*For a dozen years, the quiet commuter village on the Hudson was a node in an international smuggling network — and a stage for some of Prohibition's most improbable scenes*

On the evening of May 15, 1922, a Curtiss Scout biplane circled low over farmland near Croton-on-Hudson. The pilot was looking for a place to land in near-total darkness. Below him, the Albany Post Road wound through the Hudson Valley hills, and somewhere along it sat the Tumble Inn — a roadhouse that had recently attracted the attention of federal Prohibition agents. The pilot circled repeatedly, misjudged the terrain, and came down hard on a hillside owned by former Westchester County deputy sheriff George McCall.[src: 2017-11-25_the-mystery-of-the-rum-plane#cc6c22095f8a]

McCall's farm sat “about a mile and a quarter above Croton and twenty-five miles from White Plains,” facing the Albany Post Road.[src: ny_evening_world_1922_05_16#13acaa8bceb8] It was approximately a quarter-mile from the Tumble Inn. McCall rushed to the wreckage and found “a wrathful and limping man” who quickly departed in a waiting automobile before police arrived.[src: 2017-11-25_the-mystery-of-the-rum-plane#cc6c22095f8a]

State troopers from White Plains — Captain J. A. Warner and Lieutenant Roberts — found the rear cockpit packed with burlap sacks.[src: ny_evening_world_1922_05_16#13acaa8bceb8] Inside: approximately 250 quarts of Scotch and Irish whiskey, all bearing Quebec liquor commission tax stamps. “All of it, Capt. Warner said, was of excellent quality.”[src: ny_evening_world_1922_05_16#13acaa8bceb8] A Montreal newspaper from the previous day was also recovered, confirming the pilot had made the trip from Canada that same day.[src: ny_evening_world_1922_05_16#13acaa8bceb8] At bootleg prices of roughly $15 per bottle — against a Canadian purchase price of $3 — the cargo was worth approximately $3,750.

But it was the navigation chart that told the larger story. The *Evening World* described it as “about eight inches wide and thirty inches long, pasted on a heavy strip of canvas backing and rolled up so it might be carried in a pocket in the cockpit where the pilot could readily reach it. Apparently he had reached for it on many a trip.”[src: ny_evening_world_1922_05_17#3e063052f5a3] The route was “laid down in an ink line on the map, starting on a small island in the St. Lawrence River west of Montreal,” running to Glens Falls for refueling, then following the Hudson River south to Croton, where it forked: one branch toward Briarcliff and across Westchester to Stamford, Connecticut, the other south to Manhattan.[src: ny_evening_world_1922_05_17#3e063052f5a3] The chart described not a single flight but a route — an aerial smuggling corridor that had been used repeatedly.

Then there were the personal effects: a vanity box, powder puff, and “several articles of feminine attire” in the cockpit.[src: ny_evening_world_1922_05_17#3e063052f5a3]

The Man in the Naval Aviation Uniform

Two days after the crash, the *New York Evening World* published details that appeared in no other account. The article, headlined “SKY RUM RUNNER IN WOMAN'S AID IS BELIEVED NOW,” reported that “information obtained to-day indicates an attempt was made to recover this map from the wreck.”[src: ny_evening_world_1922_05_17#3e063052f5a3]

*“Among those who visited the scene yesterday was a young man in naval aviation uniform. He said he heard the machine had been abandoned and he thought there might be parts he could salvage.”*[src: ny_evening_world_1922_05_17#3e063052f5a3]

Then the critical passage:

*“According to Dr. Miller of Croton, a [naval avi]ator reached the plane soon after it crashed and called to the pilot, naming him 'Bill,' to ask what had happened. The pilot replied that his engine had 'gone back' on him. Then the pilot and the naval aviator got into an automobile and drove away.”*[src: ny_evening_world_1922_05_17#3e063052f5a3]

Two witnesses saw the same man. McCall, who discovered the wreck, never mentioned the naval aviator in his official account.[src: 2017-11-25_the-mystery-of-the-rum-plane#cc6c22095f8a] Dr. Miller of Croton told a different story — one in which a second man in a naval aviation uniform arrived immediately, addressed the pilot by name, and drove away with him. The discrepancy between McCall's silence and Miller's testimony has never been explained.

