In 1903 a Horatio Nelson Jackson, an eccentric doctor from Vermont, makes a $50 bet that he can be the first person to drive an automobile coast to coast in under 90 days. Despite not even owning a car, having no driving experience, and no road maps to plan the route Jackson heads out within five days of making the wager. The story was first written in the book, Horatio's Drive: America's first road trip, by Dayton Duncan, who would later unite with documentary film maker Ken Burns to create a feature PBS documentary film.

Highlights from the show include:

• What makes a really good road trip?

• Road tripping basics

• Dayton earliest road trip memory

• Dayton's first impression of Ken Burns

• The Brooklyn Bridge film

• The most unusual $50 wager at a California social club

• Discovering Horatio Nelson Jackson

• Settling on the Winton touring car

• The start of the 1903 trip in San Francisco

• Documenting the trip

• Picking up a 4 legged passenger along the Route

• What happens when Jackson asked for directions

• Copy cats attempting to cross the continent by auto

• • Packard Company attempt

  • Oldsmobile attempt

• Winton Car Company asks Jackson to allow sponsorship

• Jackson turns down any financial help

• Jackson arrives into NYC under his own terms

• Packard and Oldsmobile final results

• Life after the historic ride

• Working alongside Ken Burns

• Artifacts at The Smithsonian Museum

Thank you to Route 66 Podcast supporters, including:

• Rob and Cheryl Cochran – Maryland
• Jim Crabtree – California
• Todd Farrell – Nebraska
• John Garza - Texas
• Rich Havlik – Minnesota
• Mary Nicholson – Pennsylvania
• Phil Norton - Pennsylvania
• Mark Wilson – Texas

And from the United Kingdom

• Charli Beeton

THE MOTHER ROAD AT 100: The Voices of Route 66

A multimedia presentation featuring Route 66 before, during, and after its heyday

During the centennial year of Route 66 schedule a virtual or in person presentation by Route 66 Podcast host, Anthony Arno, highlighting episodes over the past 10 years. An optional trivia option is available, where all attendees can participate to win Route 66 related prizes- either virtually or in person!

Click HERE for more information

The Chain of Rocks Bridge was an active Route 66 passage over the Mississippi River between 1936 - 1966. Although no longer open to vehicular traffic, the Chain of Rocks Bridge allows visitors to walk a 1 mile authentic stretch of Route 66 across the Mississippi.

Join Route 66 Podcast host Anthony Arno as he talks tih Elizabeth Simmons, from the Great Rivers Greenway about the popularity and almost complete demise of the Chain of Rocks bridge.

Highlights from this episode include:

• The Great Rivers Greenway Mission

• Earliest bridges to cross the Mississippi River

• Physical location of Chain of Rocks Bridge

• 1936 Route 66 alignment on Chain of Rocks Bridge

• Peak bridge years with amusement park

• Commercial barge traffic on Mississippi River

• Namesake of Chain of Rocks

• Chain of Rocks channel

• Chouteau Island

• Construction of 1953 canal on east side

• Castle like structures at Chain of Rock Bridge

• Physical dimensions and unusual bend on Chain of Rocks Bridge

• Gretchen (bridge keeper volunteer)

  • Earliest memory of Chain of Rocks Bridge

  • Involvement as an ambassador at Chain of Rocks Bridge

  • Typical bridge keeper duties

  • Personal connection to bridge

  • Most memorable people on the bridge

  • Wildlife sightings on Mississippi

  • Most recent renovations on the bridge

1970 - 1999

• Bridge closed to the public and slated for demolition

• What ironically saved the Chain of Rocks Bridge from demolition

• Reopening as a pedestrian bridge in 1999 with Trialnet

• Great Rivers Greenway established in 2000

• Future options for Chain of Rocks Bridge

• Activities and events at Chain of Rocks Bridge

• Other Green Rivers Greenway destinations

Remembering Connie Echols

The Route 66 Podcast pays a special tribute to Connie Echols, who passed away on May 2, 2026, at the age of 76 years old. The Wagon Wheel Motel is the longest, continuously operated motel along Route 66.

The Route 66 Podcast pays a special tribute to Connie Echols, who passed away on May 2, 2026, at the age of 76 years old.

This episode was originally released in 2018 as Connie was nearing her 10th anniversary of owning and operating The Wagon Wheel Motel.

Join host Anthony Arno as he talks with Connie about:

Website: The Wagon Wheel Motel

Website: Wagon Wheel Facebook Page

Connie Echols, owner Wagon Wheel Motel

Show highlights:

• Connie's other profession before purchasing The Wagon Wheel Motel
• Early history of The Wagon Wheel Motel
• Most popular items sold at The Wagon Wheel Gift Shop
• Why the original motel garages were removed from adjoining rooms
• The original Wagon Wheel Neon sign and why there's only one sign facing east, and no sign facing travelers as they travel west
• Keeping in touch with other historic Route 66 Motels
• Latest projects at The Wagon Wheel that Connie is working on
• Local area attractions for Cuba, MO
• Annual events in the area
• Famous guests who stayed at The Wagon Wheel Motel