Dorthy “Dot” Gwaltney was born on August 30, 1933 to Marguerite Walden and Stanley Lane Gwaltney. Dot was a beloved and involved member of the Windsor community as shown through her 60+ years of volunteer experience with organizations such as The Windsor Homemakers, Suffolk Meals on Wheels, Friends of the Windsor Library, and more. In particular, Dot was a dedicated member of the Woman’s Club of Windsor where she was a keystone member and club president twice. Isle of Wight County’s Farm Day was also an important event to her, and for years she shared decades of knowledge about farming and nature with countless children. Dot was also famous for her recipe notebook complete with amounts for purchasing and cooking large meals. Her hobbies included reading, sewing, quilting (for which she had a great talent), scrapbooking, and travel. Beyond her philanthropy, Dot is also well known for having been the matriarch of Windsor’s Indika Farms where she joined her husband William, who had been growing peanuts, in starting a peanut-buying business in 1956. The business grew substantially and Dot continued to help even after the family business was passed on to her sons by assisting with the books and weighing the peanut trucks. Throughout everything, Dot was a dedicated member of the Windsor Congregational Christian Church and expressed her deep and abiding faith. 

Regena F. Johnson was born on April 2, 1911, to Beatrice and Henry A. Fix in Shenandoah, Virginia. As a child, she loved music and played violin and piano among other instruments. She was even drum major in the Shenandoah High School Band. Her talent in music led her to graduate from the Cincinnati Conservatory of Music with a Bachelor of Music degree and to attend the University of Cincinnati where she majored in voice. After graduation, Regena came to Isle of Wight in 1933 and was the first music teacher at Cypress Chapel High School near Suffolk where she taught for 7 years. She married Dunston Johnson in 1941 after meeting on a blind date and moved to Windsor where she taught music again until 1988 when she retired. Following her husband’s death not long after her retirement, Regena traveled from coast to coast in the US as well as to Australia, New Zealand, Hawaii, and Alaska. During her life in Windsor Regena was a member of many organizations and an integral part of the community. Beyond being a member of the Virginia Music Teachers Association, the Music Teachers National Association, the National Guild of Piano Teachers, and the Tidewater Music Teachers Forum, she served as president and vice president of the Woman’s Club of Windsor, president of the Southside District of the Virginia Federation of Women’s Clubs, and advisor to the Junior Woman’s Club. Regena was a deaconess as well as the choir director and pianist at Windsor Baptist Church for 47 years, was the town’s Girl Scout leader, a Worthy Matron of Sinai Chapter #18 of the Order of the Eastern Star, and a member of Delta Kappa Gamma. She is quoted as saying she only regretted never learning to pilot an airplane. 

Maggie Walker was born free on July 15, 1864, to Elizabeth Draper, a freed slave, and Eccles Cuthbert, an Irish immigrant, Confederate soldier, and journalist at the New York Herald. The nature of her parents' relationship is unknown, but not long after her birth, her mother married William Mitchell. When Maggie was nine years old, her stepfather died, the details of which are debated. Officially, his death was ruled a suicide, but the family believed him to have been murdered. It was her stepfather’s death that plunged the family into poverty and drove Maggie’s mother to start a small laundry business, which Maggie assisted with. This job first exposed her to the economic and social disparities between races at that time. 

Growing up, Maggie attended one of the newly established schools for African Americans in Richmond. She went to the Lancasterian School, followed by the Navy Hill School, and finally the Richmond Colored Normal School, where she trained to be a teacher. Upon graduation in 1883, she returned to the Lancasterian School where she taught for three years. While working as a teacher, she also took part-time employment as an insurance agent with the Woman’s Union and attended night classes in accounting. Notably, the Woman’s Union worked to help meet the needs of Richmond’s African American community.  In 1886, she was forced to quit after marrying Armstead Walker, Jr as school policy forbade the employment of married women. 

During her schooling, Maggie joined the local council of the Independent Order of St. Luke, a fraternal organization established as a burial society. The order ministered to the sick and aged, promoted humanitarian causes, provided long-term economic and social support during the post-slavery period, and is known to have shaped African American identity. Her experiences with the order further exposed her to racial disparity. After being forced to leave her teaching position, Maggie devoted herself to the order and quickly rose through its ranks, eventually reaching the top leadership position of Right Worthy Grand Secretary. While in this position, she saved the order from financial ruin at the hands of the former Right Worthy Grand Secretary William Forrester and greatly expanded the order’s size and influence. She maintained this position until she died in 1934. While holding the position of Deputy Matron in 1895, before she assumed order leadership, she founded the Juvenile Branch of the Independent Order of Saint Luke with the goal of establishing a sense of community consciousness and confidence in young African Americans. 

Together, Armstead and Maggie had three sons, two of whom made it to adulthood, and an adopted daughter. They purchased a family home at 110 1/2 East Leigh Street, located in what was dubbed Richmond’s “Harlem of the South”. This home became a family hub and at one point, housed numerous generations concurrently. Tragically, one of her sons, Russell, accidentally killed Armstead in 1915 after mistaking him for a burglar. Thankfully, Maggie’s work and investments kept the family afloat. 