Lieutenant Roberts of the State Troopers had his own theory: he “believed, from the actions of the aviator, just before the crash, that he was expecting to meet an automobile or a truck near McCall's farm to take the liquor to one or more roadhouses on the Albany [Post Road].”[src: ny_evening_world_1922_05_16#13acaa8bceb8] Some troopers speculated more broadly: “the booze running by aeroplane was a distinctly sporting proposition of some one of the millionaire colony in Westchester,” noting that “there are many former army aviators who took a lot of chances during the war” and that such a flight “would appear to many of the former aviators as just a lark with a spice of danger to it.”[src: ny_evening_world_1922_05_16#13acaa8bceb8]

The Confession

On the same day the *Evening World* published the naval aviator detail, the *New-York Tribune* carried its own front-page story under the headline “Powder Puff Betrays Woman as Pilot of Wrecked Rum Plane.”[src: ny_tribune_1922_05_17#ed9982ff574d] The *Tribune* connected the Croton crash to a separate seizure:

*“Seizure of the airplane was almost simultaneous with capture of [a rum runner vessel] on the New Jersey coast early yesterday morning with $200,000 worth of liquors from the Bahamas. The rum runner was overhauled by the armed American rum cruiser Hahn. It was the Hahn's first capture.”*[src: ny_tribune_1922_05_17#ed9982ff574d]

A crew member from the captured vessel, whose name was withheld, made what the *Tribune* called “an extraordinary confession” to **Edward Barnes, assistant solicitor of the Collector of the Port** of New York.[src: ny_tribune_1922_05_17#ed9982ff574d] The confession directly addressed the feminine articles found in the Croton wreck:

*“This confession, it was declared last night, goes far to explain feminine toggery in the captured airplane. According to it, girls and women are regularly [engaged in rum-running between Canada and New York].”*[src: ny_tribune_1922_05_17#ed9982ff574d]

The *Tribune* then reported the confession's most remarkable detail:

*“Detailed information, including names of a score or more women rum runners, with registry numbers of planes as well as of auto trucks and marine craft engaged in the trade, are [included in a document of some] 5,000 words in length. New light on financial backing of rum traders is also given. The information is declared to be of great value to the authorities.”*[src: ny_tribune_1922_05_17#ed9982ff574d]

A score or more named women. Aircraft registry numbers. Auto truck and marine vessel identifications. Five thousand words of detailed testimony. If that confession survived — and federal customs records from the Port of New York are held at the National Archives — it would identify the pilot “Bill,” the naval aviator, and the entire smuggling ring.

The *Tribune* also noted that McCall “witnessed the crash from a distance, but before he could reach the scene an automobile picked up the pilot, who appeared injured. He was unable to distinguish the sex of the aviator.”[src: ny_tribune_1922_05_17#ed9982ff574d]

What We Know and What Remains Open

The nearest naval aviation facility in 1922 was **Naval Air Station Rockaway**, on the Rockaway Peninsula in Queens — approximately sixty miles south of Croton. Operational from 1917 to 1930, NAS Rockaway was the departure point for the first transatlantic flight (the NC-4 in 1919) and housed dozens of naval aviators in its facilities.[src: wikipedia_nas_rockaway#6c60df0583b9] A naval aviator stationed there could plausibly have driven to Croton in under two hours.

Croton itself had deep aviation connections. **Clifford B. Harmon**, the real estate developer who built the community of Harmon-on-Hudson (now part of Croton), held the sixth pilot's license issued in the United States and in 1910 became the first person to fly across Long Island Sound.[src: wikipedia_clifford_harmon#6d72cd7d112e] The Nikko Inn roadhouse, built by Harmon in 1907, stood less than two miles from the crash site. Harmon had moved to Paris by the early 1920s, but the community he built retained its connections to the aviation world.

The Smithsonian's Roger Connor, in his 2014 paper “Boardwalk Empire of the Air,” documented that aerial smuggling was “arguably the most profitable and expansive commercial enterprise in American aviation for much of the 1920s.”[src: connor_boardwalk_empire_2014#c1a7cc8b8184] Connor's research showed that by the end of Prohibition, upwards of five hundred aircraft were engaged in smuggling — at a time when only 550 aircraft were in legitimate airline service in the entire United States.[src: connor_boardwalk_empire_2014#c1a7cc8b8184] The Croton crash was not an isolated incident but one visible data point in a massive, largely undocumented industry.

