Walt heard of a Skyway system being tested in Switzerland in the fall of 1955, and naturally had to have one. By November of 1955, Walt figured out where the ride would go, and had the Von Roll Iron Works engineers work with designer John Hench to create the attraction. Walt purchased a used 1947 Type 101 Sidechair #5, which was one of the Von Roll prototypes.

Opening ceremonies were presided over by Walt himself and Dr. Walter Smidt, the Swiss Consul General of Los Angeles. There were 42 round gondolas that could carry 2 guests at a time, seated in fiberglass patio chairs bolted into the floor. Moving at a slow and steady 4 mph, gondolas were dispatched approximately every 9 seconds.

The Skyway gave guests an overview of the park between two stations: one in Fantasyland (where the drive system was located) and the other in Tomorrowland (where 35,000 pounds of ballast kept the 2400' long cables taut). In between was the peak, a support tower located on Holiday Hill (basically a mound of dirt).

In 1959, the Matterhorn was added in the path of the Skyway, complete with 2 holes for the gondolas to pass through. The original round buckets were replaced in 1965 for the Tencennial Celebration. Each bucket was now able to carry four guests. The grips on the cars also changed; the original 10 sheave rollerbatteries and the entire tower in Tomorrowland were removed. During the Fantasyland remodel, the towers there were beefed up with extra supports at the urging of Von Roll Tramways.

On April 17, 1994, a 30 year old man jumped from the Skyway, landing in a tree, relatively unharmed. The Skyway was removed 7 months later in November, partially because it was too costly to make safety upgrades. People also threw objects and spit at guests below as they went overhead. For the final ride, Mickey & Minnie made the last crossing as guests watched below.  When the Skyway closed, the holes in the Matterhorn were filled in and the supports were dismantled within weeks.

Another reason it closed was because the ride was in technical violation of the Americans With Disabilities Act. It was very difficult to load and unload mobility-impaired guests (guests had to step up when boarding and down when de-boarding), and this usually required having to stop the ride. Furthermore, wheelchairs could not be loaded onboard because the vehicles were too small. Approximately 150 million guests rode the Skyway.

The Disneyland railroad sweeper train makes one last circle tour only picking up park guests on the way, then everyone disembarks at the Main Street station. This train leaves at closing.

Sweeper trains are based on the number of order of which trains come out on the line on a particular day. The first train out on the line in the morning is usually the first train off the line for the night. The second train follows out soon after the first train when coming out on the line for the day, but stays out for a longer time about 30 minutes prior to part closing.

The last train to come out for the day is usually the last train put away for the night. That is the train that normally sweeps. The train departs Main Street around midnight and returns between 12:15 - 12:30 depending on the engine pulling the train and depending on how busy the stations actually are.

FUN FACTS
Attraction type: straddle-beam Monorail
Designer: WED Enterprises
Height: 41 ft
Speed: 30 mph
Vehicle type: Monorail Trains
Vehicles: 3
Riders per vehicle: 120
Duration: 11 minutes
Vehicle names:  Monorail Red, Monorail Blue, Monorail Orange
Track gauge:  Single straddle-beam