1,000 Mile Challenge

Trek Overview

Trek Description

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.

Trek Highlights

Trek Details

Why Choose 1,000 Mile Challenge

Experiencing Great Lakes Cities


The 1,000 Mile Challenge starts in Chicago and winds through Great Lake cities like Toledo, Cleveland and Buffalo, finally finishing in New York City. Each major Great Lake city is a day-off for trekkers to explore museums like the Rock and Roll Hall of Fame and iconic landmarks like Niagara Falls. The route travels past two of the Great Lakes, Lake Michigan and Lake Erie experiencing the bustling cities and farmlands in-between.

Lasting Friendships


Twenty-five days together with a traveling pod of like-minded adventurers creates lasting bonds and formidable memories for years to come. This trip is challenging as the team must keep up high daily mileage while maintaining their bikes, cooking nutritious meals and navigating across the Midwest and Northeast. The team must work together and be a helpful member of the group to complete the 1,000 Miles in 25 days. By the time they reach NYC, they will have experienced many highs and lows that will bond them and leave a shared sense of accomplishment.

America Up-Close


If you want a challenging adventure crossing many U.S. states but don't have the summer availability to complete the Across America Trek, the 1,000 Mile Challenge is the perfect fit. You will cross 5 States from the Midwest to the East Coast, accomplishing more than 50 miles daily. While a condensed version of the Across America Trek, this trip is a significant length to leave you feeling accomplished and tightly bonded to fellow trekkers. You will celebrate in New York City over pizza and likely feel the confidence to take on Across America next!

Get in Touch

to learn more about the 1,000 Mile Challenge

Call or email us to inquire about trek availability or to answer any questions about bike touring adventures with Teen Treks.