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Remembering Herndon’s History: The Caywoods of Herndon


Benjamin and Philena Caywood were prominent Herndon citizens who settled here before Herndon became an incorporated town, leaving a long Herndon legacy.

Benjamin Caywood (1812-1891) and Philena Waring Caywood (1817-1892), were both born in New York. They are believed to have been married in the 1830s and would ultimately have nine children: Ann Maria, Charlotte, Louisa, Sarah, Aaron, Luther, Lauretta, Emma and Charles.

In 1849, the Caywoods and their five oldest children relocated to Herndon, Virginia. It is believed that this movement south was due to the California Gold Rush. Benjamin had learned that many Virginians flocked westward in search of riches, causing the price of land in Virginia to be depressed. Benjamin used this opportunity to invest in local land at bargain prices.

Caywood siblings with spouses and children, 1897. (Benjamin C. Garrett, II).

In 1853 Benjamin purchased 200 acres of land for $1,116 on the west side of Fairfax County, much of which is now part of the Town of Herndon. This land is now the area generally surrounded by Elden Street, Sterling Road, Route 28 and Herndon Parkway. Their home was located on south Elden Street near the present day intersection of Herndon Parkway. Mr. Caywood farmed the land, cultivating fruit trees, specializing in peaches. In 1861 the Caywoods sold 100 acres of their land to Job C. Champlin for $2,000.

Mr. Caywood’s contributed to some of Herndon’s important beginnings. Caywood’s very laudatory obituary said, “He ran the first road through from Drainsville to Little River pike,” although that statement is unproven. Such a connecting roadway, that cud include what is now Elden Street, would have been very advantageous during this time period in the mid to late-1850s when the Alexandria, Loudoun and Hampshire Railroad was being built through Herndon.”

It was also in the 1850s that Methodism was coming about in Herndon. Former Herndon resident Lottie Dyer Schneider (1879-1967) wrote in her memoir “Memories of Herndon, Virginia” that Methodist families were scattered about in the area in 1857-58 and they formed a Methodist congregation. The Caywoods were one of those families. However, the Civil War interrupted further work on the construction of a church, which would not come until later. Lottie said that the Herndon Methodist church records started in 1867 and “protracted meetings were held at Mr. Caywood’s.”

The Civil War period (1861-1865) was difficult for the Caywoods. Many people in the small yet-to-be-named village of Herndon had split loyalties. The Caywoods and their children remained loyal to the Union, sometimes causing the family to be fearful during the war

One Sunday, Kathryn “Kitty” Kitchen Hanna (1830-1907), a Herndon resident and southern sympathizer, described in an interview how she could hear the big guns firing at Manassas. Her cousin Jim White told her how it was the Southerners firing. Later Kitty met the Caywoods and Mrs. Caywood asked her, “Kitty, is there any news?” 

“No news,” Kitty answered, “but I know the Southerns has whipped.” 

“How’s that?” Mrs. Caywood said, turning pale, for the Caywoods
were Northerners.

“I know ‘cause the big gun’s comin’ nearer this way, an’ it must be the Southerns
has won.” 

And that is how it turned out. At one point, after the First Battle of Manassas in 1861, Benjamin Caywood was arrested and held briefly by the Confederates. 

According to Lottie Dyer Schneider – who lived in Herndon from 1879 to 1920 – President Lincoln sent a carriage for the Caywood family to bring them into Washington when Confederate activity in the area made him fear for their safety. The Caywoods stayed in Washington throughout the war. It is unknown how the President knew of the Caywoods or their difficult situation, living as Unionists in Virginia. 

After the war, the Caywoods moved back to their home in Herndon. Their Herndon farm was heavily damaged as a result of the war. Union sympathizers who had lived in the Southern states during the Civil War were able to apply for reimbursements for property losses. In 1872, the Southern Claims Commission approved the Caywood’s claim for damages, resulting in $972 in compensation. 

Not too long after the war, Mr. Caywood helped get the Town’s public school started on Center Street. Caywood, as well as four other Herndon citizens, were noted as trustees in the 1869 deed of sale for the land on which the school was built. Some of his grandchildren would later attend that school. 

By 1870 the need for a church building was recognized by the Herndon Methodist congregation. In 1872 Daniel and Maria Calyer sold one acre of land to Benjamin Caywood and six other Herndon men who were acting as trustees of the Methodist Episcopal Church of Herndon. This lot was located at the northwest corner of Elden and Center Streets. The church was built soon thereafter. Emma Caywood’s name was found on the roll of the first Bible class. 

