Last updated June 7, 2026

Event for 2027 has not been confirmed yet… The Cheaha Challenge Gran Fondo 2027, now in its 31st year, takes off annually from Jacksonville, Alabama, and is one of America’s top cycling events, if not Alabama’s. Picked by Strambecco as one of the Best Road Cycling Events in the Southeast, this ride is exceptional for every level of rider, and no rider ability from amateur to world tour pro is left out. The Cheaha Challenge Gran Fondo 2027 is a partner event in the prestigious Gran Fondo National Series and a qualifier event for the USA Cycling Gran Fondo National Championship. The event is also a UCI Gran Fondo World Series event and a qualifier for the UCI Gran Fondo World Championship. Route options start at a 12-mile cruise and go all the way up to the “big ones,” the popular GFNS and UCI qualifying century with nearly 10,000 ft. of climbing, and the Ultra, an astonishing 126.3-mile route with just under 13,000 feet of climbing! Some of the distances offer the chance to ride up Mount Cheaha, the highest point in the state of Alabama.

The event was started in 1993 by Mike Vickers, the past president of the Northeast Alabama Bicycle Club. Vickers envisioned a challenging bike ride from Piedmont down Highway 9 up the scenic drive over Cheaha Mountain to Adam’s Gap and back. The event is now the largest century ride in Alabama and attracts cyclists from around the world.

The Cheaha Challenge Gran Fondo features six routes, each with its own difficulty level and elevation profile. The ULTRA covers 126 miles and 13,385 feet of climbing, following the same course as the 100-mile route but adding a loop around the Talladega National Forest and the Dugger Mountain Wilderness Area. The 100 Mile Challenge covers 100 miles and 9,714 feet of climbing, starting and finishing on the campus of Jacksonville State University and passing through the towns of Piedmont, Heflin, and Delta. Riders face challenging climbs including White’s Gap, Heflin Mountain, Horseblock, Not Again, OH SHIFT!, Adam’s Gap, and the iconic ascent of Mount Cheaha. This route is a UCI qualifying distance, meaning that the top 25% of finishers in each age group will earn a spot for the UCI Gran Fondo World Championships. The 84 Mile Challenge covers 84 miles and 7,958 feet of climbing and is also a UCI qualifying distance for riders aged 55 and above.

In addition to the Gran Fondo, the event features a time trial on Saturday. The time trial is a 12-mile race against the clock on a closed course with only three turns, all near the finish. The time trial starts in Piedmont and finishes in Jacksonville and is also a UCI qualifying event, with the top three finishers in each age group earning a spot for the UCI Gran Fondo World Championships.

For those who prefer a more leisurely ride, the event offers the Chief Ladiga Cruise, a family-friendly ride on the Chief Ladiga Trail, a paved rail trail. The Chief Ladiga Cruise offers three distance options: 50 miles, 25 miles, and 12 miles, starting and finishing at the Pete Mathews Coliseum on Jacksonville State University’s campus.