Jessie Herling: An Admirable Outdoorswoman

Once in a while I meet someone who makes a certain kind of impression. Maybe it’s their style of clothing or something witty I overheard them say. The co-manager of U.S. Rafting is such a person. She checked us into The Outpost then went about her work, but when she had a little free time, she came back to visit. Three minutes into the conversation, I knew I wanted to tell more than a story about rafting. I wanted you to meet an impressive outdoorswoman name Jessie Herling.

The first question I asked Jessie was what made her want to be a whitewater rafting guide. “Blame my mom for that,” she replied. Jessie was in the second semester of her junior year of college, studying to be an engineer, when she called her mom. Through tears, she told her mom how unhappy she was in college, in engineering, and in being a cubicle worker while she gained practical experience.

“I’m not a nine to fiver and I can’t sit still.” Her mom suggested Jessie go on a soul searching trip. She sent her whitewater rafting on the Yompa River in Utah for a week. Jessie arrived to find herself the only unpaired person in the group. Everyone else had a partner, spouse or friends. Her guide was a young woman Jessie’s age. They got to know each other in and out of the raft. Jessie loved the whitewater, rafting and the people it attracts. She went home knowing what she really wanted to do and the lifestyle she wanted to lead.

Two semesters away from her engineering degree, Jessie left college.

Jessie’s first day in training to be a whitewater rafting guide was rough. She and other trainees were thrown into the icy cold river at Goodbye Hole. Jessie rode it out with nothing but her PFD and paddle. “I was like a wet noodle when I got back in the raft but I still had my paddle. You can’t guide if you don’t have a paddle. Tom was smitten. We’ve been together ever since.”  Tom told me the same story, right down to “and I was smitten.”

Some of the trainees left that day. Jessie stayed. “It’s still cold when we start training. It’s a good way to find out who can do it early and let the rest go home,” Tom told me. He’s a strong family man. You can see how much he loves his wife and children when you mention their names. Jessie and Tom now co-manage U.S. Rafting.

Tom brought Collin, his now eight year old son, into the marriage. Together, Jessie and Tom have six year old Aiden and four month old Sianna. When I met Jessie, Collin was visiting for the summer. He lives in Alaska with his mom.  Jessie is working full time, lives on site, is seldom away from work even on her days off, and she’s doing it with kids in tow.

Jessie and Tom Herling with Aiden and Sianna. Collin was more interested in eating than having his picture taken. He is a growing boy, after all.

The Herlings live at the base. It’s convenient to be at home when you’re also at work. “I can do everything with the kids with me. I don’t have to send them to day care. Tom and I live, work and play together here. But it also means I’m here at 3 am when someone calls from The Outpost to say the toilet is plugged up.”

She’s not guiding this year because Sianna was born just before the beginning of the whitewater season. She stays at base to keep things running, cleans The Outpost and keeps everything running smoothly. “The first time I got in a raft after Sianna was born I realized my muscles were not going to be up to it at the beginning of the season.”

Jessie is one of only two female whitewater rafting guides at U.S. Rafting. Meredith Wheeler pitches in to tackle problems big and small and helps Jessie get things done when she’s not guiding a raft full of excited people down the Kennebec River. They’re a good team and each speaks highly of the other. Meredith is a junior high science teacher during the school year.

What’s it like to be only one of two women at U.S. Rafting? “As weird as it sounds, I love it,” Jessie said. “Being the first women brought a lot of respect. They tested me the first year. I do all this with kids and that earned more respect.”

Jessie keeps an eye out for people. She smiled when I asked her about guides. Cory Thibodeau is a young guide from Weare, NH. This is his second year as a guide. He said being a guide “is fun. I enjoy taking the first timers and kids.” Jessie said being a mom, she knows when something might be wrong and she’s there if something needs to be fixed.

Cory Thibodea is a whitewater rafting guide. He enjoys guiding first timers and kids the most.

I asked Jessie how she manages to get everything done with three kids, a husband and a full time job. “I’m good at delegating so I don’t get burned out. I’m a mother. I can tell people when I need them to do something.” And she truly loves being a guide. “I meet a lot of fun people. I go the grocery store and recognize people. I had my mom and brother and two nurses from Portland with me on my last trip before I found out I was pregnant with Aiden. Aiden was a NICU baby at the hospital in Portland when he was born. I looked at the nurse a couple of times and then she said, ‘You took me rafting.’ I took care of her and she took care of me.”

Collin and Aiden love rafting as much as their parents do. Collin jumped into our raft when we passed the last rapid on my first rafting trip. He’s too young to be in the raft on rapids during a commercial ride. I imagine adorable Miss Sianna will rock the river just like her mom.

Jessie is an adrenaline junkie. She’s had her private pilot’s license since she was 21. “Flying in the winter is smoother. There aren’t any hot air pockets causing turbulence.”

As if she isn’t busy enough, Jessie doesn’t take the winter off. She works at Sunday River managing ticket and group sales and she bartends at Suds Pub. She does scheduling for groups, lodging and dining.

Jessie Sterling is one of the most impressive outdoorswomen I’ve met.

Robin Follette

About Robin Follette

Maine Press Association award winner, 2013. Robin's Outdoors, Bangor Daily News, third place in Sports blogs. I grew up with a fishing pole in my hand and have always loved the outdoors. From gardening to hunting and fishing, kayaking, camping, hiking and foraging, most of my time is spent outdoors. I teach outdoor skills as a volunteer instructor for Hooked On Fishing - Not On Drugs and Becoming an Outdoors-Woman. Pro-staff at The Limb Grip. My personal blog is here. I'm currently working on my first book, a collection of short stories based on my outdoors experiences.