The key to solving the mystery of the rum plane lies in three archival leads:

1. **The 5,000-word confession** given to Edward Barnes, Assistant Solicitor of the Collector of the Port of New York, in connection with the capture of the rum runner vessel by the cruiser Hahn on May 16, 1922. This document, if it survived, would be in **NARA Record Group 36** (Bureau of Customs, Collector of the Port of New York) or cross-filed in the Bureau of Prohibition records. 2. **The aircraft registry numbers** listed in the confession. In 1922, aircraft registration was not yet federally mandated (the Air Commerce Act came in 1926), but some states required it, and the confession explicitly names registry numbers. 3. **NAS Rockaway muster rolls** for spring 1922, available through the National Personnel Records Center in St. Louis. A search for any “William” or “Bill” in the pilot roster would narrow the field considerably.

The pilot “Bill,” the man in the naval aviation uniform, and the woman — or women — who left behind the vanity box and powder puff have never been identified. Crotonhistory.org posed the question in 2017. We have now located and extracted the primary newspaper sources that preserve the clues. The answer, if it exists, is in a customs office file cabinet in the National Archives.

The Submarines

If the rum plane represented smuggling by air, a 1924 discovery suggested the Hudson itself was being used as an underwater corridor. An aerial photograph taken by a Manhattan map-making firm captured two dark shapes in the water near Croton Point — “each approximately 250 feet long and 600 feet apart.”[src: 2014-01-04_rum-running-submarines-off-croton-point#1f345f160849]

The photograph was forwarded to the Navy, which “confirmed having no submarines in the area.”[src: 2014-01-04_rum-running-submarines-off-croton-point#1f345f160849] It was then passed to Coast Guard Intelligence and filed away. Ellen NicKenzie Lawson, in her book *Smugglers, Bootleggers and Scofflaws: Prohibition and New York City*, documented the image and placed it in context. Elsewhere in the book, Lawson recorded court testimony of a smuggler who had witnessed “a submarine appearing on Rum Row with a German captain and a French crew.” Whether the Croton Point shapes were submarines, optical artifacts, or something else entirely has never been resolved.

The Motorist's Playground

The air and the river were smuggling corridors. The roadhouses along the Albany Post Road were the retail outlets.

In the early 1920s, the stretch of road through the Croton area was marketed as part of “Westchester County, the Motorist's Playground, 900 Miles of Good Roads.” A 1921 *New-York Tribune* advertisement listed three Croton “road houses” in a single promotion. The automobile had opened the countryside to New Yorkers looking for weekend entertainment — and the Volstead Act had ensured that entertainment would involve illegal alcohol.

Three establishments formed the core of Croton's speakeasy geography. The **Tumble Inn**, situated at the location now occupied by Skyview, was opened by Captain John Jenkins and operated as a French restaurant with “an entire French staff comprising a manager, twenty waiters, a Captain, five dinner chefs, two salad chefs and five pastry chefs.”[src: 2012-04-28_tumble-inn#4014e802b8be] Actress Kay Francis held her wedding reception there; the Rockefellers, Lillian Gish, and Douglas Fairbanks Sr. were guests.[src: 2012-04-28_tumble-inn#4014e802b8be] It was also a speakeasy. The Tumble Inn was raided after a waiter handed a neatly printed wine list to a diner who happened to be **Ralph A. Day, the Federal Prohibition Director for the State of New York**.[src: 2012-04-28_tumble-inn#4014e802b8be] Federal agents arrested head waiter John J. Jenkins and waiter Joe Acerboni. Captain Jenkins refused to pay for protection as others did, and ultimately the Tumble Inn closed.[src: 2012-04-28_tumble-inn#4014e802b8be]

The **Nikko Inn**, at 80 Nordica Drive in Harmon, was built in 1907 by Clifford B. Harmon “as part of a plan to bring professional theater and film stars from New York City.” During Prohibition it became a speakeasy under the management of Roy Kojima.

Across the street, the **Mikado Inn** was built circa 1920 by “Admiral” George T. Moto — a former employee of Clifford Harmon who, following a disagreement, purchased land across from the Nikko Inn and built the competing Mikado. The rivalry between the two Japanese-themed roadhouses, operated by former colleagues, gave the Harmon intersection a character unlike anything else in Westchester.

The Undercover Fiddlers

The federal government's response to Croton's speakeasy culture was to send agents undercover — and the resulting operations had the quality of comic theater.

At the Nikko Inn, three agents embedded themselves in the evening's entertainment. The *New York Times* of June 17, 1922 reported: “McKay fiddled, Reager sang and Gallante danced.”[src: 2013-03-14_our-multi-talented-federal-prohibition-agents#8555260ad6c6] After the proprietor, Charles Hase, served them alcohol at $1.50 per drink, they arrested him and waiter Hero Gotow for violating the Volstead Act. Both received $1,000 bail.

