After Green Cunningham passed away on February 13, 1885, his niece and adopted daughter, Willie Permelia Bobo Montgomery, became the owner of the William S. Simmons Plantation. Willie was married to James Middleton Montgomery. At the time she acquired the property, Willie was 34 and her husband James was 41.
Willie was born March 4, 1851 in Floyd County, Georgia. Her parents were Willis Bobo and Sarah M. Cunningham Bobo (sister of Green Cunningham).[1] She was one of 12 children. Her mother Sarah died in 1852.[2]
By 1860, Willie resided with her uncle, Green Cunningham.[3]
On January 22, 1873, Willie married James Middleton Montgomery.[4]
Montgomery was the son of John Madison Montgomery and Mary Stuart Gallatin Montgomery. He was born May 31,1846 in Cave Spring, Georgia.[5]
During the Civil War, Montgomery served in Company E, 6th Georgia Cavalry.[6] There is conflicting information regarding his date of service, rank and unit assignment.[7]
James and Willie Montgomery welcomed their first child, Albert Gallatin Montgomery, in November 1873, just 10 months after their marriage. By the time Willie inherited the William S. Simmons Plantation, she and Montgomery had six children. Their seventh child, Lucile May Montgomery, was born six months after they acquired the property.[8]
Over the next nine years, the Montgomerys would add at least three more children to their family.[9]
Montgomery was active in local politics, serving at least two terms on the Cave Spring City Council, the second of which he was elected to in January 1894.[10] In April of that year, he served on the grand jury in Rome.[11]
Montgomery made the paper the following year when he visited Rome, Georgia on April 11, 1895. The article stated, “Col. J. Mid Montgomery of Cave Spring was a welcomed visitor in the Hill City today.”[12]
In 1896, an event of apparent significance took place involving a Mr. Campbell. In one of the upstairs bedrooms, next to the fireplace, someone wrote on the wall “Mr. Campbell went home July 16, 1896.”[13] No further details are available.
James Middleton Montgomery died in May of 1899, 22 days shy of his 53rd birthday. His death was reported in papers across the state. The notice stated, “J. Mid Montgomery, a prominent Cave Spring citizen, died last week of blood poison and lockjaw. Last week, he got a splinter in his finger, which resulted in his death Tuesday.”[14] He is buried in Cave Spring Cemetery in Cave Spring, Georgia.[15].
A few months later, in July 1899, the Montgomery family suffered another tragedy when John Montgomery, the nephew of John Middleton Montgomery, died at age 27 as a result of injuries sustained in a buggy accident.[16] Montgomery, described as one of the most prominent young farmers in Floyd County, was driving in a double team with a Miss Talliferro of Sandersville in Vann’s Valley when the horses “became frightened and ran at terrific speed.” Talliferro was thrown from the buggy but sustained only a few bruises. Montgomery “clung to the lines” until he was thrown over the dashboard. The article stated, “His spine was broken, his neck dislocated and his lower jaw was broken and driven back to the base of his brain.”
As of the 1900 Census, Willie Montgomery and eight of her children were still living in what was known by then as “The Montgomery House.” The census record indicates she had a total of nine living children at the time.[17] By the 1910 Census, four of her children remained at home. By 1930, only daughter, Lucille, and son, Jack (Hugh Walton Montgomery), remained in the household.[18]
In September of 1937, Lucille Montgomery bought the property. She was 52 years old.
Willie Montgomery continued living in the house until her death on October 14, 1943 at the age of 92. According to the death certificate, she died at home of heart disease.[19] She is buried at Cave Spring Cemetery.[20]
Lucille and her older brother Jack were recorded as the only occupants of the property during the 1950 Census. Lucille was listed as single and head of household. Jack was listed as single and his occupation was recorded as carpenter.[21]
Jack passed away on April 16, 1958. He was 76 years old.[22]
Lucille continued living in the house after Jack’s death and was residing there on March 5, 1963 when a tornado struck Cave Spring. Two people were injured and several Cave Spring homes were damaged during the event.[23] The tornado caused a tree to fall in the front yard of the Montgomery house, damaging the upper level of what was then a two-story covered porch.[24] The roof shingles were blown off the house, but the underlying boards were reportedly so tightly joined that the roof did not leak.[25]
Lucille Montgomery passed away in November 1967 at the age of 82. She is buried in Cave Spring Cemetery.[26]
[1]"Willie Permelia Bobo." FamilySearch, https://www.familysearch.org/en/tree/person/details/9KD5-WDV. Accessed 30 May 2025.
[2] "Find a Grave Index", FamilySearch (https://www.familysearch.org/ark:/61903/1:1:QVV8-MJKN : Thu Apr 03 02:03:01 UTC 2025), Entry for Sarah Cunningham Bobo.
[3] "United States, Census, 1860", FamilySearch (https://www.familysearch.org/ark:/61903/1:1:MZMY-FX7 : Mon Jul 08 04:38:43 UTC 2024), Entry for Green Cuninghan and Jincey Cuninghan, 1860.
