Cyclo-Cross is an exciting form of bicycle racing held during fall/winter months. Sometimes know as the "steeplechase" of bicycle racing, cyclo-cross combines elements of road racing, criterium racing and mountain bike racing into a sport raced on avariety of surfaces. Cyclo-Cross is a timed event held over a course 2.5km-3.5km in length with multiple laps raced by the riders. Courses take racers over a combination of terrain such as asphalt road, grass, dirt paths, mud, gravel and sand. Cyclo-cross rcaing is about transitions from one type of surface to another, from one section to another, from one speed to another. Races are held in all sorts of weather conditions and are rarely cancelled. Cyclo-cross bikes look like road bikes but have cantilever style brakes and knobby tires. During some parts of the course there are areas that may require a rider to dismount and carry or run with the bicycle. Modern cyclo-cross courses can have one set of artificial barriers (usually boards 40cm high set 4 meter apart). Steep hills, mud and sand also force ridres to dismount.

The North Carolina Cyclo-Cross Series started in 1997. The series came about as a result of the Diamond Brand Series, a local 4 race series held in Hendersonville, NC during 1995-1997. The series at the time featured two cyclo-cross races and two mountain bike races and was sponsored by the Diamond Brand Camping Center.

In 1997-1998 the first NC series featured 14 races spaning from the beginning of November 1997 through the end of February 1998. Races were held in Cary, Greensboro, Southern Pines, Boone, Asheville, Bryson City, Hendersonville, and Andrews. The Liberty Bicycles/NC Cyclo-Cross State Championships were held on February 22, 1998. These were probably the first USCF State Championships held in NC. The winners were Men's A - Chris Brown (Asheville/Cane Creek), Men's B - Breck Cartwright (Asheville/ABRC), Master's 35+ - Joe Cline (Chisholm/Chapel Hill), Women - Willow Koerber (Hosre Shoe/Cane Creek), Men's C - Chris Ernst (Cherokee/GT Trail Head)

In 1998-1999 and for the next three seasons SUBARU was the title sponsor of the series. During the four years SUBARU was involved the series grew from 13 races in 1998-99 to 18 races in 2001-2002. Races continued to be held across the state in venues from the coast to the mountains.

In 2002-2003 Wood Automotive of Transylvania County stepped in as the series sponsor. After the mammoth 18 race season in 2001-2002 a decision was made to create two series. The North Carolina Cyclo-Cross Series was held during October, November and December of 2001 and ended the weekend before Cyclo-Cross Nationals. Then during January of 2002 the Winter Cup was held. This second series featured 5 races over three weekends. During the first year of the Winter Cup four members of the US National Cyclo-Cross team came to train. Adam Craig, Josh Anthony, Jesse Anthony and Ryan Trebon all participated in the Winter Cup before heading to Monopoli, Italy.

In 2003-2004 and 2004-2005 the North Carolina Cyclo-Cross Series and Winter Cup continued without a title sponsor. Financial Assistance from the Asheville Bicycle Racing Club, Sandhills Cycling Club and attorney Tom Ramer ensured that the same high standards set in previous years were continued. During the 2004-2005 season a record 1290 participants raced in the cyclo-cross events.