In 1902, Maggie first published The St. Luke Herald to spread the Independent Order of St. Luke’s message. The publication was known to have railed against mob lynchings and Jim Crow policies, and helped to organize streetcar protests against segregation half a century before Montgomery’s boycotts. In 1903 she established the St. Luke Penny Savings Bank, being the first woman of any race to charter a bank in the United States. The goal of the bank was to help finance African American home ownership, and she served as the bank’s first president. Maggie voraciously urged young African Americans to open bank accounts early so their money would grow as they did, and they’d start their adult lives with more financial independence. She also opened the Saint Luke Emporium in 1905 to offer African American women employment opportunities and the African American community access to cheaper goods. White businessmen offered Miaggie $10,000 to cancel her emporium plans which she rejected. While the St. Luke Penny Savings Bank remained operational and African American-owned until 2009 (albeit under a different name post mergers during The Great Depression), the Emporium sadly closed in 1911.

Maggie was also known to have loved entertaining and frequently invited African American leaders to dine at her home. Notable guests include W.E.B Du Bois, Langston Huges, and Mary McLeod Bethune. Further, she established and maintained a Comunity House in Richmond, helped to staff and advise the Piedmont Sanitorium, handled funds for the National League of Republican Colored Women, particapted in women’s suffrage and voter registration campaigns, helped form the Virginia Lily-Black Republican party, and unsuccesfully ran for Virginia’s superintendent of public instruction. Other organizations she served included the Council of Colored Women, NAACP Richmond Branch, Negro Organization Society, NAACP, National Urban League, Virginia Interracial Committee, State Federation of Colored Women, International Council of Women of the Darker Races, National Association of Wage Earners, and the National Association of Colored Women’s Clubs among others.

In 1907, Maggie fell, damaging the nerves and tendons in her knees, rendering her mostly homebound for the last decades of her life. Due to diabetes, her wounds never quite healed, and by 1928 she was wheelchair-bound. She passed away on December 15, 1934 from diabetes gangrene and was buried at Richmond’s Evergreen Cemetery. 

There is so much more to know about Maggie Walker’s life and her legacy to detail it all here. Please research her if you have the time. 

Carita “Rita” Richardson was born to Walter and Rena Jones in Volney, a small town in southwestern Virginia. Her family, including beloved younger brother Jerry, had a strong connection to the mountainous area, having settled there generations before. Rita had a strong church community that she attributes to her growth. She also excelled at school and knew from a young age she would be a teacher, following in her grandmother's and mother’s footsteps. After graduating as valedictorian from Independence High School in 1967, she went on to graduate with honors from Radford College in 1970 after double majoring in math and Spanish. During her college years, she met a Virginia Tech student named Bentley Richardson who graduated a year before her and took a teaching job in the small town of Windsor, Virginia. After graduating, Rita married Bentley and joined him in Windsor, becoming a high school math teacher.

Rita remained at Windsor High for the next 30 years, having a long and storied career. Beyond teaching math classes, she started the Spanish department and proceeded to teach thousands of students both subjects. She was beloved by her students and was even selected by the student body as Teacher of the Year in 1978. She was also frequently selected by students to be featured in Whose Who Among America’s Teachers. Rita retired in 2002 due to a deteriorating back issue and dedicated herself to taking care of her health. 

It was in 2005 that Bentley asked her to accompany him to a Town Council meeting. During this meeting, the next year’s proposed budget was being discussed, and Rita was aghast that the largest area of the budget was a lump sum with no line items to show how it was to be spent. After unsuccessful attempts to talk with the then-mayor, as well as failed attempts to convince other community members to run for council, she took it upon herself to run in 2006 and secured a seat against all odds. She proceeded to serve as a council member for four years and then as Mayor for eight and a half years. 

During her tenure as mayor, Rita had a hand in numerous town improvements, including the development of new monetary policies enabling the town to save millions of dollars without raising the then $0.10 tax rate, designing and installing new, brick town entrance signs, purchasing and renovating a building for the town’s first police station, purchasing 5 acres adjacent to said police station to be used for future municipal building projects, working with the Windsor Girl Scouts to paint a historical mural showing the town’s history (which won a prestigious award given by the Hampton Roads Art League), and working with the Board of Supervisors and School Board to renovate the 14,000 square foot gym complex that became the Windosr Town Center. 

Rita claims her greatest reward is “being able to live in this wonderful town with fantastic people who continue to thank me for the things I tried to do to make our town a better place to live”. In addition to that reward, however, she received the Plan Virginia award from the state in 2012 and was presented, along with her council, House Resolution #100 by the General Assembly in 2013. In her own words, “As a quiet, shy 20-year-old who came to a town she had never heard of to become a teacher like she had always wanted to be, I would have run screaming back to the mountains if I had been told I would become the Mayor of Windsor!!! I never expected that turn my life took, but I have loved it all, just as I love the town and people of Windsor!!!”. 

Coming soon