The next day, The Boss and Sandy leave the pigs in the castle — whose it is they never discover — and they set out again. Shortly thereafter, they meet a band of pilgrims who are headed toward the Valley of Holiness — a place where the holiness of the monks and the prayers of a holy abbot once brought forth a stream of water in a desert. Some time later, the monks persuaded the abbot to build a bath, and they bathed in it; this caused the well to dry up. Once the bath was destroyed, however, the stream sprang forth again.
In the afternoon, The Boss and Sandy overtake another, less cheerful group, a procession of slaves being herded by a slavemaster who goads them along with his whip. The Boss would like to free them all immediately, but he feels that he cannot change things too quickly.
The following morning, they meet another of the salesmen-knights, who tells them that business has been fine and that the well at the Valley of Holiness has dried up again. The monks have sent to Camelot to see if The Boss would come; if he could not, Merlin was invited. Merlin has been there for three days, working on the problem. On hearing this news, The Boss writes an order for materials and assistance, and he sends this knight off to Camelot, urging him to go swiftly. He plans to continue on to the Valley of Holiness.
The Boss and Sandy reach the monastery by nightfall, and the abbot rejoices that The Boss has come. Indeed, the abbot urges him to begin work immediately, but The Boss demurs, saying that it would not be right for him to do anything until Merlin has admitted defeat. Yet, even though The Boss will not take charge, the monastery is much cheered by his arrival, and for the first time in the week and a half since the well dried up, there is a good deal of food and drink and merriment that night.
The next day, The Boss examines the fountain, which is an ordinary well, dug and walled up in the ordinary way. He suspects that the well has sprung a leak; so he has the monks lower him into the well; there, he finds a huge hole in the wall of the well, and he begins to plan his campaign to restore the well. His first point is to suggest how difficult it will be to do so; it is good for business.
He talks with Sandy about the hermits, and afterward, they visit the various hermits during the afternoon. One of them rapidly bows to his feet almost continuously; later, The Boss uses him to supply the power to run a sewing machine that produces shirts.
About noon on Saturday, Merlin makes his last great effort. When that fails, he predicts that no one will ever be able to make the fountain flow again. The abbot is most upset, but The Boss suggests that there is still a chance that he might be able to do something.
That evening, the two men sent by Clarence in response to The Boss's request arrive with the equipment which The Boss needs — "tools, pump, lead pipe, Greek fire, sheaves of big rockets, Roman candles, colored fire sprays, electric apparatus, and a lot of sundries." Toward midnight, after a nap, they go out to the well, and by sunrise they have the well repaired and everything in place for the miracle. By noon, the water in the well has risen to its customary level. They build a platform, arrange the Greek fire at the corners, prepare the rockets, and fence off the area around the platform.
The performance begins at 10:30 with the arrival of the abbot's procession; masses of people have come to see what will happen. Finally, The Boss stands up and begins to pronounce long, strange words in German, lighting a Greek fire at the end of each name. Finally, he pronounces the name of the spirit that has shut off the water supply and sets off the hogshead of rockets. By the glare of the rockets, the crowd sees the water gushing forth from the chapel.
In Chapter 21, The Boss meets a group of pilgrims, and he is surprised to see that the procession includes people from all occupations, professions, and social ranks. Twain is obviously echoing here the pilgrims of Chaucer's famous Canterbury Tales. In this tale, the only way that people of different social classes and different occupations could be found in each other's company was by their making a religious pilgrimage. Also, Chaucer's group of pilgrims were very much like these pilgrims; that is, they are a "pleasant, friendly, sociable herd; pious, happy, merry, and full of unconscious coarseness and innocent indecencies." The prude in the Yankee emerges, and he is offended by the vulgarity which he hears. The description of the pilgrims, then, continues Twain's double vision of the people of this country — innocent, yet indecent by nineteenth-century standards.
In contrast to the pilgrims, the treatment of the group of slaves anticipates Chapter 34, where The Boss and King Arthur will be captured and made slaves themselves. Thus, here, while The Boss wants to do away with slavery, the abolition must wait until King Arthur himself has felt the yoke of slavery.
While religion often comes under criticism in this novel, the most sustained criticism on religion occurs in these chapters, during The Boss's visit to the Valley of Holiness. In other parts of the novel, Twain constantly attacks the authoritarianism of the Roman Catholic Church, but here, his views are more concentrated; he sees the Church as being undemocratic, despotic, and absolutist. He also sees it as being hypocritical in its complete support of the aristocracy. Furthermore, the Church even aids the nobility in pillaging from the peasants and other commoners, but mainly, it fosters ignorance and superstitions. At the end of the novel, the Church is able to play upon the superstitions of the people in Chapter 41 ("Interdict") in order to regain control of the country and to eject The Boss from his position of authority.
The first aspect to come under attack is the absurdity found in making a pilgrimage to worship hermits, many of whom will ultimately become saints. For Twain, a hermit (and also a saint) is, by definition, an abnormal person — a weirdo. That people would come and worship such strange, bizarre people is totally confusing to The Boss. The rationale behind worshipping someone who lives on nuts and berries and goes naked is beyond his Yankee common sense. Living the life of a hermit — that is, living in pure asceticism — contributes nothing to material progress or to the betterment of humanity, and rather than being worshipped, these strange creatures should be ridiculed. Thus, to illustrate his denunciation of this type of asceticism, The Boss is extremely critical of the hermit who sits on a pillar sixty feet high and spends the entire day "bowing his body ceaselessly and rapidly almost to his feet." Because of his large pillar, this hermit will later be known as St. Stylite. The practical Connecticut Yankee sees this movement as being wasted power; thus, he creates a method of attaching a power take-off to the hermit which will, by his incessant motions, create enough power to run a sewing machine which will, in turn, produce "genuine St. Stylite" shirts. At least something practical is attained because of the hermit's useless, and heretofore non-productive, bowing. Other hermits are shown doing equally useless things, and yet being worshipped for doing them.
Twain also pokes good-natured fun by some sly or indecent observations — such as the monastery being on one hill and the nunnery (or convent) on the other hill, and in between the two lies the home for foundlings, implying that the latter place is filled with the children of the monks and nuns.
The Boss's desire for theatricality is shown again in the miracle which he performs in the Valley of Holiness. After he has used his Yankee practicality to patch up the hole in the well, he then has hordes of people gather for the "miracle," which is accompanied by "Greek fires" and "Roman candles" — names given to fireworks, but, one should note, pagan names used to celebrate a Christian miracle. The people are awed, and The Boss, greatly to his satisfaction, is elevated in the sight of everyone present. Ironically, The Boss has once again used superstition to gain control over superstitious people whom he wants to educate not to be superstitious.