Jessica Bobb

Let’s get to know Jessica Bobb of Grasonville, Maryland. She’s a mom of two girls, a high school math teacher, a coach for her kids’ sports teams and an ultrarunner who ran marathons long before 5ks. She’s got staying power and never met an ultra she didn’t like.  

When did you start running and why? 
I started running in college for stress relief and then for the physical and mental benefits I quickly learned it provided. I was playing division 2 softball (Seton Hill University in Greensburg, Penn.) and between butting heads with my coach, juggling a tough work load, and young adult struggles, I needed to run. It started with “hill” repeats, then runs through town, next thing you know I was running unofficial marathons and making all my friends wonder where I disappeared to for hours a day.  

Did you start with 5Ks? When did ultras enter the picture?
No, I never ran an official 5k until 2020.  My first official marathon was October 2010. 
I ran marathons until I had kids. Cut back but ran halfs while I was pregnant (each of my girls got a medal in my belly). Then in 2019, after having my two beautiful girls, I got back to it and after training for my first marathon back and exceeding my own expectations (both physically and mentally), I decided I had to keep at it. And then I saw a friend post on Facebook about Pemberton 24. His post got my attention and I convinced 3 friends to join me in the crazy. We were in it for fun, and a test. Oh, and none of us had ever ran trails.  

So my first ultra was Pemberton 24 in 2020 with a team that lost two of its members halfway through the night thanks to rolled ankles and broken spirits. I finished 17 laps that year, 53 miles, as the miscarriage I was going through came to a head. I had so many great conversations on the trails that year and fell in love with the ultrarunning community. The team member who made it to the end with me (I think she did 14 laps) and I decided next year we’d come back and do all 24. We found two strong team members and did just that. Not only did every one of our “Running Relentless” team members in 2021 do all 24, we won! One of my newly recruited team members, Megan, and I were born ultrarunners that year; together we strategized and gained a lot of place points for our team and had so much fun learning how to not fall on those trails. She also has continued on to do many hundred milers and podium in all kinds of races. We knew we could do 100 miles and I did my first a few months later in Michigan, June 2022.  

I never did a 50k, 100K, or 50 miler before jumping to the 100 miler. It was a 24-hour race and did the 100 miles in 21 hours. I quickly fell in love with the challenge. Now I search out the hardest ultras chasing my limits.  

What’s the farthest distance you’ve run?
103.4 miles at Eastern States 2025 in the PA wilds – Rocksylvania. Many say it’s one of the top 3 hardest 100s on the east coast. 2k up and down, 35 hours on the trails, no sleep.  I learned so much and I will be back and break 30 hours there.  

I think three times you’ve been on the podium for Pemberton 24 in the team category with Greenbackville Running Club. Tell us more about that. *DUC is the Delmarva Ultra Challenge: running a 50K before the Algonquin 50K)
After that first time on the team podium in 2021, yes, 3 with Greenbackville. After beating out GBVRC in 2021, Zach, Bri, and Jenny had become friends on the trails. Then at DUC 2023 (a crazy one), they all asked me to join the team. I was honored. I respected them all so much as runners but also as people so there was no way I could turn down the offer. I don’t exactly remember the timeline but Jenny left for Guam so they recruited Karen that year, too. Our first year together, 2023, was a great year of learning and pushing each other. Karen was nervous about running through the night, and together we all got her pumped up and she killed it! That year was a pretty even playing field with some competitive team runners. But all of us were getting some place points here and there. Zach and I are numbers people and enjoyed playing with the numbers to see how much we need to push to get place points to be the top team. We took some team laps together where of course we had the greatest laughs. And Colette was the glue that held us all together at camp. Every year our bond as a team gets stronger and it’s like a family reunion every September.

Each year the competition got tougher. In 2024, those young fast marathoner boys gave us a run for money gaining all the place points almost every lap. Zach and I mathed it early on and knew our team’s resilience was going to be overcome by speed. That’s the thing about our team. Every one of us does all 24 laps. And I can always count on them all to do that. They are some of the strongest and kindest people I’ve ever met. All of us have a few things in common with one another but as a team we all have one very big thing in common: grit. Or to be less cliche: stubbornness. Each of us has faced difficulties over the years during those 24 hours -ankles, feet, legs, stomachs, falls – but no matter what our stubbornness pulls through and we are out there every hour. In both 2023 and 2024 our mathing told me I needed more and more place points. I pushed hard both years and my team was amazing with encouraging me, yet also keeping me in check. They made sure I ate enough, my spirits were in the right place, and I was having fun. Last year might have been our team’s last hura… might. Remember that stubborn thing I mentioned?  

