Last updated June 3, 2025
Strambecco rates the Best Road Cycling Races Southeast 2025 based on reputation, route quality, location, rider feedback, and the event’s or race’s overall uniqueness. Spanning North Carolina, South Carolina, Georgia, Florida, Alabama, Tennessee, Kentucky, and Mississippi — Southeast terrain features of Strambecco’s best list varies but include many events navigating parts of the Appalachian Mountains along with rolling hills, rich river valleys, and high flat plateaus. States in the lower part of the region offer significantly flatter terrain amidst beaches, swamps, and wetlands.
The most notable events on Strambecco’s list of best road cycling races Southeast 2025 are part of the Gran Fondo National Series, the largest and most competitive series of Gran Fondo cycling events in the United States. The series was the first to implement timed-segment racing into US gran fondo events, and since 2012, has crowned Gran Fondo National Champions in a variety of age/gender categories. In 2020, the series partnered with USA Cycling to bring a one-day Gran Fondo National Championship into the portfolio of official USA Cycling National Championship events. GFNS Southeast events include Tour of Georgia Gran Fondo, Gran Fondo Boone, Gran Fondo Asheville, and Gran Fondo Florida. Each event is a qualifying event for the National Championship event at Gran Fondo, Maryland, in September.
The Cheaha Challenge, a Gran Fondo National Series partner event, qualifies for the UCI Gran Fondo World Series, a series of long-distance cycling races held worldwide. These races are open to amateur cyclists who are looking to challenge themselves and compete against other riders from around the globe. The Series is organized by the Union Cycliste Internationale (UCI), the governing body for international cycling. The series comprises approximately 25 events, each featuring a challenging route through scenic landscapes. Strambecco rates many of the events, which you can see below or the full calendar of events here. One of the unique features of the Series is that it allows amateur cyclists to qualify for the UCI Gran Fondo World Championships held in late August this year in Denmark.
Strambecco does not list every event. We strive to identify and review events that are special and noteworthy. If you have suggestions on other events we should consider or review, please get in touch with us here or send us a note at editors@strambecco.com. Strambecco also rates the best MTB and best Gravel Events in the Southeast. [/vc_column_text][/vc_column][/vc_row]
This second leg of the Gran Fondo National Series delivers one of the most challenging courses in the series, winding through Appalachian terrain around Helen, Georgia. The routes crisscross the Appalachian Trail…
Founded by 16-time Tour de France finisher George Hincapie, this Tennessee gran fondo delivers three distinct challenges from the heart of Chattanooga. What sets it apart is the dramatic terrain variety and…
Now in its 31st year, the Cheaha Challenge Gran Fondo stands as Alabama’s premier cycling event, starting from Jacksonville State University. What sets this event apart is its brutal climbing profile and…
The Knoxville Gran Fondo takes riders through the rolling hills and scenic backroads of South Knoxville, featuring a mix of challenging climbs and rewarding descents that showcase the natural beauty of East…
This second leg of the prestigious Gran Fondo National Series showcases Asheville’s unique blend of pastoral countryside and mountain ridge vistas through a course that starts with punchy climbs and finishes with…
For more than 20 years, the Hot Hundred has held its reputation as one of the premier century rides in the Southeast. Established in 2003 and organized by Druid City Bicycle Club,…
The Boone Gran Fondo delivers one of the more challenging courses in the Gran Fondo National Series, set against the backdrop of North Carolina’s High Country. Held in early August when temperatures…
This 30+ year North Carolina institution delivers exactly what its name promises: a brutal test through the Blue Ridge Mountains that combines punishing climbs with stunning parkway scenery. The event offers four…
The ELK River Valley 100 rolls through middle Tennessee’s scenic countryside at the end of August, offering four timed route options: 31, 62, 80, and 100 miles. Based in Tullahoma, the event…
Set amidst the rolling hills of Dahlonega, Georgia, the Six Gap Century stands as one of the most challenging cycling events in the Southeast. This 104-mile odyssey delivers over 11,200 feet of…
This Virginia mountain challenge earned recognition as one of “America’s Top-10 Gran Fondos” by Men’s Journal, and the terrain explains why. The flagship 110-mile route tackles significant mountain climbs through the Shenandoah…
This cycling event transforms the Blue Ridge Mountains of South Carolina into a training ground reminiscent of George Hincapie’s Tour de France preparations. Based at Hotel Domestique, 20 miles north of Greenville,…
GFNY Florida Sebring takes place in the heart of “old Florida,” showcasing the state’s most picturesque landscapes away from coastal crowds. The event starts in historic downtown Sebring, a century-old city built…
