The trails from Jordan's fort to Humphreys' ford on the Big Muddy River intersected the old trail from Lusk's ferry at modern-day Golconda to Kaskaskia, which was first settled by French colonists.

[4] Isaac Herring entered the first land in what became Herrin on 4 November 1816, two years before Illinois became a state.

At the time he lived to the west in Jackson County, the land entry was the northeast quarter off Section 30, Township 8 South, Range 2 East of the Third Principal Meridian.

During the Civil War, he built a frame store building and secured a fourth class post office that opened on May 26, 1864.

After coal was discovered and mining began in nearby Carterville, Harrison, and his cousins Ephraim Snyder Herrin and Mrs. Williams in 1892 prospected for coal beginning at the southwest corner of Williams' farm, identified in 1939 as the corner of Legion Boulevard and East Herrin Street.

Cousins Harrison and Herrin, great-grandsons of Isaac Herring, made plans for a new town.

The Dorsey Brothers and Frank Sinatra played bocce ball and performed there.

Three future presidents came to Herrin during campaigns: Richard Nixon, John F. Kennedy and Ronald Reagan.

In the beginning of the 21st century, Herrin by coincidence experienced two total eclipses of the sun in just seven years - the first on August 21st, 2017, and the second on April 8th, 2024.

On the 17th of July 2015 mayors Steve Frattini and Flavio Polloni signed the Twinning Proclamation Act to officially declare Herrin and Cuggiono as sister cities.

Herrin hosts the annual HerrinFesta Italiana, a Memorial Day weekend celebration of the town's Italian heritage.

The five-day event often draws over 60,000 people for live music, authentic Italian food, a carnival, Bocce Ball tournament, and "Bigga Nose" and pasta-eating contests, as well as many other activities.