One of the happiest days in the Gallatin Basin, long before it became the Big Sky Resort, was quite possibly the day in June 1949 when Emmett Crail married his long-time sweetheart, Anaconda school teacher Annie Breneman.
Annie Breneman was born in 1886 in Montana, the daughter of David and Annie Breneman. She trained as a school teacher, and taught in the Anaconda school district.
How Annie and Emmett met, we do not know.
And finally, marriage...
Emmett was a legendary procrastinator, and he and Annie did not marry until 1949, when Emmett was 61 and Annie was 63.
This picture is thought to be the wedding picture of Emmett and Annie Crail. Crail Ranch docents today delight in noting Emmett's "deer in the headlights" look, as though after three decades he still felt that he was rushed into things....
Emmett Crail was born in Bozeman in 1887, the second child of Augustus Franklin and Sallie Creek Crail.
After his father died in September, 1924, Emmett took over the Ranch and continued to raise cattle and wheat. He seemed to enjoy his solitary ranching life, and he remained a bachelor for many years.
Tragedy befell Annie's family in November, 1918 when Annie's brother, Duburg Breneman, and his wife, Rilla, died within a few days of each other of Spanish Flu, leaving their three children orphans.
The youngest child, just an infant, was adopted by a family from Anaconda. However, the task of raising the two older children, -- a boy named David, age 5, and a girl named Glen Louise, age 2 -- fell to Annie.
Annie and her nephew and niece were frequent visitors to the Crail Ranch during the 1920s and 1930s.
< Here Emmett pals around with David and Glen Louise Breneman. This picture is hand-titled "The Bunch" in the collection given to Historic Crail Ranch by the Crail family.
Annie and Emmett lived together on the Crail Ranch for just a short time. In 1950, again for reasons on which we can only speculate, they decided to sell the Crail Ranch and move to Bozeman.
Sadly, their married life together was fairly short. Annie died in 1958 and is interred in the Bozeman cemetery.
After the last visit to Crail Ranch, young Frank Crail took his father Eugene, his aunt Lilian and his uncle Emmett to live with him on his ranch in Salem Oregon.
Lilian died in there in 1981 and Eugene died there in 1985, but Emmett Crail stayed in Oregon for only a few years. In the early months of 1975, feeling that his days were growing short, he returned to Montana to be once again with Annie's niece and nephew.
Emmett Crail died in June of 1975, at the age of 86. He is buried near his wife, Annie, in the Breneman plot in the Bozeman cemetery.

By 1970, Lilian and Emmett had lost their spouses. In that summer, Frank Crail, son of Eugene Crail, brought Eugene and Emmett back up the old road to Crail Ranch, which was then being used to house workers building the Big Sky Resort.
Carole Crail, wife of young Frank Crail, took a picture of Emmett, Eugene and his wife Alice, along with Frank and children outside the main cabin.
As far as is known, this is the last time any of the original homestead children saw the Crail Ranch.
But that is not quite the end of the love story of Emmett and Annie....
Now: Download an expanded version of the love story of Emmett and Annie.