Born in Harpers Ferry, West Virginia, Cutshaw studied engineering at the Virginia Military Institute, graduating in 1858. The Colonel, a veteran of the Confederate Army, returned to the institute to practice civil engineering and teach mathematics, physics, and civil and military engineering while he recovered from the loss of his leg during the Civil War. He was appointed Richmond City Engineer in 1873, in part the result of a letter of recommendation penned by Robert E. Lee.
Cutshaw was responsible for Richmond’s public works, city buildings, and civic grounds during Reconstruction. A tireless advocate for the public realm, he studied larger East Coast and European cities for inspiration in park design and architecture. He provided Richmond with its first public parks and squares, a park system master plan, and tree-lined streets and boulevards. Committed to urban forestry, Cutshaw established a city tree nursery that yielded 50,000 trees during his tenure. His landscape contributions reflect his interest in the City Beautiful movement and include Picturesque parks, grand avenues, monuments, and curvilinear carriage drives. He was interred at Hollywood Cemetery in Richmond upon his death.