- Hackworth, Timothy (1786-1850) - Pioneering English steam locomotive designer and builder.
- Hallidie, Andrew Smith (1836-1900) - Developed the first practical cable car system for San Francisco, California.
- Hamberger, Edward R. - President of the Association of American Railroads.
- Hanna, David Blyth (1858-1938) - First president of Canadian National Railway.
- Hannaford, Jule Murat (1850-1934) - President of Northern Pacific Railway 1913-1920.
- Harbeson, John (1888-1986) - Architect and industrial designer who helped with the design of the Pioneer Zephyr in 1934 and Denver Zephyr in 1936.
- Harnden, William F. (1812-1845) - Began career as a ticket salesman for the Boston & Providence Railroad, became the first person to send an express shipment by rail in 1839 and founded Harnden & Company as a result of this experience.
- Harris, Robert (born 1830) - President of Chicago, Burlington & Quincy Railroad 1876-1878; president of Northern Pacific Railway 1884-1888.
- Harrison, George M. - President of the Brotherhood of Railway and Steamship Clerks.
- Harvey, Fred (1835-1901) - Entrepreneur who developed the Harvey House chain of restaurants in conjunction with the Santa Fe Railroad.
- Haswell, John (1812-1897) - Scottish locomotive builder; became prominent with locomotive construction in Austria, building the first six-coupled locomotive for that country.
- Havemeyer, Henry Osborne (1847-1907) - President of Long Island Rail Road 1875-1876.
- Haverty, Michael R. (born 1944) - President of Santa Fe Railroad 1989-1995; president of Kansas City Southern Railway 1995-present; Railroader of the Year 2001.
- Hayes, Charles - President of Southern Pacific Railroad 1900-__.
- Hedley, William (1773-1843) - Pioneering English locomotive designer and builder of Puffing Billy in cooperation with Timothy Hackworth.
- Henszey, William P. - Mechanical superintendent at Baldwin Locomotive Works in the 1870s. (White, 1973, p 6)
- Heywood, T. E. - Chief Mechanical Engineer for Great North of Scotland Railway 1914-1922.
- Hill, A. J. - Chief Mechanical Engineer for Great Eastern Railway 1912-1922.
- Hill, James J. (1838-1916) - President of Great Northern Railway and Northern Pacific Railway.
- Hoke, Robert (1837-1912) - Director for North Carolina Railroad after the American Civil War.
- Holden, J. - Chief Mechanical Engineer for Great Eastern Railway 1885-1907.
- Holden, S. D. - Chief Mechanical Engineer for Great Eastern Railway 1908-1912.
- Holliday, Cyrus K. (1826-1900) - First president of Atchison, Topeka & Santa Fe Railroad 1860-1863.
- Holmes, M. - Chief Mechanical Engineer for North British Railway 1882-1903.
- Hone, Philip (1780-1851) - First president of Delaware & Hudson Railway 1825-1826.
- Hoon, Geoff - British Secretary of State for Transport.
- Hopkins, Mark (1813-1878) - A member of The Big Four group of financiers in California.
- Howard, Nathaniel Lamson (1887-1949) - Worked for Chicago, Burlington & Quincy Railroad and Chicago Union Station Company; president of Chicago Great Western Railway 1925-1929.
- Hudson, George (1800-1871) - English railway financier known as "The Railway King."
- Huggins, Larry A. - Director for Metra 1997-present; Treasurer for Metra 2006-2009; Vice-chairman of the board for Metra 2009-present.
- Hughes, David - Interim President of Amtrak 2005-2006.
- Hughes, George (1865-1945) - Chief Mechanical Engineer for the Lancashire & Yorkshire Railway 1904–1922, the London & North Western Railway 1922–1923 and the London, Midland & Scottish Railway 1925–1931.
- Huntington, Collis Potter (1821-1900) - A member of the Big Four group of financiers in California.
- Huntington, Henry Edward (1850-1927) - Nephew of Collis P. Huntington; executive in charge of Pacific Electric Railway in the early 20th century.
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