The Mayor of Cumberland, Maryland is the chief executive of the government of Cumberland, as stipulated by the city Charter.
Mayors of Cumberland, Maryland (1816-present):
- (01) 1816–1823: John Scott
- (02) 1823–1824: Samuel Magill established the first newspaper in Cumberland the Allegany Freeman published weekly from 1813 to 1816 (See, Lowdermilk, page 301)
- (03) 1824–1835: Roger Perry
- (04) 1835–1836: John Gephart
- (05) 1836–1837: John Write
- (06) 1837–1838: Gustavus Beall
- (07) 1838–1839: Frederick Deems
- (08) 1839–1841: Samuel Charles
- (09) 1841–1842: James Smith
- (10) 1842–1843: John Gephart
- (11) 1843–1849: Thomas Shriver
- (12) 1849–1850: Thomas F. White
- (13) 1850–1851: Thomas Shriver
- (14) 1851–1852: Daniel Saylor
- (15) 1852–1853: John Hayes
- (16) 1853–1854: Fayette Bartholomew Tower
- (17) 1854–1855: A. L. Withers
- (18) 1855–1856: William Wallace McKaig
- (19) 1856–1857: Joseph H. Tucker
- (20) 1857–1858: James W. Jones
- (21) 1858–1860: D. W. McCleary
- (22) 1860–1861: John Humbird
- (23) 1861–1862: Charles Mynn Thruston
- (24) 1862–1863: Charles H. Ohr
- (25) 1863–1864: James Smith
- (26) 1864–1865: Charles H. Ohr
- (27) 1865–1866: George Harrison
- (28) 1866–1869: John Humbird
- (29) 1869–1871: Lloyd Lowe
- (30) 1871–1872: William Piatt
- (31) 1872–1873: John B. Widener
- (32) 1873–1874: William A. Withers
- (33) 1874–1874: William R. McCulley
- (34) 1874–1876: John Humbird
- (35) 1876–1877: William A. Withers
- (36) 1890–1890: William McMahon McKaig
- (37) 1891–1891: David J. Blackiston
- (38) 1900–1904: Warren C. White
- (39) 1904–1905: Clarence M. King
- (40) 1905–1906: William A. Cromwell
- (41) 1906–1908: Clarence M. King
- (42) 1908–1910: George A. Kean
- (43) 1910–1914: George A. Young
- (44) 1914–1932: Thomas W. Koon
- (45) 1932–1934: George Henderson
- (46) 1934–1936: George W. Legge
- (47) 1936–1939: Thomas W. Koon
- (48) 1939–1942: Harry Irvine
- (49) 1942–1944: Thomas F. Conlon
- (50) 1944–1952: Thomas S. Post
- (51) 1952–1958: Roy W. Eves
- (52) 1958–1962: J. Edwin Keech
- (53) 1962–1966: Earl D. Chaney
- (54) 1966–1974: Thomas F. Conlon, Jr.
- (55) 1974–1978: F. Perry Smith, Jr.
- (56) 1978–1982: Frank K. Nethken
- (57) 1982–1988: George M. Wyckoff, Jr.
- (58) 1988–1992: Harry Stern
- (59) 1992–2000: Edward C. Athey
- (60) 2000–2011: Lee N. Fiedler
- (61) 2011-2019: Brian K. Grim
- (62) 2019-Present: Raymond Morriss