Running the Trails While Running a Business

November 21, 2025/Bailey O'Brien

One late afternoon in October, just after a rainstorm ended and revealed a warm golden light beneath the clouds, Abby Clark and a friend went for a run on the Midslope Trail. Through the trees, they saw a glimpse of Casco Bay and a rainbow that seemed to end at Fort Gorges. By the time they finished their run, the sky had turned pink in a brilliant sunset. “One of my favorite runs by far,” said Abby in an Instagram video documenting the run.

It’s the latest video in her project to run — and create hand-drawn maps for — all the trails in Portland by the end of the year. By her count, that’s 33 trails, and she’s almost done.

Click to watch Abby’s video about her run on the Midslope Trail!

Abby, a 28-year-old graphic artist and photographer in Portland, is the owner of her own art and design company, Abby Clark Creative. Almost all the art she sells, which includes prints, cards, postcards, and stickers, incorporates hand-drawn maps, often overlaying her photography. “Maps are scientific,” she says, “but they’re beautiful works of art too.”

Her fascination with maps comes from her longstanding love for art and math. She originally thought she would have a career in architecture but instead changed course to follow her passion for creating art…and maps. A year after she moved to Portland in 2022, Abby took the plunge and opened her own business, pursuing her creative work full-time. Since then, she has sold her art, created custom designs, and worked with companies on branding, design, and photography. (In 2024, Abby photographed Portland Trails’ grand opening of the Improved Access Trail in Evergreen Woods!)

Abby in her studio surrounded by maps.

Two years in, Abby has experienced all sorts of ups and downs that come along with owning (and being the only employee of) her own business. “I get to make art that I want to be making, and I’ve found a niche of people who love what I make,” she says. “But my income fluctuates a lot. You always have to keep doing new things to keep getting attention, and money — especially on social media.”

The running videos she posts have brought her a bigger audience, she says. And more eyes on her social media pages means more people seeing (and potentially buying) her art.

Bass Harbor Light Film Map Print, available on her website, www.abbyclark.com.

But running on the trails is more than just a successful content creation strategy. “When I’m in a rut, I go for a run in the woods and feel ten times better,” she says. Preferring to run solo, she finds that she “zones out” when she’s on a trail and has the mental clarity to work through all the competing tasks and priorities she has to manage for her business.

Her current running and art project started in September during a time when she was in a running slump. Once she came up with the idea to run all the trails in Portland, she decided to hold herself accountable by sharing videos of her runs — and the accompanying art — on social media. Her friends check in with her about her progress, and strangers she meets at markets recognize her as “the one running all the trails.”

“Tandem on Peaks” Card, available on her website, www.abbyclark.com.

As of mid-November, Abby is on track to finish her goal and has five trails left. Her grand finale will be running the Forest City Trail, a 10-mile, cross-town trail that connects the Stroudwater River Trail all the way to the Presumpscot River Preserve. She plans to run that trail on December 2nd as part of Portland Trails’ Forest City Trail Challenge on Giving Tuesday! To pledge for each trail section she completes, or to make a one-time donation to her fundraiser, click here.

In addition to finishing her running project (and sharing the backlog of videos she’s made about each run), Abby is looking forward to the holiday market season — a busy but lucrative time for her business. But, she added with a laugh, she’s also looking forward to when it’s done.

You can follow her running project on her Instagram and TikTok, and you can check out all her artwork at www.abbyclark.com. Support Abby — and other local artists — at these five upcoming holiday markets: