It is generally accepted that the name of Calabasas is derived from the Spanish calabaza meaning “pumpkin”, “squash”, or “gourd”. Calabasas history shows that the Chumash Indians once called this place their home. At the top of Calabasas grade east of Las Virgenes on the original El Camino Real legend is that in 1824 a Basque rancher from Oxnard spilled a wagon-load of pumpkins on the road en route to Los Angeles. The following spring, hundreds of pumpkin seeds sprouted alongside the road. The area was named Las Calabasas – the place where the pumpkins fell.

In honor of its namesake Calabasas holds an annual Pumpkin Festival in October, including carnival games, exhibits, demonstrations, and live entertainment. Pumpkin Festival is held at Juan Bautista de Anza Park in Calabasas.

To one side of Calabasas is Las Virgenes Open Space at 2,983 acres lined with miles and miles of scenic hiking and horseback riding trails and to the opposite on the west are the Santa Monica Mountains which is preserved as the Santa Monica Mountains National Recreation Area boasting 156,670 acres rich with trails, streams and wildlife. The Santa Monica Mountains also is most famous as the backdrop for the film and television series M.A.S.H. Which still hold relics of the show including the famous directional sign of cities both near and far.