• October 2 – A Polish uprising against the Nazis in Warsaw ended after 68 days, leaving 200,000 civilians dead and much of the city ruined. A staff sergeant of the 7th Ferrying Group was stabbed to death near Fort Benton, suicide suspected.
• October 9 – Six were charged in the murder of Billings resident Frederick Kembel.
• October 11 – Two German POWs escaped from a farm near Hathaway.
• October 20 – Senator and vice-presidential candidate Harry Truman spoke in Butte. U.S. troops landed on the Philippine island of Leyte.
• October 23 – Two German POWs escaped from the Sidney camp. One was believed to be wearing women’s clothing after performing in a play.
• October 26 – The Montana Education Association met in Helena.
• October 28 – Prison inmates and Warm Springs patients helped the Forest Service put out a 90-acre fire near the Deer Lodge racetrack.
• October 29 – Pheasant season opened.
Read more about October 1944 in Montana