REI Presents: Pedal Through

The following article was originally published by Travel Oregon. Available to read here.

Analise Cleopatra had never ridden a mountain bike before. The 29-year-old Portland filmmaker had never gone camping, either, and she suffers from long-term anxiety. Yet in September 2019, she embarked on a major adventure to push herself out of her comfort zone: She went bikepacking. 

That’s a combination of biking and backpacking, meaning riders carry all their camping gear on their bikes as they ride. In this case, it was 15 to 30 miles for six days in a row, over gravel and dirt trails through Oregon’s Willamette Valley and Central Oregon. She was up for the challenge. “I want people who have never biked or never camped before to see how healing it could be,” she says.

A Voice for Young Artists

Cleopatra, a Miami native, moved to Portland in 2013 to become a sneaker designer after a short trip to Portland for Design Week. During her classes at Pensole Design Academy, her love for sneaker design turned into a desire to create her own visuals. “I spent a lot of time interrogating the [school’s] production crew about how things worked and why they were doing this and that, and felt like there was an opportunity there to tell my own stories too,” she says.

Cleopatra realized she wanted to be a voice for young Black artists, but she soon found she could serve that mission better as a filmmaker. For her, there were a lot of untold Black stories, and she wanted to fill in those gaps and contribute to sharing them with the world.

That’s when 37-year-old Portland-based filmmaker and photographer Aly Nicklas came into the picture. They crossed paths when Cleopatra served as voice talent for a project Nicklas was working on. As their relationship grew, they decided to apply for an Oregon Made Creative Foundation grant in partnership with Travel Oregon.

Nicklas—an avid cyclist, runner, snow-sport adventurer and all-around outdoorsperson—had come up with the idea to feature Cleopatra’s journey as a beginner on a weeklong, 323-mile bikepacking trail through Oregon’s backcountry. They had no expectation that they’d win the grant.

“I thought it was a great opportunity. I don’t know anything about this, but I’d try and do my best,” Cleopatra recalls. While Nicklas had five years of mountain biking under her belt, she helped show Cleopatra the ropes. But her cycling skills were the least of her problems.

Channeling the Fear

Cleopatra has been dealing with anxiety since high school and started seeing a counselor in college, but she didn’t find the relief she needed until years later. After seeing a therapist in Portland, she started taking medication for ADHD, which helped her anxiety. She says medication is not something therapists recommend for everyone, but it was helpful with regulating her moods.

At the thought of being around strangers, not having any privacy and riding 15 to 30 miles a day during a bikepacking trip, she naturally had a lot of worries. “I think I was very anxious, because for me, when I’m entering a new space, I generally like to hang back and observe how people move in that space, so I kind of know what to expect,” she says. “Since that wasn’t something I could do here, I just had to dive in and be open about it.”

Without time to adjust or medication to use at the time, Cleopatra had to filter between anxiety and reality on the trip—despite the company of her friend, fellow beginner Dejuanae Toliver, and professional mountain biker and social media influencer Brooklyn Bell. “I just had so many what-ifs, and I just wasn’t sure what was a reasonable fear or not, and it was just something you had to do, to learn and not to be scared,” Cleopatra says.

Finding Peace in Nature

As it turned out, bikepacking and being out in nature is what brought her peace and allowed her to move at a slower pace. She says the COVID quarantine has provided the perfect opportunity to reimagine recreation and create a path for people—specifically from diverse backgrounds—to try something new. 

In the end, the bikepacking group of women rode 132 miles in their soul-searching expedition. Cleopatra says she’s the strongest and healthiest she’s ever felt. “I’m so much less anxious because of the things that I now know that I can do with my body,” she says. “That’s something I would love every person to experience. It feels like flying.”

Her advice to outdoor adventurers just getting started? Be scared, and do it anyway.

If You Go: 

If you’re interested in tackling beginner-friendly and challenging terrain on a daylong adventure, here are some popular mountain biking hot spots along Cleopatra’s bikepacking route in Oregon. 


A bit east of Salem, Silver Falls State Park provides moderate uphill trail rides starting with the Catamount Trail Loop. This 12.3-mile singletrack loop climbs up 1,391 feet and has riders experiencing some rough, rocky sections as they capture beautiful views of the state park.

McKenzie River Trail 

The McKenzie River Trail is known as one of the best trails on the West Coast, the perfect ride to catch a glimpse of the crystal-clear blue pools in the Willamette National Forest. Starting at Clear Lake, ride downhill to the town of Rainbow, ending with a soak at Belknap Hot Springs. It’s part of the larger Three Sisters Three Rivers trail, of which the group rode about one-third. 


Not only is Oakridge famous for having the longest covered bridge in Oregon, but it’s also home to a popular Lower Alpine Trail. This easy, downhill-only trail is the original backcountry ride that put Oakridge on the map. Spend 9 miles in deep forests riding on narrow singletrack before riding 14 miles back to town for a craft beer on the patio at 3 Legged Crane Pub and Brewhouse.