Hugh Calderwood was born Feb. 12, 1869, in Illinois. He came to Montana in 1899. Hugh recalls how his father, a Scotsman, told of attending the first Lincoln-Douglas debate.
Young Hugh worked with a track gang on the Great Northern west of Havre for a few days when he first came to Montana. He drifted back to Glasgow soon after, then he heard that W. W. Mabee was looking for a "hand" on his Cherry Creek Ranch. He started work, and in the ensuing years worked for several cow outfits in the area.
Many of the years were spent ranching for himself near the forks of Porcupine Creek. He served as deputy sheriff in the early 1900's.
A photograph which he calls "my 10-gallon hat picture" hangs on the walls of the Range Riders' Cafe in Miles City which has a photo gallery of many early-day eastern Montanans who truly were cowboys.
One of his experiences appears in the 1962 Diamond Jubilee edition of the Glasgow Courier as follows: "Some horses, all of them, I think, had been stolen from T. C. Power of Great Falls, former United States Senator. I picked up two horse thieves with the two horses in their possession and jailed them in Glasgow. Great Falls was notified and in a few days Curt Dennis was down to pick them up. "Puck" Powell was under-sheriff and jailer at the time. When Dennis saw the two men in custody, he turned to Powell. "That's no man," he whispered in amused astonishment, pointing to one of the horse thieves, "That's a girl." The embarrassment was everyone's since the girl had been in custody for several days as a man.
"Yes, Sir," Calderwood concluded, "I never had the slightest idea I was picking up a woman horse thief and her paramour. Of course, she was wearing a man's britches and had 'em all fooled around the jail until the man from Great Falls laid eyes on 'em".
Stories of frontier law enforcement told by Calderwood discount the tales of the "fast guns" of the early West. In an interview some years ago on the occasion of Glasgow's Diamond Jubilee, Calderwood said, "The man who went for his gun first got it first, that's all".
Some years ago when he made his home at the Red Top cabins in Glasgow he was offered a free haircut by a local barber on the occasion of his 90th birthday. The oldtimer replied, "I am waiting until I'm 100, then I'll collect it with interest, but I don't have much hair to cut."
A man who long ago turned in his lawman's badge and retired from the hurricane deck of a bronc passed the century mark. Although the pace of living has slowed over the years, Calderwood maintains a positive approach to life and remains interested in affairs of the day.