I wonder how the rich figured out how to get permission for specific times to use their cars on the railroads. Hmm, well, I suppose they met at parties and talked to the railroad owners, or the golf course.

Glidden made his fortune in the telephone industry before retiring in 1901. He was the millionaire sponsor of the Glidden Reliability Tours from 1905 to 1913.

 His 1902 circumnavigation of the globe with his wife Lucy and a "Motor Engineer" Charles Thomas covered over 48,000 miles, showcasing the endurance of early automobiles. 

His Napier was with flanged wheels to operate on railroads, as those were the only roads across most countries that carried the wealthy in comfort, from city to city, vs small country towns with no luxury hotels

Mr. and Mrs. Charles J. Glidden drove this 24hp Napier automobile during several notable journeys, in 1904 they completed the first crossing of the Canadian Rockies by automobile, arriving in Vancouver, Canada, after a 3,536-mile trip from Boston, Massachusetts. 

This journey was part of the AAA Glidden Tour, a reliability run that aimed to prove the viability of automobiles for long-distance travel. The couple had previously participated in the 1904 St. Louis Tour, where they arrived in Albany, New York.

The couple’s 24hp Napier was a symbol of early automotive exploration and reliability testing, and their journeys helped establish the automobile as a practical tool for travel and commerce.

Mr and Mrs Charles J Glidden in 24hp Napier which they toured for 8 years, beginning in 1901, covering over 46000 miles, here travelling on rails with a railway official.

https://forums.aaca.org/topic/341211-period-images-to-relieve-some-of-the-stress/page/389/

I'd forgotten that I'd posted these two magazine clippings in 2019, http://justacarguy.blogspot.com/2019/04/this-is-first-ive-learned-that-glidden.html

Glidden's professional career began at the age of 15. At 20, he was Branch Manager for the Atlantic and Pacific Telegraph Company.

 He recognized early the potential of the phone together and experimented together with Alexander Graham Bell with telephone connections over the telegraph lines. 

Glidden funded the construction of telephone lines in Manchester, New Hampshire and was the first to recognize that the female voice was more suitable for the early telephones than the male. Accordingly, he hired women as telephone operators. 

The telephone exchange, which he had initiated, grew to a syndicate, which, amongst others, covered the U.S. states of Ohio, Minnesota, Arkansas, and Texas. The first long-distance telephone connection (from Lowell, Massachusetts to Boston) was established on his initiative.

In 1901, he sold his company to Bell and hit the road for adventure, with a successful trip to the Arctic Circle. 

He and his wife Lucy, stopped into all the major cities of the world, seen here in London in 1902

In 1902, his world tour took him over 46,528 miles through 39 countries and ultimately around the world twice.

The Glidden Tour trophy originally sported a sterling silver 1901 Napier automobile perched atop the porcelain enameled globe. That priceless little objet d'art vanished long ago.

 

The 1911 "Anderson, South Carolina Perpetual Automobile Touring Trophy" also known as, "The Anderson Trophy" was presented to AAA by the citizens of Anderson, SC to be awarded perpetually to the individual winner of the Glidden Tours, and was first won by the Governor of Georgia, who was chauffeured on the 1911 Glidden Tour in his 1912 Maxwell. The tour ran from New York City to Jacksonville, FL covering 1,460 miles on the then-new National Highway.

Anderson was visited by the 1909 and 1910 Good Roads Tour, (New York Herald and Atlanta Journal) the 1911 Glidden Tour, and the 1912 Army Road Test. 7 decades later, Bosch, BMW, and Michelin USA would take residence there, as well as the ICAR, Clemson University International Center for Automotive Research

For an example of what a luxury tour it was to be a part of, read https://steamboatminnehaha.org/the-glidden-tour-of-1909/ which goes into detail of how the wealthy on tour were treated to all the best each city on the tour had to offer, such as in Minneapolis.

The contestants were treated like celebrities with streetcar rides to Minnehaha Falls and spent the afternoon at Fort Snelling, where military troops met them with a full-out dress parade, including mounted cavalry and artillery men. A reception was held shortly after at the Officer’s Club before the party moved on to an afternoon horse race featuring World Champion pacer Dan Patch.

the Glidden contestants enjoyed Sunday at the Tonka Bay Hotel on Lake Minnetonka. The TCRT excursion boats Plymouth and Puritan were hired for the afternoon to give tours of the lake before the drivers retired to the Lake Minnetonka Automobile Country Club for drinks and dinner.

From 1905 to 1910, Glidden was the first president of the Aero Club of America. From 1908, he began to promote aviation. He praised the lighter than air technology (balloon flight) and was of the opinion that private planes would be similarly ubiquitous as motorcycles.

https://en.wikipedia.org/wiki/Charles_Jasper_Glidden

https://steamboatminnehaha.org/the-glidden-tour-of-1909/

https://robtnar.wordpress.com/2011/09/19/1911-glidden-pathfinder-flanders-20-down-the-dixie-trail-new-york-to-jacksonville-the-studebaker-corporation-e-m-f-companies-factories-detroit-michigan/

For dozens more photos of the Gliddens on their many years of explorations, see https://digitalcollections.detroitpubliclibrary.org/islandora/search?f%5B0%5D=mods_subject_topic_ms%3A%22Glidden%2C%20Charles%20J.%20%28Charles%20Jasper%29%2C%201857-1927%22