Jennie came over Independence Pass into Aspen in the early 1880's with her husband, John S. Adair, She always claimed that shows the first woman to travel in a covered wagon down the torturous old trail called "that Abomination" by the Aspen Times. Jennie and her husband ran a logging and sawmill operation above Aspen in Widow's Gulch up in Hunter Creek, a beautiful hanging U-shaped valley carved by an ancient glacier. The gulch was named for Jennie after her husband died as she continued their business, lifting her own logs and driving her own teams and lumber wagons down the steep and dangerous road to town. Cover the years she also ran several boarding houses, one near the sawmill in Hunter Creek and one in Aspen on 7th Street. At one time she also pastured dairy cows on Pitkin Green, selling their milk, and teams of horses which she rented. She had no children.

Jennie is remembered by the old timers as a small, feminine woman with a magnificent head of curly hair (white in later years), and physically as strong as any man. Her determination matched her strength and she gave as good as she got from the men in the often cutthroat logging business, letting them fell and attempt to steal logs from her, but retrieving them at the point of a shotgun as the men tried to remove them from her property. She was a good cook, having fed so many miners and loggers—and she used to put a whole side of beef in the oven, slicing off the outside portions as they were done and then pushing the beef further into the oven to get more of it cooked. She wore men's clothing—a shocking thing to do in those days—in order to do all that heavy work and to avoid accidents with long skirts around the wagons and sawmill equipment. To keep it safe, she may have hidden her money in a well as she is remembered to have sometimes paid with wet money-for work done. She also did embroidery and painted dishes; she loved flowers and built a greenhouse on the side of her home.

In the late 1890’s, as silver mining declined and there was less demand for lumber; Jennie moved her sawmill down to Aspen on some land she owned in the Lakeview Addition at the junction of Hunter Creek and the Roaring Fork River. She continued to support herself until she became too old.

Heaven may protect the working girl, but it didn’t then, as it doesn't now, protect the old woman who is no longer able to care for herself. Her house fell into disrepair, and Jennie, like others of Aspen's old people, found herself visiting friends and not leaving until she was given some food to take home. When she died on July 4, 1937, at the age of eighty-six and after six weeks in the hospital, she still owned and was living on the same property with her small frame house, a few cows and steers, arid her sawmill shed and equipment. Her Lakeview property had a chattel mortgage on it and back taxes were owed-on it and other small land holdings. She had a few shares in the Midnight Mining Company which brought in a little money, but other investments were worthless. When her estate was settled there was nothing left to pay the administrator and she was buried in a still unmarked grave in her lot in Red Butte Cemetery.

Jennie was a rare woman, staying in Aspen after her husband's death and doing a man's work in a man's world. Most widows stayed only a few years, operating boarding houses and then remarrying or leaving Aspen to go back to their original homes and families. Jennie was too much in love with Hunter Creek and Aspen to leave, and she was too independent to remarry.

In 1975, Aspen's City Council honored Jennie by setting aside, as Jennie Adair Sawmill Park, part of her former property down around the settling pond near Hunter Creek and the Roaring Fork.