There are few experiences more liberating than feeling the wind ripple through your hair and watching the world go by in a colorful blur as you coast down a hill on your bike. On my recent cycling tour through Italy, the Ciclismo Classico, I did just that- taking in the Italian landscape from behind my handlebars. Most of the time, cycling is a way for me to relax, to let go of whatever’s holding me back and learn to take life in stride. Cycling is more than just a hobby for me- it’s a way of life.

As much as I enjoy cycling to help me unwind, however, cycling can also be a challenge and I enjoy the challenge just as much as I cherish the rewards. There are few experiences more rewarding than the breathless exhaustion of making it up a challenging climb on your bike and taking in the seemingly endless expanse of world around you from your elevated vantage point.

While I have yet to partake in these expert-level mountain biking climbs, I’m gradually opening myself to new and more challenging cycling experiences. These are some of the challenging rides on my bucket list.

1. Death Ride, California

There’s no skirting around the truth here- the danger of this challenging bike ride is literally in the name! This upward trek through the California Alps, otherwise known as the “death ride,” lives up to its name because after covering all 129 miles of this race and climbing a total of 15,000 feet, you’re bound to feel like the death the next day. If you manage to complete the race, though, you’ll receive a complimentary Five-Pass Finisher’s Pin and you’ll be treated to a post ride dinner (whether you manage to finish or not). Sounds like a pretty good deal, considering the amazing views you’ll be treated to, and there’s nothing sweeter than the sense of accomplishment you get from pushing yourself to your limit, right?

2. Mauna Kea, Hawaii

If you think Hawaii is all about relaxing poolside with a fruity tropical drink, think again! This little slice of paradise is home to the most challenging bike climb in the world. According to, “Adjectives do not describe this climb.” Covering a total of 42 miles and an elevation gain of over 13,000 feet, this trek up a volcano is not for the faint of heart. You must be in prime physical shape to withstand the average grade and elevation, altitude, gravel, and changing weather conditions.

3. Mt. Washington, New Hampshire

This consistently steep hillside climb is more challenging than many mountain climbs because of the sheer difficulty of making it to the top through extended stretches with grades exceeding 12%. You don’t really understand what a grade that steep feels like until you experience it for yourself! describes it best: “This is the pittbull of U.S. climbs, sinking its teeth into you deep and early and not letting go until the top, all the while shaking the life out of your legs.” If this somehow still sounds appealing to you, just know that you’ll be treated to gorgeous views and a hearty turkey and potatoes meal afterwards.

4. Highlander Cycle Tour, New York

If you’re still with me, then you’ll definitely want to check out the annual Highlander Cycle Tour, whose proceeds go to charity, celebrating its 17th year this September. You’ll have to have grit to make it through all 100 miles and 10,000 feet of climbing, with some grades approaching 23 percent, but with the incomparable scenery of New York’s Finger Lakes Wine Country, you can bet it’ll be worth it.

5. Ride Westcliffe, Colorado

Just because this race starts at 7,900 miles above sea level, don’t think that makes it any easier than the others on this list! With three routes of varying difficulty to choose from, you’ll experience a “rocky mountain high” as you cover up to 10,000 feet of elevation gain with the 100-miles Century ride. As an added incentive, this fall event supports local charities such as the Custer County Kids’ Club and non-profit organizations supporting the region’s scenic and historic character.