1000 Mile Challenge

Maybe you’d love to bike Across America, but you can’t get away for long enough this summer. Maybe you could handle one of our Moderate treks, but you want to push yourself a little. Or maybe you’d love to see Chicago, New York, and the whole stretch of America between them. This exhilarating 30-day bike trip is designed for you.

Cycle just over 1,000 miles on a varied route through rolling farm country, alongside the Great Lakes and Niagara Falls, and through bustling cities. Starting in the Midwest, you’ll leave Chicago and cruise through Illinois, Indiana, Ohio, a smidgen of Pennsylvania, and New York state. In Cleveland, you’ll visit the Rock and Roll Hall of Fame, and you’ll stop for chicken wings in Buffalo, the city where they were invented. Visit Niagara Falls, then start your descent through beautiful upstate New York, and ride along the Hudson into Manhattan, where the trek ends.

Apply now to bike the 1000 Mile Challenge!

Trek Highlights

  • Visit Chicago, Ft. Wayne, Toledo, Cleveland, Buffalo, New York (and everything in between)
  • See the Great Lakes, the Rock and Roll Hall of Fame, Niagara Falls, and Manhattan
  • Bike 60 – 85 miles/day
  • Camp out and stay in hostels and hotels

Trek Details

Starts: Chicago, IL

Ends: New York, NY

Cost: $3595 – 30 Days

Biking:  CHALLENGING (Approximate Daily Mileage 60 – 85)


10-12+ June 21 – July 20   

10-12+ July 5 – Aug 3