R
- Ramsdell, Homer, Erie 1853–1857.
- Ramsey, Joseph, Jr., WAB 1901-1905, WM 1903-1908.
- Rea, Samuel, PRR 1913–1925, LIRR 1923-1928.
- Redfearn, Donald D. (born 1953), RailAmerica.
- Reed, James H., P&LE 1892-1896.
- Reed, John Shedd (1917–2008), ATSF 1967–1986.
- Reid, Robert Gillespie (1842–1908), NFRy 1889-1908.
- Reidy, Edward T. (born 1903), CGW 1957-1968.
- Reinhart, Joseph, ATSF 1893–1894.
- Reistrup, Paul, Amtrak.
- Rice, Richard D., MEC 1870-1873.
- Rice, W. Thomas (1913–2006), RFP 1955-1957, ACL 1957-1967, SCL 1967-, CSX.
- Rich, Walter (1946–2007), NYSW 1980-.
- Riddle, Hugh (1822–1892), RI 1877-1883.
- Rión, Francisco Javier, TFM 2005–present.
- Ripley, Edward Payson, ATSF 1896–1920.
- Ritchie, Robert J., CPR 1990-2005.
- Roberson, Bob, FWWR
- Roberts, George B., PRR 1880–1896.
- Rogers, Henry H. (1840–1909), VGN.
- Ronan, William J., NYMTA.
- Ropes, David N., LIRR 1876-1877.
- Rose, Matthew K. (born 1960), BNSF 1999–present.
- Ross, Walter L. (born 1852), NKP 1929-.
- Rouvillois, Philippe, SNCF -1986.
- Rowland, Ross, Pacific Wilderness Railway 2000-2001.
- Roy, Jon R., IAIS -2002.
- Russell, Donald, SP 1952-1972.
- Rutter, James H., NYC 1883-1885.
Read more about this topic: List Of Railroad Executives