Smithsburg, MD was founded in 1813 by Christopher "Stuffle" Smith. Mr. Smith purchased a plot of land formerly known as "part of Shadrack's Lot." The community's development was directly influenced by factors such as migration paths, the arrival of the railroad, and advances in agricultural technology. By 1923, much of the existing village had been erected. Smithsburg was incorporated in 1846.

Smithsburg played a small but important role during the Civil War acting as a hospital town in 1862,treating wounded soldiers from nearby battles at South Mountain and Antietam. On July 5, 1863, Confederate General James Stuart and Union General Kilpatrick exchanged artillery fire over Smithsburg. Kilpatrick continued the advance to Boonsboro, Maryland after the engagement on July 6.

After the 3-day Battle of Gettysburg on 1-3 July 1863, General Robert E. Lee began his retreat back to Virginia on the night of July 4. Close on his trail, Kilpatrick and Custer arrived in Smithsburg around mid-day on the 5th. The town, still enjoying the previous day's 4th of July community festivities, invited the Union generals to a sumptuous meal (probably hastily gathered up picnic leftovers). First carefully placing three US artillery batteries, one each on present-day school ridge, Gardenour Hill on Water Street, and on Goat Hill ( Federal Hill today), to protect the town from surprise attack by the Confederates, the officers then sat down to enjoy their afternoon lunch.

Unsuspected by them, Jeb Stuart, screening Lee's retreating army, approached Smithsburg from Raven Rock Road and sat up his battery on Nicodemus Hill in what is now Edgemont Orchard owned by the Jacques family. A terrific artillery duel ensued, with several Rebel shells and cannonballs striking many town homes and businesses.

Realizing he was outgunned, Jeb Stuart sought to reposition his cannons. Thinking the Confederates were in the process of withdrawing, Kilpatrick broke off the engagement and moved on to Boonsboro, missing the opportunity to turn right at Cavetown and drive into Hagerstown, thus cutting into and wreaking havoc among the retreating Confederate forces. Soon after, Jeb Stuart and his troops rode through the streets of Smithsburg, turned right at Cavetown, passed through Chewsville, and reached the outskirts of Hagerstown, thereby effectively shielding Lee's army as it continued on to Williamsport and the Potomac. The Battle of Smithsburg was over.

The town of Smithsburg, Maryland is located in northeastern Washington County. Platted in 1814, the community's development was directly influenced by factors such as migration paths, the arrival of the railroad, and advances in agricultural technology. By 1923, much of the existing village had been erected. Aside from road improvements and the recent construction of suburban-type housing, Smithsburg retains its mid-19th- to early 20th-century architectural character. It is an excellent example of a community relatively untouched by modern, 20th-century architectural trends. Because Washington County has a rich collection of similar communities that appear much as they had at the turn of the century, Smithsburg's significance is important not only unto itself, but as an important contributing member to the greater architectural and cultural character of small towns in Washington County.

1845-1882 – Records not available
1882-1883 – Michael F. Sigler
1883-1886 – Daniel A. Pike
1886-1889 – Preston S. Vogel
1889-1890 – William D. Donaldson
1890-1892 – Thomas Simmers
1892-1893 – John F. Rinehart
1893-1894 – Joseph A. Wishard
1894-1895 – Lewis Reynolds
1895-1897 – Daniel J. Winter
1897-1899 – Charles F. Hoffman
1899-1900 – Thomas Simmers
1900-1901 – Walter D. Brenner
1902-1902 – W. A. Clark
1902-1903 – Samuel D. Newman
1903-1904 – John W. Ferguson
1904-1907 – Charles F. Hoffman
1905-1908 – William G. Hollingsworth
1908-1913 – John W. Ferguson
1913-1914 – Benjamin F. Carrill
1914-1921 – John W. Ferguson
1921-1922 – Samuel D. Newman
1922-1924 – J. H. Besore
1924-1925 – Louis S. Hershberger
1925-1934 – Jacob E. Brenner
1934-1948 – Charles I. Wolfinger
1948-1956 – Hoy D. Newman
1956-1974 – Stanley E. Hauver
1974-1990 – Paul Boswell
1990-1994 – John C. O'Neal
1994-1998 – Mildred (Mickey) Myers
1998-2002 – Thomas J. Bowers
2002-2018 – Mildred (Mickey) Myers
2018-2021 – Lowell (Jack) Kesselring
2021-2021 – Richard Hetherington
2021-Present – Donald L. Souders