Harriet Leonora Straw was born May 3, 1824, in Wytheville, Va., and educated at the Moravian School in Salem, N.C. She was 19 in April 1843, when she came to Chattanooga to teach music to the daughter of recently widowed Col. James A. Whiteside. She married him Feb. 1, 1844, becoming the stepmother of his five children and the wife of one of Chattanooga's wealthiest citizens.
Attorney Tomlinson Fort described her as "highly educated, a splendid conversationalist, queenly in her style, capable of fulfilling any station in life to which she might be called, and with it all she was a beautiful woman."
Between 1845 and 1859 she bore nine children.
Col. Whiteside purchased most of the north end of Lookout Mountain in Tennessee and christened the spring beneath the eastern bluff "Leonora Spring" in his wife's honor. In February 1852, he incorporated the Lookout Mountain Turnpike Co. and installed a toll road called the Whiteside Turnpike to the Point, where he built a public hotel and 25 cottages that opened for business June 1, 1858.
Ardent secessionists, the Whitesides probably approved the decision of their 16-year-old son James to join Company B of the Rock City Guards, 1st Tennessee Infantry, in April of 1861. Late that summer when James became ill in Virginia, his father went to bring him home.
Already ailing, Col. Whiteside never recovered from the trip and died Nov. 12, 1861. He left a fortune in land, railroad stock and mines. His 36-year-old wife received a child's share with each of the children from both marriages and was executor of his estate.
She barely managed to put her husband's affairs in order before Confederates under Gen. Braxton Bragg occupied Chattanooga. When Union troops were besieged there in the fall of 1863, she boarded a few Union officers but refused to move out of her house or give them her rosewood piano. Although she had taken the oath of allegiance, in the spring of 1864 Gen. William T. Sherman deported her and her seven children to Springfield, Ohio.
When Lincoln was assassinated in April of 1865, hers was the only house in town not draped in mourning. A mob descended on her house, but the organist of the neighboring church came to the rescue and used her black alpaca underskirt to drape the front entrance.
In fall 1865, she returned to Chattanooga to find her house full of Union officers. After one of the children came down with chicken pox, she posted a sign reading "small pox," and they quickly moved out.
For the next 20 years, she fought to re-establish control over and ownership of all that had been lost or taken during the war with the help of Chattanooga's best lawyers.
Among newcomers to the city was Varney A. Gaskill, a handsome Vermont native who was practicing law in Chattanooga. Harriet Whiteside married him in the mid-1870s.
When a new stock company formed to build a rival toll road called the St. Elmo Pike up Lookout Mountain, Gaskill represented his wife in the courts. He lost the lawsuit, and his wife sued for divorce.
After a bitter fight, the divorce was granted on July 17, 1879, and Gaskill was ordered to pay costs.
Thus began what The Chattanooga Times titled "The War of the Mountain Roads." When the rival toll road was completed, she charged those using the St. Elmo Pike a fee to gain access to the Point. Then a land company formed to lay cable tracks up the mountain from St. Elmo to a site below the Point, where a new hotel was built.
In 1887, Harriet Whiteside sold her Lookout Mountain property but continued to fight for control of the tourist trade by financing Incline No. 2 in 1895.
The war ended three years later when the U.S. government purchased the property and incorporated the Point into the national military park.
Harriet Whiteside died on Feb. 1, 1903, but the controversy that surrounded her in life lived on. Three of her sons contested the will leaving her estate to her two daughters and 13 grandchildren. It was finally settled out of court.
Her former attorney, W.G M. Thomas testified: "She was the best informed woman I ever had any dealings with and the best business woman I ever knew. She was remarkably successful."
She was both ahead of her time and a law unto herself.
Kay Baker Gaston is a regional historian and former Chattanoogan. For more, visit Chattahistoricalassoc.org.