Best Cycling Events in the US

Finding the best cycling events in the US has gotten complicated with all the new races, gran fondos, and charity rides flying around. As someone who has ridden everything from casual century rides to brutal gravel races across multiple states, I learned everything there is to know about what makes a cycling event worth your time and entry fee. Today, I will share it all with you.

The American cycling scene is absolutely stacked right now. Whether you want to suffer through a mountain pass in Colorado, cruise through Iowa cornfields with ten thousand of your closest friends, or grind gravel until your arms go numb — there’s an event for that. Here are the ones I think every cyclist should have on their radar.

Tour of California

This is the big one for US road cycling. The Tour of California pulls in world-class pros and covers terrain that’ll make your legs scream just looking at the elevation profiles. Mountain passes, Pacific coast roads, vineyards — it’s basically a cycling postcard crossed with a suffer-fest. I watched a stage in person once near Big Sur and honestly, seeing the peloton fly by at that speed in real life is something else entirely.

RAGBRAI (Register’s Annual Great Bicycle Ride Across Iowa)

That’s what makes RAGBRAI endearing to us cycling enthusiasts — it’s not about racing at all. It’s the oldest, biggest, and longest recreational bike touring event on the planet, and the vibe is unmatched. Thousands of riders rolling through small Iowa towns where the entire population comes out to feed you pie and cheer you on. The camaraderie is genuine. I’ve made lifelong friends on RAGBRAI. You camp out, eat incredible local food, and pedal through countryside that’s way prettier than anyone gives Iowa credit for.

Dirty Kanza

Now called Unbound Gravel, but plenty of us still call it Dirty Kanza. This 200-mile gravel monster in Emporia, Kansas, is no joke. The Flint Hills terrain looks gentle until you’re 120 miles in, battling headwinds and wondering why you ever thought this was a good idea. The conditions can swing from perfect to apocalyptic — I’ve heard of years with waist-deep water crossings. If you want to test what you’re actually made of, this is the race to do it.

Leadville Trail 100 MTB

Probably should have led with this section, honestly. Leadville is the most iconic mountain bike race in America and maybe the world. One hundred miles starting at 10,000+ feet of elevation in the Colorado Rockies. The air is thin, the climbs are relentless, and the course will humble even experienced riders. Getting under the coveted sub-9-hour belt buckle is a goal that drives people to train for years. Lance Armstrong raced it. So did regular mortals who just wanted to see if they could.

Sea Otter Classic

Sea Otter in Monterey is part race, part festival, part massive bike expo. You’ve got cross-country, downhill, road races, and short track events all happening alongside vendors showing off the latest gear. The scenery along the Laguna Seca area is beautiful, and the energy of having every type of cyclist in one place is pretty special. Great event for families too.

The Triple Bypass

Three mountain passes. 120 miles. Colorado. Yeah, it’s as hard as it sounds. The elevation changes are absolutely punishing, but riders who finish it talk about the experience like it changed them. The mountain scenery is world-class, and there’s a real sense of accomplishment at the end that you just don’t get from flatter rides. This one’s for the seasoned cyclists who want to push their limits.

Chequamegon Fat Tire Festival

Wisconsin doesn’t get enough credit for its mountain biking, and Chequamegon proves why it should. Off-road racing through gorgeous northern Wisconsin forests with fall colors as a backdrop. The community atmosphere is incredible — families camp out, there’s food and music, and the trails are genuinely fun to ride. It’s competitive if you want it to be, but most folks are there for the experience.

Tour de Tucson

Arizona in November is about as perfect as cycling weather gets. The Tour de Tucson offers multiple distance options through stunning desert scenery that looks like another planet if you’re used to riding in the Midwest or Northeast. It’s well-organized with great support, and the route offers enough variety to keep things interesting even at the shorter distances.

Great Allegheny Passage (GAP) Trail

Not technically an event, but I’m including it because riding the GAP is something every cyclist should do at least once. 150 miles from Pittsburgh to Cumberland, Maryland, on a crushed limestone rail trail. It’s gentle, scenic, and passes through gorgeous Appalachian scenery and historic sites. Perfect for a multi-day bikepacking trip. My wife and I did it over three days and it was one of our best cycling memories.

