The town was the headquarters for the Yellowstone Division that encompassed 875 route miles (1,408 km); 546 (879) in main line and 328 (528) in branches with the main routes from Mandan, North Dakota, to Billings, Montana, and from Billings to Livingston.

The town of Glendive is an agricultural and ranching hub of eastern Montana sited between the Yellowstone River and the Badlands.

[3] Sir George Gore, a wealthy Irish sportsman, named the local tributary to the Yellowstone River in his favorite hunting area "Glendive" in 1855.

Glendive was established by the Northern Pacific Railway during the building of the railroad line.

[5][6] The settlement mainly consisted of tents and log cabins until a building boom ensued with the arrival of first load of lumber in 1881.

[6] In January 2015, Glendive was the site of a major oil spill from a pipeline which also contaminated drinking water.

[8] On October 24, 2023, a fire destroyed the Jordan Inn and the Rose Theater,[9] both located in the Merrill Avenue Historic District.

[12] Glendive experiences a semi-arid climate (Köppen BSk) with long, cold, dry winters and hot, wetter summers.

Moving the oil out of the area was difficult and expensive though; the boom ended by 1954 and only a small reserve existed locally.

The community has been impacted in the 2000s by the North Dakota oil boom which spurred a modest increase in the population.

[19] Dawson County High School's team name is the Red Devils.

[23] The Glendive market has three local radio stations: Glendive is the smallest of the 210 designated markets for broadcast television in the United States as designated by Nielsen Media Research,[24] with one station—KXGN channel 5—carrying a CBS affiliation along with state and local news broadcasts for a small potential audience of several thousand people (county population is 9,059).

In late June 2010, KXGN moved their NBC programming to a DT2 digital subchannel, rejoining the network.