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Episode 103 is the thirty-eighth episode of the second season of Where in Time is Carmen Sandiego?


Sir Vile steals the wilderness road from Kentucky in 1775.

At the time of the crime, Kevin and the time pilots get clues from Sir Vile, who, after taunting them as "lily-liver'd time twerps," directs them to 1838, when the Cherokee were being sent down the Trail of Tears, and they give Global Pursuit.

After Global Pursuit through the 1830s, Kevin welcomes aboard a happy model-T driver who gives clues directing them to the 1920s, when Route 66 first opened, before Sir Vile sabotages the Chronoskimmer.

In a parallel universe, the evil Kevin and Comisar seek the 'good' Carmen in the 1970s, when the Oregon Trail computer game was first incorporated into schools. In our universe, Kevin and the time pilots follow Sir Vile there and retrieve the Wilderness Road.

Ben captures Sir Vile and Carmen Sandiego with 6 seconds to spare.

Time Pilots[]

  • Gina Gilroy
  • Ben Silverman
  • Allison

Sketches and Pit Stops[]

  • VILE Villain Clue - 1838 (during the Trail of Tears)
  • Global Pursuit
  • Cluefinder (motorist) - 1920s (when Route 66 was formed)
  • Data Boost
  • Parallel Universe - 1970s (when the Oregon Trail computer game was first developed)

History of Trails and Migrations (Flight Plan)[]

  • 1996: The first time pilot runs the "Trail of Time" on Where in Time is Carmen Sandiego?
  • 1957: Jack Kerouac's novel On the Road is first published.
  • 1942: The Alaska Highway is built during World War II.
  • 1904: The first automobile speed limits are passed in New York.
  • 1849: Harriet Tubman escapes slavery via the Underground Railroad.
  • 1838: The Cherokee are forced to march on the Trail of Tears.
  • 1789: The first known U.S. road maps are published.
  • 1775: Daniel Boone blazes the Wilderness Road.

Trail of Time Questions[]

Bold indicates correct answers.
Italics indicates contestant's answers.
Underline indicates the contestant answered the question after time ran out.

  1. It's 1542. What highway is begun by the Spanish in California?
    • La Baja
    • El Camino Real
  2. It's 1838. What discovery on Cherokee land leads to the forced march on the Trail of Tears?
    • Oil
    • Gold
  3. It's the 1870s. To where are cowboys leading cattle on trail drives?
    • Train stations
    • Sea ports
  4. It's 1921. What does forester Benton MacKaye propose for hikers?
    • Appalachian Trail
    • Trail rescue code
  5. It's 1968. What does the US Congress establish?
    • National Trail System
    • National Park Service
  6. It's 1973. How long does it take to win the first complete Iditarod sled dog race?
    • 10 days
    • 20 days



  • The happy Model-T driver first appeared in the 34th episode of the first season.
  • This episode reveals that Sir Vile dislikes the injustice of the Trail of Tears.
  • The only 1 wrong answer Ben got on the trail of time was the pendulum wheel contraption at the 5th portal.
  • Sir Vile assaulted the chronoskimmer by pressing button numbers at the chronoksimmer hatch and breathed fire at it and said, “Thy mechanical beast is no match for Sir Vile!” and laughed evilly.

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