If there’s one thing Dana Searcy knows about his best friend, it is this: There is no quit in Damien Booker.

That much was clear midway through the 2023 Womp Romp 10-mile trail race at Wompatuck State Park in Hingham, Mass. It was Booker’s first trail race. His knees ached and his lungs throbbed, the result of a two-week battle with illness prior to race day that sapped his strength and energy, but not his willpower. Despite his body’s wishes, he and Searcy ran every step of the race together on the rolling trails through the 3,500-acre forest. It was chilly and a light rain fell as they emerged from the woods and the finish line came into view a quarter-mile away.

Booker’s face bore a pained grimace, but it transitioned to a smile and his eyes lit up with 100 meters to go. Alongside him, Searcy grinned from ear to ear. Moments later they were done.

“I went right to the car,” Booker recalled. “I was thankful that I had access to Dana’s car, and I was able to unlock the car and sit down. I had no desire to talk to anyone. My knees were killing me and I had to go sit down.”

Searcy was proud of his friend for persevering. He saw the grit and determination he has come to know from Booker during nearly 25 years of friendship. But he also saw something else in Booker: potential.

“I realized that Damien has the right mentality for doing races like this,” Searcy said. “Because the first thing he said was ‘I signed up for this; I’m getting it done.’ That meant that even if I struggle, I’ll do whatever it takes; it’s going to get done.

“And I realized you know what? He’s got the right mentality …,” Searcy said, pausing to chuckle before adding, “…so, for his birthday, I’m going to sign him up for the 50K.”

Miles on Motorcycles

Booker and Searcy are no strangers to logging miles together; they’ve been doing it for years, just not always as runners.

Though they didn’t know each other until adulthood, both men grew up and played sports in Boston. Booker enjoyed baseball and soccer, and played hockey through his sophomore year of high school. Searcy played little league baseball, basketball and football. Both attended college in Atlanta before moving back to Boston in the late 1990s. Their paths finally crossed in 2000 or 2001 when a mutual friend – restaurateur Boyce Slayman – introduced them.

“We became tight just from hanging out with each other,” Searcy said.

They shared a particular passion for motorcycles. Booker rode a Honda CBR600 and Searcy a Honda CBR900 before both later switched to Honda CBR954rr sportbikes. Together with Slayman, they spent countless hours cruising all through Boston.

“We didn’t ride with a motorcycle club,” Searcy said, “but we had our own little club with bikes, just the three of us.”

After several years of motoring through the miles on the road, their interests and lifestyles evolved. Fatherhood came calling, first for Booker and later for Searcy. They traded their motorcycles for sneakers and started running road 5Ks occasionally, including the Susan B. Komen Race for the Cure and the Cambridge Classic.

Eventually, Searcy turned to cycling as a new challenge, and greater endurance feats soon followed. A coworker encouraged him to run a half marathon, so he signed up and ran Boston’s Run to Remember in 2007.

“I ran it in honor of my mother and father who passed away from cancer,” he said. “That was the real motivation and inspiration to make me push through those times that got kind of challenging. Having that motivation made me realize that the body is much more capable than the mind is. The mind understands that I’m tired and want to give up, but the body can keep going. I realized that because I was exhausted one day and I thought to myself, if my mother and father could fight cancer, I can finish this run. I’m going to finish or I’m going to drop, and I never dropped. I was exhausted, but I didn’t drop.”

Searcy persevered and finished in 1:58:04. After the race, he was eager to take on his next endurance challenge, so his coworker and her husband invited him to train with them for the Cranberry TriFest triathlon. Searcy completed the sprint distance, and competed in a few more triathlons before the birth of his daughter necessitated that he dial back his racing for a few years.

Transitioning to Trails

Though both men occasionally ran in the years that followed, Searcy began dabbling in trail-running in 2021. In 2022, another of his Cambridge Public Schools co-workers, experienced ultrarunner Jesse Rebecca Jackson, challenged him to sign up for a 50K trail ultramarathon.

“I was like ‘what, are you nuts?’” Searcy recalled with a laugh. “But she gave me this book to read, Born to Run, and after reading that book I was like ‘sign me up!’ because I was so inspired by it.”

Together, Jackson and Searcy registered for the Womp Romp 50K and began training together by running home after work. In February, Jackson invited Searcy to join her for group runs with the Trail Animals Running Club (TARC) at the Blue Hills Reservation in Milton. By race day on October 22, Searcy was over-prepared and nervous, with a bulky running backpack loaded with supplies.

“I didn’t know what to expect,” he admitted. “I was doing what I thought I was supposed to do. But when we actually did the race I felt a lot better than I expected, I think mainly because I slowed my pace down a little bit. I was thinking about it in terms of running half marathons; if you run a half marathon on the road you’re constantly running, but with the ultra you can run, you can walk, you can stop at the aid stations, talk to people and socialize, and then get back on the trails. I think experiencing that made me realize, ok, I’m actually having some fun, although it’s still challenging. But I felt a lot better than I expected.”

