The 25 Most Adventurous Women of the Past 25 Years

Keala Kennelly

On July 2015 Hawaiian surfer Keala Kennelly towed into and rode one of the biggest waves ever ridden by a woman at the legendary surf break, Teahupo’o.

“I rode deep inside a huge cavern of water until the foam ball vaporized me, and then I took a horrendous beating,” says Kennelly. “When I look at the pictures of that wave and how thick and scary it was, I can’t believe I walked away from that experience.”

It was the stuff of legend and won her the 2016 Barrel of the Year Award at the XXL Big Wave Awards — an award that had only been won by men previously. This proud ride came a decade after Kennelly became the first woman ever to tow into Teahupo’o.

Kennelly became a pro surfer at age 17 and spent 11 years competing at the highest level on the ASP World Championship Tour.

“Competitive surfing is fun when you are winning, but it sucks when you loose. It can be draining to be constantly judged and compared to others,” says Kennelly of why she shifter her focus to riding big waves. “The thing I love about big-wave surfing is that it’s more about you versus nature. There is a lot more adrenaline involved because you are putting your life on the line. It’s quite a rush.”

Kennelly’s surf career has been nothing short of prolific. Her mastery of competition surfing as well as the monster waves she’s ridden puts her in a class all her own. She’s such a badass that she actually played herself in the 2002 surf film Blue Crush.

When asked what the greatest challenge women surfers face, she said: “Being respected for their surfing ability not their sex appeal and not being compared to the men who are biologically built differently.”

Noteworthy Feats

• 2015: Surfs the biggest wave ever at Teahupo’o.
• 2011: Crashes into reef at Teahupo’o and practically rips face off.
• 2005: First woman to tow into Teahupo’o.
• 2003: Runner up to World Title in ASP World Championship Tour.

Rebecca Rusch

“I love to use my bike as the ultimate tool for exploration and to see the world,” says mountain biker Rebecca Rusch, known as the “queen of pain” for her ability to excel in endurance sufferfests, such as Colorado’s epic Leadville Trail 100, which she has won four times. It was that need to explore that led her to her most challenging ride — 1,200 miles through Vietnam, Laos, and Cambodia in 2015 to look for the remains of her father, a fighter pilot who was shot down in the Vietnam War.

“Riding the Ho Chi Minh Trail was the culmination of everything I’ve learned and trained for in my entire career,” says Rusch, who has also biked up and down Tanzania’s Mount Kilimanjaro. “It challenged me physically, but emotionally it was such a big personal journey that I came home a different person.” Her story is told in the new film Blood Road, which comes out this spring. 

“I also came home with a new mission to do my part to help with the cleanup of the unexploded land mines that still exist there,” says Rusch, who is also a firefighter in Ketchum, Idaho, and has been running women’s mountain biking clinics for five years.

“Finding a purpose to use my bike as a vehicle for change was a powerful experience and gave me focus for perhaps what I’ve been chasing all these years,” says Rusch. “I do believe that the world is a better place if everyone goes outside and gets sweaty and dirty.”

Noteworthy Feats

• 2001: First female self-supported expedition river boarding down the Grand Canyon.
• 2007, 2008, 2009: 24-hour solo MTB World Champion.
• 2009, 2010, 2011, 2012: Leadville Trail 100 women’s champion.
• 2015: Rode length of the Ho Chi Minh Trail.
• 2016: Rode up and down Mount Kilimanjaro to support World Bicycle Relief.