Gran Fondo means “great distance” or “great endurance” to cyclists, but this only tells about part of the story. The best gran fondos recall 100 years of Italian cycling tradition with routes that trace the most famous mountain passes and historic races in cycling history, and they’re also becoming more popular in the U.S. Unlike your typical chilled-out century ride, fondos reward the fastest times in age groups with prizes, so expect this to be more like a competitive group ride than a casual cruise with coffee stops; the course is usually offered in multiple distances ranging from 30 miles to nearly 200 miles, and with degrees of difficulty varying from flat routes to sections with extremely steep climbs. And then there’s the hallmark of each event: the post-ride celebration, with plentiful food and wine. These five from around the world are the most worthy of your bucket list.

MORE CYCLING: Best Road Bikes | Photo Essay: Red Hook Crit | Photo Essay: Act Two for American Cycling

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Campagnolo Gran Fondo New York

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Date: May 18th, 2014
Location: New York, NY

Vital Data

Distance: 101.0 mile
Elevation: 8,163 feet
Moving Time: 5:07:17
Calories: 3,736

6,000 cyclist stage themselves on the George Washington bridge as they embark on a 100-mile ride through some of the finest roads New York has to offer. The highlight of the day is the category-2 climb up Bear Mountain, where riders are met with a carnival-like atmosphere and spectacular views of the Hudson Valley — with the cityscape just peeking through the rolling hills. This fondo offers a 50-mile and 100-mile option; those who sign up for the latter get to enjoy 8,000 feet of climbing.

Gran Fondo Milan San Remo

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Date: June 8th, 2014
Location: Milan, Italy

Vital Data

Distance: 189 miles
Elevation: 13,162.7 feet
Moving Time: 7:36:59

The gran fondo Milan – San Remo is the event for the guy who wants to take a spin on one of the oldest and longest single day events in pro cycling. The route has been known to favor sprinters, but only if they can hang on over the top of the Passo Del Turchino climb, which last for nearly 20 kilometers. The race is a difficult one, with a point-to-point 185-mile route with 7,000 feet of climbing.

Marmotte Gran Fondo

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Date: July, 5 2014
Location: Le Bourg-d’Oisans, France

Vital Data

Distance: 109 miles
Elevation: 16,404 feet
Moving Time: 7:52:15
Calories: 7,201

Marmotte is a spectacular single day of cycling for those who have watched the epic battles unfold in the French Alps every July during the Tour de France. This single day event takes you over the Glandon, Telegraphe, and Galibier passes and finishes on top of Alpe d’Huez, which has been featured as a finish line 28 times in the Tour. If you are feeling spry at the end of the day you can try to break the late Marco Pantani’s Alpe d’Huez record of 00:37:35. The Marmotte gran fondo covers 110 miles with nearly 15,000 feet of climbing.

Levi Leipheimer’s King Ridge Gran Fondo

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Date: October 4th, 2014
Location: Santa Rosa, CA

Vital Data

Distance: 99.7 miles
Elevation: 7,893 feet
Moving Time: 5:32:22
Calories: 4,335

Levi Leipheimer’s King Ridge Gran Fondo is a charity ride that promises a route for any type of rider with any level of fitness. Each of the three routes (32, 65 and 103 miles) starts and finishes in Santa Rosa, CA — but if you choose the 103-mile route with 8,000 feet of climbing, you’ll be in for a long day as you make your way over mountain passes, ride along ridges and face the headwind from the Pacific Ocean from around mile 60 through 80. The 4,000 calories you burn off can be replenished with paella and beer at the post-ride party.

Hincapie Gran Fondo

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Date: October 25, 2014
Location: Greenville, SC

Vital Data

Distance: 79.7 miles
Elevation: 7,529 feet
Moving Time: 4:44:47
Calories: 3,808

Southern hospitality, fall air and the foothills of South Carolina — along with the cadre of pro racers George Hincapie brings into town — make this fondo a perfect way to close out the riding season. The course is 80 miles with 8,000 feet of climbing and ends with a festival at George’s Hotel Domestique.

And Don’t Miss

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