Thanks to Jackson’s support and guidance, Searcy finished the race in 7:04:06 and officially became an ultrarunner. He felt satisfied and content, having lived his own Born to Run experience.

“I thought I would still run the trails,” Searcy said, “but I wasn’t really hungry to do another one… until I talked Damien into signing up for the 10-miler.”

Sharing the Experience

Just like she did for Searcy, Jackson showed Booker around the local trails for some of his initial runs. Then Searcy brought Booker to a group run at the Blue Hills that proved to be an eye-opening experience. For his first group run, Searcy had Booker go with a small group that completed a 4.7-mile loop with around 500 feet of elevation gain on rocky, rooty terrain.

“He’s trying to kill me!” Booker joked about the experience. “I thought, ‘it’s not fun, but let’s do it.’ I don’t mind taking my time; I’ll get it done.”

Indeed he did, and Booker returned with Searcy the following month to run the trails again, this time joining another group for a 6-mile loop on trails and rolling fire roads. The more Booker ran the trails, the more he discovered he liked them.

“Trail-running takes my mind off the distance, so to me I enjoy the trails more,” he said. “It’s not about the landscape or anything like that; it just takes my mind off the mileage because I have the potential of breaking my neck so I have to focus, and the next thing you know the miles are already done.”

Though his preparation for the Womp Romp 10-miler was upended by an illness, Booker ultimately completed the race on October 21, 2023. Searcy was right by his side for every step.

“Twenty years ago we were riding motorcycles,” Booker noted. “And now we’re running trails.”

An Ultramarathon Adventure

In hindsight, Booker admits he should have known something was afoot given the unusual questions he was peppered with by Searcy.

What’s your address? What about your email address? Who’s your cell phone provider? What size T-shirt do you wear?

“He’s asking me questions that… I wasn’t quite sure, like, what the hell are you talking about?” Booker says with a laugh, shaking his head at the memory. “But I probably should have known.”

They were hanging out at Searcy’s house on December 14, 2023, celebrating Booker’s 48th birthday. Searcy, 51, had been plotting this moment ever since the conclusion of the 10-mile trail race 7 1/2 weeks earlier. Each question led him one step closer to completing Booker’s birthday present. Once the answers were sufficient, Searcy snapped a screenshot and texted it to Booker.

“I said, ‘Damien, happy birthday,’” Searcy recalled. “His phone went off, he looked at it, and he went ‘What the hell?’”

Booker was one of the earliest entrants into the 2024 Womp Romp 50K.

“And then he tells me ‘yeah, I’ll sign up eventually,’” Booker said. “I think he probably signed up 6-8 months later. I was signed up so I was going to do it, even if he didn’t do it.”

That reaction is precisely why Searcy knew Booker needed to run an ultra.

“That’s what I’m talking about; he’s got that mentality that if I’m signed up, I’m committed to it and it’s going to get done,” Searcy said. “That’s the mentality you have to have out there; it’s like ‘I’m not going to let these trails defeat me.’”

Searcy spent the first few months of 2024 training for his first Boston Marathon, which he completed in April while raising money to support Boston Medical Center. After that, he and Booker began preparing for the ultra. Searcy mapped out a plan for the men to complete short runs during the week and longer runs on the weekend. Though they didn’t follow it rigorously, they put in trail miles running loops of the Blue Hills’ 6-mile White Dot Loop and made it to the starting line on October 26 healthy and ready to run three 10+-mile loops at Wompatuck State Park.

Managing the Miles

The trails were dry on race day, and it was sunny with temperatures in the 50s and 60s. Both men wore shorts, short sleeves and caps. Other than a few snacks tucked in their pockets, they kept their loads light.

As they clicked away the miles during the first and second loops, they chatted, managed their nutrition and made steady progress. All along the way, fellow runners offered words of encouragement.

“Everyone is very nice out there on the trails cheering you on,” Booker said. “That’s a bit different, something new for me. It’s something I don’t see often. Everyone was nice; everyone seemed pleasant and cheering you on. You don’t get that often.”

Though he was running the longest race of his life, the biggest obstacle Booker encountered came from the assortment of Gu energy gels he took to supplement his nutrition. He’d purchased a mix of caffeinated and non-caffeinated gels; after taking a few of them, Booker’s stomach felt uneasy and his heart raced.

“At some point during the last loop I took another gel, and then it went downhill,” Booker recalled. “I felt like I had chest pains, so Dana’s like ‘whoa, whoa, whoa! Let’s walk for a bit.’ We ended up walking for quite awhile.”

Despite the adverse reaction to the caffeine, Booker had no intention of stopping until he reached the finish line. He had his best friend by his side, and they’d get it done together, no matter how long it took.

“I felt like my job was to keep him motivated, keep the conversation going, and keep him putting one foot in front of the other,” Searcy said. “I think the motivation was that, as you know, there are not many people of color who are out there doing this sport, and so here I have my best friend who’s doing it with me. I thought about how inspirational that will be not only from his perspective or my perspective, but from his kids’ perspective. To think that my dad has run 50K – there’s not many people who can say that.”

