On May 15, 1922, a Curtis biplane crashed on a farm near Croton-on-Hudson, New York, carrying a cargo of illegal liquor during the Prohibition era. The incident has come to be known as "The Mystery of the Rum Plane."

The Crash

As darkness fell, the aircraft circled over farmland owned by former Westchester County deputy sheriff George McCall, located approximately a mile above Croton and a quarter-mile from the Tumble Inn roadhouse. The pilot initially hesitated to land, circling repeatedly before deciding to descend. Flying at roughly 1,000 feet in near-total darkness, the pilot misjudged the terrain and came down hard on a hillside. The impact caused the plane's nose to dig into the earth, crumpling the wings and ruptured fuel tank.

McCall rushed to the wreckage and detected the distinctive odor of whiskey amid the smell of gasoline and oil. Rather than finding a dead pilot, he discovered "a wrathful and limping man" who quickly departed in a waiting automobile before police arrived.

The Cargo

State troopers from White Plains discovered the plane's rear cockpit packed with burlap sacks containing approximately 250 quarts of Scotch and Irish whiskey, all bearing Quebec liquor commission tax stamps. Many bottles remained intact despite the crash. At the time, bootleg whiskey sold for roughly $15 per bottle in New York, suggesting the cargo's value approached $3,750—representing substantial profit given the $3 Canadian purchase price.

The Route Map

A worn navigation chart found in the wreckage revealed the pilot's intended route. The map traced a path from Montreal to Glens Falls, New York, then followed the Hudson River to Croton, where it forked into two branches: one running toward Briarcliff and Connecticut, and another extending south toward Manhattan. This evidence suggested an active aerial smuggling operation supplying wealthy Westchester County residents and New York speakeasies.

The Powder Puff Pilot Theory

Items discovered aboard the plane—including "a vanity box, powder puff and several articles of feminine attire"—sparked speculation about the pilot's identity and gender. A confession from rum runners captured near New Jersey two days after the crash added credence to theories that women regularly participated in aerial smuggling operations between Montreal and New York.

The Croton Connection

The crash site's proximity to the Tumble Inn, a notorious speakeasy, raised questions about coordination. Weeks earlier, Federal Prohibition Director Ralph A. Day had led agents in raiding the inn after receiving a wine list from its waiter. Additional raids on the Nikko Inn and questions surrounding "Admiral" George T. Moto's nearby Mikado Inn suggested intensive enforcement activity in the area.

Unanswered Questions

A mysterious figure in a naval aviator's uniform reportedly arrived at the crash scene shortly after the plane went down, calling out to the pilot by name. According to Dr. Miller of Croton, this man and the pilot subsequently departed together in an automobile—a detail absent from McCall's official account. The aviator's identity and purpose remain unknown, adding another layer to the incident's lingering mysteries.