The Five Boro Bike Tour

40,000 cyclists riding through all five boroughs of New York City on closed roads. Where else can you pedal across the Verrazano Bridge with no cars? It’s completely non-competitive — the point is soaking in the city from a perspective you literally cannot get any other way. I’d recommend it even to non-cyclists. It’s just a joyful day.

Gran Fondo Hincapie

Named after George Hincapie, one of the greatest American domestiques in Tour de France history. Set in Greenville, South Carolina, it offers a professional-level experience for amateur riders. The roads are beautiful, the climbs are real, and the whole thing is organized like a pro race. Multiple route options mean you can pick your poison. The longer routes have some seriously demanding climbs through the Blue Ridge foothills.

The Assault on Mount Mitchell

102 miles to the highest peak east of the Mississippi. That’s the sales pitch, and it doesn’t need embellishment. Starting in Spartanburg, South Carolina, and climbing relentlessly into North Carolina, this ride is a true test of legs and lungs. The final push to the summit of Mount Mitchell at 6,684 feet is brutal, but standing at the top knowing you rode there from near sea level? Incredible feeling.

Iron Horse Bicycle Classic

Cyclists racing a narrow-gauge steam train from Durango to Silverton, Colorado. The concept alone makes this event legendary. The 50-mile route involves serious mountain climbing at altitude, and yes — some riders actually beat the train. The scenery through the San Juan Mountains is jaw-dropping, and Durango itself is one of the best cycling towns in America.

Hotter’N Hell Hundred

100 miles in Wichita Falls, Texas. In August. The heat is exactly what you’re imagining, maybe worse. This is one of the largest cycling events in the country, and it’s essentially a battle against the thermometer. Proper hydration strategy is everything here. Despite the brutal conditions (or maybe because of them), thousands of riders show up every year. Finishing Hotter’N Hell is a badge of honor.

MS 150 Bike Rides

These charity rides happen all over the country to support the National MS Society. Typically 150 miles over two days, they’re accessible to riders of varying abilities and the cause gives the whole thing a deeper meaning. The community element is huge — teams train together for months and the ride itself feels like a moving celebration. I’ve done two of them and the energy is always positive.

Mount Washington Auto Road Bicycle Hillclimb

7.6 miles. 4,727 feet of climbing. Average grade of nearly 12%. And the weather at the summit can be genuinely dangerous — Mount Washington holds the record for the highest wind speed ever recorded on Earth’s surface. Only a limited number of riders get in each year, and it’s considered one of the hardest hillclimbs you can do. Short, vicious, and unforgettable.

The Death Ride (Tour of the California Alps)

Five mountain passes over 129 miles with 15,000 feet of total climbing. It’s called the Death Ride for a reason. Starting in Markleeville, California, this event has a cult following among masochistic climbing enthusiasts. The alpine scenery is stunning, but you won’t notice much of it when your heart rate is pinned at threshold for hours. Finishing all five passes is the goal, and not everyone does.

Idaho Ride to Defeat ALS

Part of a national series raising funds for ALS research. The Idaho edition features scenic routes that showcase the state’s underrated beauty. It’s more about the cause than competition, which creates a supportive and fulfilling atmosphere. A great ride for anyone who wants their cycling to mean something beyond personal fitness.

Hell of the North Texas

A gravel race in Paris, Texas, that lives up to its name. 75 miles of challenging terrain, unpredictable weather, and the kind of suffering that gravel racing people apparently enjoy. It’s gained a loyal following among the Texas gravel scene and the racing is always hard-fought. If you like your rides with a side of pain, this one delivers.

Tour de Georgia

Currently not active, which is a real shame. In its heyday, it was a premier US stage race featuring top professional talent on challenging Georgia courses. Beautiful scenery, strong competition, and great community support. There have been ongoing discussions about reviving it, and honestly, the US cycling calendar could use it. Fingers crossed.