Simmons surveyed the Englemann Canyon for telegraph lines to Pikes Peak in Colorado. He was instrumental in stringing telegraph lines alongside railroads and had earlier purchased a fifty percent interest in a telegraph company. After a miserable two-day trip to the top of the mountain on a mule, he thought that there should be a more comfortable and civilized way to make the trip. He got the idea of a train from the owner of a hotel where he was staying. Simmons then financed the building of the Manitou and Pike's Peak Railway in 1889. The railway itself was built by Italian laborers and was operational by 1891. It can still be ridden to the top.