The Madness of May

In Short

The Madness of May is a lighthearted 1917 comedic novel following Billy Deering, a distraught young New Yorker facing financial ruin after losing two hundred thousand dollars in bonds. When an enigmatic, philosophizing adventurer named Hood unexpectedly turns up at his house, Billy is dragged into an impromptu spring road trip through the suburbs and countryside. What seems like a chaotic wild-goose chase becomes an elaborate, buoyant journey filled with artful eccentrics, moonlight meetings, unexpected family revelations, and sweet romance. The book remains a delightful, sun-lit escape that celebrates open-air freedom over dreary office routine.

The Story

Desperate and contemplating suicide, Billy Deering arrives at his father’s Westchester County home fearing that his theft of two hundred thousand dollars in negotiable bonds from his family’s banking firm is about to be exposed. Instead of the police, he encounters a mysterious, articulate traveler calling himself Hood. Hood quickly senses Billy's panic, listens to his confession, and reveals that Billy actually mislaid the suitcase containing the fortune at Grand Central Station. Refusing to let Billy call the police or despair further, Hood insists they set off on foot and by automobile to track down the unknown young woman who inadvertently swapped bags with him.

Guided by the arbitrary toss of a slipper toward the northeast, Hood leads the reluctant Billy onto the open road. Along the way, Billy meets a whimsical young woman in a clown costume who hangs a paper-and-lantern moon in a pine tree and calls herself Pierrette. Drawn to her infectious charm, Billy accepts her invitation to breakfast at a nearby bungalow, only to find that she has vanished, leaving behind her studio filled with theatrical sketches and a enigmatic companion named Babette.

As Hood continues to steer their aimless wanderings across Connecticut and New York, the trip turns increasingly surreal. They crashed a dinner party held by a colorful family of aristocrats who write books and play host under theatrical guises. To Billy's utter astonishment, his own sister Constance appears at the house working as a secretary named Smeraldina, and she is secretly in love with Hood’s cheerful chauffeur, Cassowary. Billy also learns that his own father, whom he believed was away in California, has been arrested for speeding in a nearby country town.

When Hood and Billy deliberately get themselves thrown into the local jail to visit the elder Deering, the entire mystery unravels. Hood is actually Robert Tyringham, an eccentric, long-missing heir whose massive estate the elder Deering manages as trustee. Senior Deering confesses that he had temporarily stolen the bonds himself out of fear and temptation before hiding them safely elsewhere, meaning Billy never actually lost his father's client assets. With the misunderstandings cleared, Billy marries Pierrette—whose real name is Roberta, Tyringham’s daughter. Though the family settles into happy domesticity, the pull of the open road lingers, and as May ends, Tyringham quietly slips back out under the stars for another spontaneous adventure.

How It Unfolds

A panic at home Billy Deering arrives at his father’s estate believing his financial theft is discovered, only to find the uninvited and whimsical Hood occupying his guest room.

Setting out by slipper Hood convinces Billy to forgo police detectives, flinging a house slipper to choose their northbound direction in search of a mysterious girl who accidentally swapped suitcases at the station.

The fake moon in the pines Walking at night, Billy discovers a paper-and-lantern moon suspended in a tree and meets a girl dressed as a clown who calls herself Pierrette.

An abandoned breakfast Billy and Hood arrive for breakfast at Pierrette's bungalow, finding only a lavish spread, an artist’s studio, and a evasive companion before Pierrette disappears.

Crashing a theatrical household The travelers invite themselves to dinner at a grand estate, where Billy discovers his sister working incognito and meets the author of a popular novel titled The Madness of May.

A night in the country lockup Hood purposefully orchestrates their arrest in West Dempster to gain entry to the town jail, where Billy’s father is being held for a minor speeding infraction.

Confessions and unmaskings Inside the jail, Hood reveals his true identity as wealthy missing heir Robert Tyringham, while Billy's father admits he moved the bonds himself, clearing Billy of his supposed disaster.

The call of the road After Billy marries Roberta and the family settles into orderly life, the irrepressible Tyringham quietly steps out into the starry May night to wander once again.

The People

• Billy Deering wants to escape the catastrophic consequences of a stolen bond suitcase and avoid family disgrace; through his journey with Hood, he sheds his rigid anxiety, learns to embrace spontaneous joy, and finds love.
• Hood (Robert Tyringham) wants to live freely outside social conventions, avoid his vast inheritance, and help others rediscover happiness; he manages to secretly resolve the Deering family's crises while guiding Billy toward maturity.
• Pierrette / Roberta (Bobby) wants to play, paint, and live without the constraints of formal society; she charms Billy with her theatrical whims and eventually marries him, though she retains her love for open-air freedom.
• Mr. Deering wants to execute his duties honorably, but struggles with the immense financial temptation of managing the Tyringham estate; his odd road quest to find Tyringham leads to his arrest, but ultimately brings reconciliation with his son.
• Constance Deering (Smeraldina) wants to make her own way independently as a literary secretary while pursuing a romance with Cassowary, stepping outside her wealthy family's conventional expectations.
• Cassowary wants to faithfully serve Hood as chauffeur while maintaining his secret romance with Constance.

In Its Own Voice

"The world's roaring along at such a rate we can't find happiness anywhere but in the dictionary."

Hood explains his wandering life to Billy, arguing that modern society has traded simple joy for hurry and blood pressure.

"I live wherever I am; that's the fun of playing all the time."

Pierrette describes her carefree, nomadic view of life while sitting on a wall in her clown costume under her handmade moon.

"We depart, we skip, we are on our way, my dear boy!"

Hood rouses Billy out of his despair, urging him to leave his worries behind and embrace the open countryside.

What It's Really About

The Madness of May is a playful critique of early twentieth-century American materialism and the anxieties of corporate life. Underneath its light farce and theatrical disguises, the book asks whether modern civilization, with its rigid schedules and financial pressures, has stripped people of their capacity for spontaneous joy and laughter. Nicholson contrasts the legal and financial traps of New York banking with the restorative freedom of the open road, suggesting that true sanity often looks like madness to a hurried world. The novel argues that play, nature, and lighthearted comradeship are essential remedies for human anxiety, and that stepping outside social expectations allows individuals to fix their mistakes, heal family relationships, and discover what truly matters.

Why Read It Today

Readers who enjoy breezy, vintage romantic comedies, theatrical farces, or pastoral escapism will find The Madness of May a delightful discovery. It carries the buoyant, sunlit charm of early 1900s popular fiction, reminiscent of a stage comedy filled with eccentric characters, witty banter, and deliberate absurdities. The prose moves swiftly, celebrating springtime landscapes, starry nights, and the sheer pleasure of unscripted travel.

While the story is intentionally light and improbable, modern readers should be prepared for its unabashedly cheerful lack of realism. The plot relies heavily on coincidences, theatrical disguises, and aristocrats playing at being gypsies—elements typical of period light entertainment that require a willing suspension of disbelief. Additionally, the casual wealth of its main characters and the idealized portrayal of tramping through the countryside reflect the comfortable leisure class of 1917. Yet beneath its period flavor lies a genuinely warm, refreshing defense of taking time to sit by the roadside, pick the pebbles out of one's shoes, and laugh.