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