The only time Booker stopped was when Searcy made him, but it was for an important milestone.

“When he got to 26.2 miles, I stopped him and I congratulated him,” Searcy said. “I said ‘D, stop! Stop! And he’s like ‘What?’ I said ‘Congratulations! You just ran your first marathon! Now let’s keep going!’”

“When he got to 26.2 miles, I stopped him and I congratulated him. I said ‘D, stop! Stop!’ And he’s like ‘What?’ I said ‘Congratulations! You just ran your first marathon! Now let’s keep going!'”

Another runner passed them with a few miles to go. The caffeine finally started to wear off and Booker felt a bit better. His competitive spirit returned, so it was time to hustle.

“That’s just the competitive nature in me, because we could’ve walked it home,” Booker said. “We were on pace to walk the rest of the race until the kid came running by us, and then I was like, ‘no, we’ve gotta go! Damn the chest pains; I don’t think it’s a heart attack, so let’s go!”

Though they didn’t quite catch the other runner, they ran the final few miles and finished side by side, Booker in 8:20:41 and Searcy in 8:20:42.

Unlike the year before, Booker didn’t need to sit down immediately after finishing. Instead, he and Searcy took a few minutes to chat with Womp Romp race director Matt Hoadley, and then grabbed some food and hung out with other runners.

“The 10-mile race was more painful and grueling on me than this one,” Booker said. “This time we’re hanging out, meeting people, talking about things with folks we just met. It was a better experience this time around.”

Though he enjoyed the experience, there is one thing Booker wasn’t satisfied about: his time.

“I was already thinking about the next year … the 50K, and improving my time,” Booker said. “I’ve gotta do better next time, improve my time a bit. I was thinking we would do it in less time; I need to do better.”

Perhaps next time it’ll be Booker signing up Searcy for a race.

“After the race Damien’s like, ‘my time could have been better. We’ve definitely got to do it again next year.’ And I’m like ‘that’s not what I expected the response to be!’” Searcy said. “Now he’s talking all competitive, and he’s online looking at other races in other places and other things. So I’m thinking ‘ok, I guess I’m going to keep running then!’”

Running for the Long Term

Though Booker wants to improve his 50K time, his top priority is maximizing the health benefits and quality of life that running supports.

“I was battling high blood pressure,” he said. “They were trying to get me on high blood pressure medication; I said no. I kept telling the doctors no.”

“It’s not like I’m a die-hard runner now, but I reached out to Dana about running even after the race, so it’s definitely something we need to continue to do. It’s a health benefit. That’s my big thing; no medication for me.”

Unlike their motorcycle-riding days that were fun but ultimately left in the past, both Searcy and Booker see running as something they want to pursue for the long term. Running – and trail-running in particular – offers new challenges, opportunities and adventures that they are excited to pursue.

“At this point in my life running was the last thing that I thought I’d be doing,” Searcy said. “But I’ve actually come to enjoy it so much that I want to make sure that I run in a way that ensures that I’ll be able to run for the long haul.”

In addition to enjoying trail-running together and with the community, both men hope to one day share the trail-running experience with their children.

Booker said he doesn’t think his kids appreciate yet what it means to run a 50K, but he has an idea of how to help them visualize it. Their school is about a 15- to 20-mile drive from the Booker home.

“It’s like when we go to school and we go back home; I did that running,” Booker said he’ll tell them. “I tried to coerce one of them to go run with me and have her put in some miles; she could be a runner. It’d be interesting to get the kids out there.”

Searcy agrees. His daughter, Madison, even has a bit of trail-running experience already.

“I’m trying to get my daughter out there,” he said. “She did a summer camp last summer where they had to run 7 miles a day at 4:30 in the morning, five days a week, on the trails. I’m like ‘listen, if you can do this, you can come out with me!’ But she was like, ‘nah, I’ve gotta do it again next summer.’ I can wait.”

What’s Next?

Booker and Searcy have their sights on more trail-running adventures in 2025. They are currently 10th and 11th on the waitlist for the 15-mile night race at the TARCtic Frozen Yeti in early February at Hale Reservation in Westwood.

“It sounds like an adventure,” Searcy said of the event that has seen everything from snow and sub-zero temperatures to downright pleasant conditions. “It sounds like something really fun, with backpacks and headlamps and a mandatory blanket.”

They’re also considering the TARC To Hale and Back 6-Hour race in March, also at Hale. They might sign up for the Cambridge Classic race series, even though it’s on road. Or maybe they’ll find a destination race to travel to.

“We’ve been talking about Sedona,” Booker noted. “But we’re just looking.”

They’ve certainly come a long way from riding motorcycles to racking up miles on the trails of the greater Boston area. Wherever they decide to run next, they know they can do so in good company.

 “The most important thing I think about all of this is that I’ve enjoyed the running community, because trail-running is something that I never thought about,” Searcy said. “It never was on my radar, and then once I started doing it, it just opened up a whole new world. The thing that makes me feel really grateful about it is now I’ve got someone to do this with, and it’s my best friend.”