If it was retirement year, next year we will all still be at our family reunion Pemberton 24, just in a different capacity. Team on paper or not, we will all always be family. And as all families do, it isn’t just the 4 of us on paper. It’s our extensions, our support, and of course all the families around us. No matter what next year brings, Zach, Bri, Karen, Colette, Nate and I will always be bound together through Pemberton.

I peeked at Ultrasignup and you have a full year planned, from 10 milers to 100 milers. How do you choose your races? What other events are you thinking about?
Yes, 2026 is going to be epic. My calendar filled up very fast. One that doesn’t show in Ultrasignup is the big one: Quebec Mega Trail 135k on July 3. I had hopes of going out west this summer for a 100 miler but I’m putting that off one more year (race and travel cost add up too fast). 

I put a lot into choosing my races: First, I am working on running a race (marathon distance or longer) in every state. Each year I try to knock off 3, one local/driving distance, one a short/cheap flight away, and one a bigger trip.  

Second, the challenge. I’m constantly looking for the next big challenge for myself.  Stretching my limits, testing my grit. I have no doubt I can do any distance; it’s the terrain that gets me – the climbing, the rocks slipping from under my feet, the conditions.  

Third, the timing. I try to space out travel around work and my kids’ schedule. And of course, I make it a point to pencil in my favorite ALQ events with the people who made me fall in love with trail running. 

You’ve had a lot of success in running and racing. Have you faced challenges along the way?
The challenges are what makes it fun. I have uncovered many weaknesses over the years, mainly my hips. There has definitely been a lot of pushing too hard and having to learn to rest, recover, and strength train. When I first started running trails, I had horrible footwork…I fell a lot. I took some pretty terrible tumbles, ripping holes in a lot of clothes, scratching and bruising myself bad, breaking phones, but every fall was a lesson: slow down, pick up your feet, stop daydreaming! Ultimately, I went back to old softball quick-feet drills, jumped rope, worked on stability stuff, and of course: ran more trails. And then, there were the hills… as a flatlander: hills are hard. 

My first rude awakening of this was at 2024 Rim to River, when the hills literally put me to sleep. Yes, I fell asleep on the trail, passed out from lack of calories. I didn’t realize how much more food the hills need. But I ate and kept hilling…my legs were torn up that race, by the end I was sitting on my butt to get down the hills. After recovering, I ran more hills, trained all different ways and took on Eastern States. All the challenges I face just give me things to work on, things to find success in. All of my successes come from overcoming challenges, if not physical then mental. Every race is a personal challenge won. The speed work I did last fall brought me to successfully breaking through my mental barrier of running fast and I qualified for Boston with over 5 minutes to spare! The only challenge I haven’t directly approached with workout plans and practice is broken bones. However, I did approach them with mental strength, maybe a little stubbornness, and overcame them in stride. I broke my foot in 2021 in the middle of a race, and finished the 13 more miles. I did have to take time off running for that one, but in the meantime, I did a lot of upper body strength training, focused my diet on more bone health food and worked on my mindset. Last May, two days before the Ripper I broke my baby toe, luckily for that one my grit and mindset got me through and I pushed through the pain for the race. Then I took a few weeks off to let it heal, some. I have learned to listen to my body and know that nutrition and rest is almost as important as hard work, so any challenge can be overcome. 

What has running taught you?
Everything. I seriously mean that. One day I will write a book about all the analogies that I have learned while running, or come up with, while running. Everywhere from understanding heartbreak as the way the snow melts to understanding life’s challenges as a leaf-covered trail that we don’t ever really know which step is going to be the best. Running has taught me the little lessons and big lessons. From how scary foxes sound at night to how amazing the human body is, and how it is capable of way more than most people will ever know. Most people will never use it to even half of its capacity and will never see half the beauty this world has to offer. But I guess if I had to highlight one thing it would be that running has taught me that I still have so much to learn.  At least once a week, running helps me get through something stressful. At least once a month running shows me there is more to see, more to consider. Running is always teaching me to see the world differently and never accept things as simply what they may seem.