Roy Kojima, who took over the Nikko Inn, was eventually padlocked by federal judge John C. Knox in May 1925. Years later, journalist Karl Kingsley Kitchen visited and documented Kojima's startling claim: “he asserted he had authored the popular song 'The Million-Dollar Baby' years earlier.”

The Teenage Pianist in the Cellar

At the rival Mikado Inn, the entertainment was genuine — if unconventional. In 1922, a sixteen-year-old pianist named **Oscar Levant** began performing there. In his 1965 memoir *The Memoirs of an Amnesiac*, Levant recalled that he “played the piano in a Japanese roadhouse” while sharing living quarters “with approximately twenty or thirty Japanese waiters in the cellar.”

The proprietor, nicknamed “Admiral Moto,” was “a jovial Japanese man overshadowed by his imposing Irish wife described as 'tall, dictatorial and quite respectable.'” The kitchen was managed by a twenty-year-old Italian chef from nearby Croton, trained in Japanese sukiyaki preparation. The Mikado Inn was a place where Japanese, Irish, Italian, and teenage Jewish pianists all coexisted in a ramshackle establishment that served $5 Porterhouse steaks and illegal whiskey to motorists from the city.

Admiral Moto himself had already made legal history. In 1921, he was “acquitted in what newspapers called 'the first case to be tried in Westchester County for alleged violation of the New York State liquor law.'” The acquittal set the tone: local juries had little appetite for enforcing a law the community regarded as an intrusion.

Levant would become one of America's most celebrated musicians and wits — concert pianist, actor, author, television personality. But his career began in the basement of a Croton roadhouse, sleeping on a cot next to Japanese waiters, playing for tips at a speakeasy whose owner had already beaten a liquor charge.

The Longer Pattern

The Prohibition stories are irresistible on their own terms — rum planes, possible submarines, undercover fiddlers, teenaged pianists. But they also fit a pattern that stretches back centuries. J. Thomas Scharf, in his 1886 *History of Westchester County*, charged Frederick Philipse — the colonial manor lord whose vast estate dominated the county — with “complicity with piracy, smuggling and the slave trade.” Philipse ran rum from Madagascar and traded with pirates on the same stretch of the Hudson where, 250 years later, Curtiss biplanes would crash-land with Canadian whiskey.

The geography explains the continuity. The Hudson River has always been a corridor between Canada and New York, and the Croton area — with its sheltered cove, its proximity to both the river and the overland roads, its distance from the city but accessibility to it — has always been a natural waypoint for anyone moving goods that authority did not want moved. The Kitchawank traded on this river. The Dutch smuggled on it. The cowboys and skinners of the Revolution plundered along it. And the bootleggers of the 1920s, with their biplanes and their submarines and their fiddling federal agents, were simply the latest in a long line of people who understood that the fastest way between Montreal and Manhattan ran right through Croton.

Sources

**Primary newspaper sources (newly extracted from Library of Congress, April 2026):** - *The Evening World* (New York, N.Y.), May 16, 1922, p. 5. “Hooch Airplane Captured by State Troopers.” LOC Chronicling America: sn83030193. Full OCR text ingested into history.croton.news corpus. - *The Evening World* (New York, N.Y.), May 17, 1922, p. 15. “Sky Rum Runner in Woman's Aid Is Believed Now.” LOC Chronicling America: sn83030193. Full OCR text ingested. - *New-York Tribune*, May 17, 1922, p. 9. “Powder Puff Betrays Woman as Pilot of Wrecked Rum Plane.” LOC Chronicling America: sn83030214. Full OCR text ingested.

**Secondary sources:** - “The Mystery of the Rum Plane,” crotonhistory.org (2017) - “Another Mystery of the Rum Plane,” crotonhistory.org (2018) - “Rum-Running Submarines off Croton Point,” crotonhistory.org - “Tumble Inn,” crotonhistory.org - Lawson, Ellen NicKenzie. *Smugglers, Bootleggers and Scofflaws: Prohibition and New York City* (2013) - Connor, Roger Douglas. “Boardwalk Empire of the Air: Aerial Bootlegging in Prohibition Era America.” Smithsonian National Air and Space Museum (2014). - “Oscar Levant Plays the Mikado,” crotonhistory.org - “Our Multi-Talented Federal Prohibition Agents,” crotonhistory.org - Scharf, J. Thomas. *History of Westchester County* (1886) - *New York Times*, May 16, 1922; June 17, 1922