[4] "Georgia, County Marriages, 1785-1950", FamilySearch (https://www.familysearch.org/ark:/61903/1:1:KXJ5-VN1 : Sun Mar 10 02:24:59 UTC 2024), Entry for J. M. Montgomery and Willa P. Bobo, 22 January 1873.
[5] "James Middleton Montgomery." FamilySearch, https://www.familysearch.org/en/tree/person/details/KZV5-NQ3. Accessed 30 May 2025.
[6] Ancestry.com. Georgia, U.S., Confederate Pension Applications, 1879-1960 [database on-line]. Provo, UT, USA: Ancestry.com Operations Inc, 2009. Original data:Confederate Pension Applications, Georgia Confederate Pension Office, RG 58-1-1, Georgia Archives. Georgia Confederate Pension Applications, Floyd, Willie P Montgomery, widow of J Mid Montgomery.Archive collection #GCP-167.
[7] There is a James M. Montgomery of Floyd County in Company E of the 8th Infantry who died during the Civil War however some of his records are attached to the Ancestry.com record for James Middleton Montgomery. The Montgomery family history site lists him as a “Bugle boy in Miller Rifles (7th Georgia Cavalry) until end of War of Northern Agression [sic].” http://www.montyhistnotes.com/genealogy/getperson.php?personID=I7750&tree=MontyHistNotes_III Accessed May 30, 2025.
[8] "Lucile May Montgomery." FamilySearch, https://www.familysearch.org/en/tree/person/details/LKG6-7VG. Accessed 30 May 2025.
[9] FamilySearch.org shows 11 children but it appears Jenny B. Montgomery and Genevieve V. Jennie Tot Montgomery are likely the same person. Ancestry.com shows 10 children.
[10] The Hustler of Rome, January 07, 1894, Image 2
[11] The Hustler of Rome, April 23, 1894, Image 2
[12] The Hustler of Rome, April 11, 1895, Image 4
[13] This is the only known instance of a message being left on the wall in the entire house. The author of the message or the exact meaning of the message is not known.
[14] Banks County Journal, June 01, 1899, Image 4
[15] Find a Grave, database and images (https://www.findagrave.com/memorial/6477672/james_middleton-montgomery: accessed May 30, 2025), memorial page for James Middleton “Mid” Montgomery (31 May 1846–9 May 1899), Find a Grave Memorial ID 6477672, citing Cave Spring Cemetery, Cave Spring, Floyd County, Georgia, USA; Maintained by Family Friend (contributor 47384645).
[16] The Morning News, July 27, 1899, Page 2, Image 2
[17] "United States, Census, 1900", FamilySearch (https://www.familysearch.org/ark:/61903/1:1:M3N2-C6Q : Thu Jan 16 11:09:50 UTC 2025), Entry for Willie Montgomery and Paul Montgomery, 1900.
[18] "United States, Census, 1930", FamilySearch (https://www.familysearch.org/ark:/61903/1:1:3MV1-TMM : Thu Jan 16 18:37:13 UTC 2025), Entry for Willey P Montgomery and Jack Montgomery, 1930.
[19] "Georgia, Deaths, 1928-1943", FamilySearch (https://www.familysearch.org/ark:/61903/1:1:QLPP-GNGC : Sat Mar 09 01:54:53 UTC 2024), Entry for Willie Bobo Montgomery and Andy Bobo, 14 October 1943.
[20] Find a Grave, database and images (https://www.findagrave.com/memorial/6477676/willie_permelia-montgomery: accessed May 30, 2025), memorial page for Willie Permelia Bobo Montgomery (4 Mar 1851–14 Oct 1943), Find a Grave Memorial ID 6477676, citing Cave Spring Cemetery, Cave Spring, Floyd County, Georgia, USA; Maintained by Family Friend (contributor 47384645).
[21] "United States, Census, 1950", FamilySearch (https://www.familysearch.org/ark:/61903/1:1:6FQ2-Z45Z : Tue Mar 19 03:17:00 UTC 2024), Entry for Lucille Montgomery and Jack W Montgomery, 6 April 1950.
[22] Find a Grave, database and images (https://www.findagrave.com/memorial/6479169/hugh_walton-montgomery: accessed June 11, 2025), memorial page for Hugh Walton “Jack” Montgomery (15 Nov 1881–16 Apr 1958), Find a Grave Memorial ID 6479169, citing Cave Spring Cemetery, Cave Spring, Floyd County, Georgia, USA; Maintained by Family Friend (contributor 47384645).
[23] Athens Banner-Herald, March 06, 1963, Home Edition, Image 1
[24] Page 20 of “Out of the Past But Still Alive” by Sibley Greer Mooney has a pen and ink drawing of what the house looked like at the time of the book’s publication in 1962. The upper level covered porch is still intact at that time.
[25] Information provided by Ina Benton Black
[26] Find a Grave, database and images (https://www.findagrave.com/memorial/6479157/lucile_may-montgomery: accessed June 4, 2025), memorial page for Lucile May Montgomery (15 Aug 1885–12 Nov 1967), Find a Grave Memorial ID 6479157, citing Cave Spring Cemetery, Cave Spring, Floyd County, Georgia, USA; Maintained by Family Friend (contributor 47384645).