MASSEY — Massey Aerodrome and Massey Air Museum held a “fly-out” on Sunday, Oct. 26 to commemorate the 100th anniversary of Jimmy Doolittle’s victory in the Schneider Trophy race held on Oct. 26, 1925.
Eleven aircraft flew to the Chesapeake Bay from Massey to retrace one 31-mile-long triangular lap of the original race course.
Jimmy Doolittle is most known for leading the 1942 raid on Japan only five months after Pearl Harbor, for which he received the Medal of Honor. Sixteen B-25 bombers took off from the aircraft carrier USS Hornet to deliver the first blow to the Japanese mainland in World War II.
But Doolittle also was a pioneering aviator who established many speed and distance records, and won numerous air races — the most prestigious being the Schneider Trophy race held on the Chesapeake Bay at Baltimore.
The planes from Massey entered the course below Rock Hall, flew to North Point Park, around the Baltimore Harbor Lighthouse and back to the Rock Hall turn to complete one lap.
Well-known vintage Warbird owner Larry Kelley of Georgetown, Delaware flew with Robert Masone in Masone’s 1940 Waco biplane.
Kelley was the most prominent organizer of the Doolittle Raiders Reunions held annually until the last of the 80 original crew members, Doolittle’s co-pilot Lt. Col. Richard Cole, died in 2019.
Kelley displays his B-25 bomber “Panchito” at air shows around the country and did so at the Doolittle Raiders Reunions.
He is the “custodian” of one of Jimmy Doolittle’s proud possessions, a Longines “Lindbergh Hour Angle” wristwatch inscribed “Jim From Mother 1939.”
Kelley loaned the watch to Masone for this year’s flight saying, “Of course I brought Jimmy Doolittle’s wristwatch for Bob to wear as he retraced that famous race route 100 years after Doolittle.”
Printed here is a list of aircraft and pilots who attended the Oct. 26, 2025 event.
N115DL 1961 Beech BE-95; John Caputo of Chestertown
NC164 1940 Waco UPF-7; Robert J. Masone of Milton, Delaware
N24787 2001 Cessna 172S; Navy Annapolis Flight Center Inc., Edgewater, Frank Kennedy and Jennifer Wong
N352RV Vans RV-12; Dan Wroe of Denton
N36AA 1978 Bonanza A36; Ralph Portnoy of California (Maryland)
N4443K 1948 Ryan Navion; Rick Clark of Royal Oak
N48110 1952 de Havilland DHC-1; Rusty Lowry of Leonardtown [based at Massey]
N734DY 1977 Cessna 172N; George Mohr of Ewing, New Jersey
N75NM 1944 Stearman; Nick Mirales of Prince Frederick [based at Massey]
N7574J 1968 Piper PA-28R-180 Arrow; David Baden of Mechanicsville
N81RG 1949 Stampe SV-4; Edwin Remsberg of Fallston
