Wendall Churchill moved to Hilton Head Island, South Carolina, with her family in 1978 at age fourteen from Chicago, Illinois. She went to Sea Pines Academy for four years of upper school. She then attended Middlebury College in New England, a liberal arts college in rural Vermont. Wendall also earned a Masters in Landscape Architecture at the University of Virginia and received her degree in 1991. After working in Baltimore, Maryland, for many years doing high-end residential projects she later moved back to Hilton Head to be closer to her mother and their beloved dog, Winston.