New Yorkers are tough but the Gran Fondo New York championship, which is in close proximity to the city, may challenge that statement. The 100-mile course is physically very demanding. Bikers will race against each other and the clock from NYC to Bear Mountain and back. There is a second, 50-mile non-competitive ride on the same day. Consider the absolutely gorgeous scenery just a bonus.
Rebecca’s Private Idaho involves pedaling among some of the most stunning valleys and mountains there. The grinder of a ride is challenging because of the hills and altitude. It starts out at 6,000 feet in Ketchum. By the end of the day, you will have crested 8,000 feet twice with a lot of smaller climbs in between. Overall, you will have tracked in about 6,500 feet of climbing in nearly 100 miles. Seeing the historical Wagon Days Parade, the largest parade in the country without motorized vehicles, is a nice way of relaxing afterwards.
The TransRockies Run is a 6-day point-to-point trail running race. It is one of the most scenic events in the world. You can do it as a relay or individual. Athletes will complete 120 miles from Buena Vista to Beaver Creek, Colorado. The vertical gain is about 20,000 feet. At some point, you will find yourself on a steep and narrow dirt trail on a windswept ridge in the Rocky Mountains, but the view alone will be worth it.
The Flowers Sea Swim is a challenging and a beautiful open water swim event (1 mile, 5K, 10K). Visit and take a selfie with a stingray at Stingray City, a series of shallow sandbars found in the North Sound of Grand Cayman, Cayman Islands. Snorkeling and diving at outer islands and eating local seafood are other favorite activities. You’ll also get a chance to swim with Olympians (current and former).
This is the most challenging way to see this gorgeous area. Cycle Adirondacks is the first fully supported annual road bike tour of the Adirondack Park. The average mileage is 60-65 miles per day, but there are options for 198 to 426 miles. Some perks include free beer from local brewery each night, farm to table food, free massage, nightly entertainment, awesome excursions and fun for non-riding family members.
The Marathon du Medoc has been elected the most convivial race in France four times, three of them were in a row. The event is all about the fun. You get wine at the aid stations in Bordeaux. Do you really need anything else? However, it’s also a real marathon. You’ll run 42.195 kilometers, 26.21 miles. There is a costume theme every year.
You get to play a “resident of the facility” and use the exact same escape route from the famous prison. The challenge in the Escape from Alcatraz Triathlon comes from the cold water, sharks and tough current. The terrain on the ground is a hilly course. The event includes a 1.5-mile swim from Alcatraz Island. The race continues with an 18-mile bike ride out the Great Highway, through the Golden Gate Park, and concludes with an 8-mile run through the Golden Gate National Recreation Area.
During the Hincapie Gran Fondo you get to ride with some of the most famous American cyclists. The race also offers gorgeous and challenging ride options and a celebrity chef dinner. There are three possible rides: 15, 50 and 80 miles. The last one involves climbing the infamous Skyuka Mountain KOM, switchbacks on Green River Cove and a challenging descent down Howard’s Gap.
If you plan a vacation to San Diego around Labor Day in September, why not look into participating in America’s Premier Rough Water Swim? You can join the 250 yards race or the one or three miles ones. You will enjoy the majestic view of the La Jolla Cove, around which the marine life is plentiful. The water is pristine and the temperature is around 60 degrees. The race began in 1916 with seven men. It has grown so much; organizers put a cap of 2,000 swimmers.
L’Etape Du Tour gives you the opportunity to ride an actual stage of the Tour de France, under the same conditions as the professionals. Every year, it’s another mountain stage of the Tour but passing through the same stage towns, the same routes, the same mythical climbs. The race is fully supported and incredibly challenging. Riding through some of the most beautiful places in France makes the event a tourist adventure.
Hood To Coast is a massive 198 miles long event. Known as "The Mother of All Relays", HTC is the largest relay in the world. You will be competing with 12,600 runners. HTC is also the longest running relay event in Oregon and hosts the largest beach party on the west coast, according to its website. The race consists of 36 legs. Each runner is required to complete three of them.
The Comrades Marathon is one of the most popular and difficult marathons in the world. It alternates uphill and downhill every year. This year is a “DOWN RUN.” The race distance is approximately 90 kilometers (56 miles). It’s already too late to sign up but keep this event in mind for 2017. The destination in South Africa is amazing. You can go on a safari, surf in Durban, go shark diving, or drive the Garden Route.
The 26.2-mile Inca Trail Marathon on measured course is described as “The Most Difficult Marathon in the World,” but it’s also one of the most inspiring vacations you can imagine. The race includes over 10,000 feet of elevation gain, two high passes (13,000 and 13,800 feet), and thousands of Inca steps. The event is fully supported. This year’s race is already sold out so book a trip for next year.
The Nautica Malibu Triathlon is one of the most beautiful races in the U.S. Aside from breathtaking views and swim in the Pacific Ocean; you get a chance to race with celebrities and Olympians. The course includes a half-mile ocean swim, an 18-mile out-and-back bike course, and a 4-mile out-and-back run course.
The Mount Washington Auto Road Bicycle Hillclimb is known as one of the toughest hill climbs in the world at 7.6 miles in length. It has an average grade of 12 percent with extended sections of 18 percent, and the last 50 yards is an amazing 22 percent. One of the most challenging factors is the unpredictable weather. You can ride for free: If you register at $350 and collect pledges for $350.00, TMCC will send you $350.
The Leadville Trail MTB 100 will take you 100 miles across the high-altitude, extreme terrain of the Colorado Rockies. The race takes a lot of skills – it starts at 10,000 feet and you ride upwards to more than 12,000 feet. The stunning views make the ride much better. The course will consist of roughly 50 percent dirt road and 50 percent fast, single track with a great flow.
The Challenge Roth is the Tour de France of triathlon. It’s exciting, thrilling, challenging, and very beautiful. Jan Frodeno, who won gold at the Olympic Games in Beijing in 2008, and is the current Ironman Hawaii champion, says Roth was is highlight of his career. "The event in Roth is a European triathlon legend,” he says. The race is a five-time winner of the “Race of the Year” award.
The Yellowstone Half Marathon is in one of the most beautiful national parks in the world. It’s home to hot springs, waterfalls and its own grand canyon. The 12-mile race, which gets quite technical at time, takes place on a dirt road and trail in Gallatin National Forest. Mile 6 is the most difficult section because that’s when you start running uphill. You will gain about 200 feet in elevation.