After the war, at some point in the 1870s, the Caywoods moved back to Washington. Mr. Caywood worked in the real estate business with his son, Aaron. As early as 1865 an IRS tax assessment record listed Benjamin Caywood’s occupation as real estate agent. In 1872 the Caywoods sold the remaining half of their Herndon land – 100 acres – to a Washingtonian, Mrs. Julia Liesman, for $7,000. 

Some of the Caywood children remained in Herndon and became well-known citizens themselves. Ann Maria Caywood married widower, John P. Raub, who, like Benjamin, was also an early trustee of the Herndon School and Herndon’s Methodist Church. The Raubs owned land nearby the Caywoods. They had no children.

Charlotte Caywood married Civil War veteran James W. Corey. He purchased land on Lynn Street and was the person who, in 1869, initially started building what is now the Nachman building (The Green Lizard Cycling shop). 

Prior to getting married, Louisa Caywood attended the play “Our American Cousin” at Ford’s Theatre the night President Lincoln was assassinated. According to a Caywood family genealogy document, “The Caywoods of Herndon, Virginia,” written by Benjamin Caywood Garrett, II, Louisa’s brother Aaron placed Louisa on his shoulder in order to help her escape the theatre during the panic. Soon after, Louisa married Enos Garrett. Their house was located at the southeast corner of Elden and Center Streets, catty-corner from the Methodist Church, where he would become the Secretary of the Sunday School. Enos was a wheelwright and blacksmith by trade who later became the Mayor of Herndon. 

Sarah Caywood married James Madison Whipple and they eventually lived in the well-known Yellow House in Herndon, formerly located on Elden Street at the present location of the Adams-Green funeral home. The house has since been relocated to the corner of Oak and Pearl Streets. Madison briefly served as Herndon’s postmaster. 

Aaron Caywood remained in Washington after the Civil War and went into the real estate and rental business. He initially ran his business out of the Caywood home at 1632 16th Street, N.W., Washington, D.C. Later he also had a branch office in Herndon. He married Aurilla Stevens, a New Hampshire native, and they stayed in Washington. 

Luther was the first Caywood child born in Herndon, however, he died in 1854 at the age of four. 

Like Luther, Lauretta Caywood and her younger two siblings were born in Herndon. After the war she returned to Herndon with her parents. She never married and would later return to Washington with her parents after 1870, staying with them until their deaths. In the 1890s she bought lots 12, 13 and 14 in Herndon’s Eldenwood Fruit Farm subdivision, the area now between Spruce and School Streets. She sold these lots in 1910. At the time of her own death in 1943, she was the last of the Caywood siblings still living. 

After returning to Herndon with her parents at the conclusion of the Civil War, Emma Caywood married John Pfouts Garrett, a nephew of Enos Garrett, who had been living with his parents on a Loudoun County farm. John and Emma both worked for brother Aaron Caywood in the real estate business. They resided in Washington for the rest of their lives. 

The last Caywood child, Charles, attended school in Washington when the family evacuated there during the war. He became a sales clerk, got married and later worked with his brother Aaron in the real estate business. He and his wife, Carrie Frazier, stayed in Washington. 

Some of the extended Caywood family continued to have an impact in Herndon, especially the Garretts who lived in Herndon for the majority of their lives. Enos Garrett’s brother, Henry Hipple Garrett, also served as a Herndon Mayor. Yet another Garrett brother, Benjamin, was elected to the Herndon Town Council. Many of the Garrett children went to Herndon schools. Most of the boys went into the lumber business.

After returning to Washington, Benjamin and Philena remained there for the rest of their lives. In 1890 the Caywood farm in Herndon was acquired by Levi Jacob Groh who operated it as a dairy farm. Benjamin died in 1891 followed by Phelina’s death in 1892. They are both buried in Washington’s Rock Creek Cemetery. In his will, Benjamin Caywood left all his real estate and personal property to Philena and Lauretta, respectively. Lauretta had acted as a family caretaker for much of her life. 

John and Ann Maria Caywood Raub, and Enos and Louisa Caywood Garrett, (and many other members of the Garrett family) are buried in Herndon’s Chestnut Grove Cemetery. 

Eventually the Caywood home that used to be located on the west side of south
Elden Street was torn down to make way for new stores. 

About this column: “Remembering Herndon’s History” is a regular Herndon Patch feature offering stories and anecdotes about Herndon’s past. The articles are written by members of the Herndon Historical Society. Barbara Glakas is a member. A complete list of “Remembering Herndon’s History” columns is available on the Historical Society website at

The Herndon Historical Society operates a small museum that focuses on local history. It is housed in the Herndon Depot in downtown Herndon on Lynn Street and is open every Sunday from noon until 3:00. Visit the Society’s website at, and the Historical Society’s Facebook page at… for more information.

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