It also has gotten infested with moths. Alison, who took a vacation in the camper with Geoffrey before the war, breaks down crying.
- Culture Clash: Bob's a nice fellow but he's continually bemused by the peculiarities of English country folk. Like when his landlady flatly refuses to give him coffee for breakfast but insists on serving him tea.
- Face Framed in Shadow: Alison as she looks into the dark interior of the camper, filled with memories of her time with Geoffrey.
- Impairment Shot: Alison's vision blurs when she is told that Geoffrey is not dead after all but is alive on Gibraltar. She barely manages to avoid fainting.
- Let Off by the Detective: Our heroes wind up letting Colpeper off the hook after unmasking him as the Glue Man. He really doesn't even have a very good excuse—terrorizing the local women to keep them from dating soldiers, thus leading the bored soldiers to finally attend his history lectures. But they let him go anyway.
- Match Cut: A famous one that also serves as a 600-year Time Skip. The opening shows 14th-century pilgrims on the road to Canterbury. A falconer lets his falcon loose. There's a shot of the falcon soaring in the air. Then there's a cut to a shot of a fighter plane from the same perspective, letting us know we're in 1943. Very similiar to the iconic Match Cut in 2001: A Space Odyssey, although if Stanley Kubrick stole the idea from this movie, he never admitted it.
- Mythology Gag: It can't be a coincidence that the lead female character in the film is named "Alison", the name of a character from "The Miller's Tale", the most famous of the Canterbury Tales.
- Power Trio: Our three leads, who solve the "Glue Man" mystery.
- Recycled Soundtrack: Composer Allan Gray reused part of the score for one of his earlier Powell & Pressburger films, The Life and Death of Colonel Blimp. The distinctive jazz trumpet of the tune heard over the early dispatch rider scene is now used in the background in the scene in the Hand of Glory tavern when Sergeant Gibbs is telling Sergeant Johnson how he has identified the Glueman via the air raid warden timetable.
- Reports of My Death Were Greatly Exaggerated: As it turns out, Geoffrey isn't dead. He wasn't killed in combat but is alive and in Gibraltar.
- Separated by a Common Language: Bob runs into this problem. He asks the local kids where the "drugstore" is. They draw a blank. He explains that it's the place where you go to buy everyday stuff like toothpaste or shaving cream or (most importantly) glue. One of the kids says "Oh, you mean the grocer's." Later the same kid corrects Bob again for saying "drugstore". He also tells Bob two different times that a quarter should be called a "shilling".
- Shout-Out: The film opens with the opening prologue from The Canterbury Tales. Then the narrator talks about how little the English countryside has changed and how modern pilgrims still go to Canterbury—all in the same style of rhyming verse that Chaucer used.
- Slice of Life: There's sort of a plot, mostly the pursuit of the "Glue Man", but the film's really a meditation on life in the English countryside during the war.
- Standard Snippet: What does Peter play when he fulfills a lifelong dream by playing a grand church organ? Toccata and Fugue in D minor, that's what.
- Time Skip: Six hundred years or so from the opening prologue of medieval Canterbury pilgrims to the modern day.