Paul Holloway Memorial book

PAUL E. HOLLOWAY I N

L O V I N G

M E M O R Y

JUNE 17, 1976-JULY 25, 2025

LARGER THAN LIFE: MEET PAUL E. HOLLOWAY

If you’re holding this magazine, chances are you already know Paul. Or maybe you felt like you did—even if you only met him once. That was his magic. Paul didn’t just enter a room, he owned it. Not in a loud, look-at-me kind of way—but with warmth, humor, and a magnetism that made you feel like you were the most important person in the world. If you needed help, he was already there. If you were down, he had a story, a hug, or a harmonica solo ready. And if there was music playing, well, chances are he was halfway through a blues riff before you realized he brought the band with him.

Born on June 17, 1976 in Ware, Massachusetts, Paul—the proud son of Bruce and Jeanne Holloway—filled his 49 years with more energy, laughter, and connection than most people do in a century.

He lived a life of “yes.” Yes to helping. Yes to adventures. Yes to being the first one in and the last one standing. Whether you called him son, brother, husband, teacher, coach, co-worker, or friend, you knew: Paul was one of one.

He was a proud graduate of Quabbin Regional High School (Class of ‘94), earned his bachelor’s degree from Fitchburg State in ‘98, and later a master’s from Bay Path University. But ask anyone what Paul really mastered in life, and they’ll tell you: connection. Kindness. Service. And making every moment matter.

For 14 years, Paul taught at Palmer High School as a special education teacher. He spearheaded the launch of Unified Sports programs like Basketball and Track & Field, along with a cooking class that brought students together in the most nourishing way possible. His goal was simple but powerful: make sure every student had a place to belong and feel valued. He brought special education and general education students together in ways that transformed the school culture—creating teams, classrooms, and friendships that transcended any label.

HE LIVED A LIFE OF “YES.” YES TO HELPING. YES TO ADVENTURES. YES TO BEING THE FIRST ONE IN AND THE LAST ONE STANDING.

And it didn’t stop when the school bell rang. Paul was always working behind the scenes—organizing fundraisers, seeking out resources, doing whatever it took to give his students the extras they deserved. Field trips, gear, experiences—they weren’t just nice-to-haves. To Paul, they were musts, because his students mattered. And he made sure they knew it.

When Paul wasn’t in the classroom, he was building something— figuratively and literally. A 25-year veteran of the Holloway Painting Company, he brightened homes and businesses with his skill and unmatched work ethic. And starting in 2022, he proudly served as a volunteer firefighter with the Holland Fire Department, answering the call when his community needed him.

PAUL HAD A WAY OF MAKING ORDINARY MOMENTS FEEL EXTRAORDINARY Still, he found time to sling pints at Vanished Valley Brewing Company, play harmonica with friends or complete strangers, and—true to form—show up to help someone stain a porch, move a couch, or build a fire pit… often without being asked. Paul believed in showing up, staying late, and laughing through the chaos.

At events like the MOORE Expo and Big Iron Overland Rally, Paul wasn’t just a helping hand—he was the backbone. He helped his little brother, Chris, turn these ideas into reality, never hesitating to dive into the chaos, haul gear before sunrise, keep the team grounded, and make the impossible feel doable. His presence shaped the soul of both events. They were built on community, connection, and heart—exactly what Paul brought into every room he ever entered.

And behind the scenes, Paul’s role as a big brother was one he took to heart. He was endlessly proud of his sister Stacey, never missing an opportunity to remind others—and her—how much potential he saw in her. He believed in her, supported her, and loved her fiercely.

Whether cheering her on quietly or offering a muchneeded boost when things got tough, Paul was Stacey’s biggest fan. Their bond was deep and lifelong, rooted in encouragement, laughter, and unconditional love.

TOGETHER, THEY BUILT A LIFE FULL OF HUMOR, ADVENTURE, AND GENUINE COMPANIONSHIP. And then, there’s the love story. Paul and Kristina weren’t just partners—they were home to one another.

From the first time he talked about her, you could tell: this was it. That spark in his eyes. That proud grin. He had found his person, and he knew how lucky he was.

Together, they built a life full of humor, adventure, and genuine companionship. They cooked together, supported each other’s passions, and turned everyday moments into a love story that inspired everyone around them.

Paul once said, “If I had my life to live over again, I would find you sooner so that I could love you longer.” And if you ever saw them together, you know—that wasn’t just a line. That was the truth. Their love was rare. Easy, grounded, joyful, real. They were better together. And Paul knew it—and made sure Kristina knew it, every day.

So what is this magazine really about? It’s not just about saying goodbye. It’s about saying thank you. Thank you to a man who gave everything to everyone, without ever asking for credit. Thank you to the harmonica-playing, disc golf-slinging, soul-hugging, fire pit-building friend who made us feel like we mattered. Thank you to Paul.

This issue is filled with moments and memories from the lives he touched—and there are so many. Stories from his students. Laughs from his closest friends. Tales of kindness and chaos. Because Paul didn’t just leave behind a legacy—he left behind a movement. One built on showing up, helping out, lifting spirits, and living big.

THANK YOU TO THE HARMONICAPLAYING, DISC GOLF-SLINGING, SOUL-HUGGING, FIRE PITBUILDING FRIEND WHO MADE US FEEL LIKE WE MATTERED. THANK YOU TO PAUL. And that’s why the Paul Holloway Memorial Giving Fund exists—to continue what he started. Founded by Kristina, this fund will support the inclusive programs Paul was so passionate about—like Unified Sports, classroom enrichment, and experiences that help students feel seen and supported. Every dollar donated helps keep Paul’s work alive for generations of kids to come.

So read these pages. Share the laughs. Feel the impact.

And when you’re done, go out and do something Paul would’ve done: Help a neighbor. Make someone laugh. Wear the damn sneakers. And love people like it’s your job.

Live louder. Hug longer. Give more. And always—always —#LoveLikePaul.

#LOVELIKEPAUL

“THE MOMENT I KNEW”

By Kristina Dobiecki Holloway

I remember the first time I saw Paul.

It was the start of a new school year at Palmer High. All staff had returned for meetings. I was heading to the auditorium, rounding a corner in the lobby—and there he was. Talking and laughing, completely unaware that he’d just changed the course of my life.

I stopped in my tracks, turned to a colleague and whispered, “Who’s that?” She replied, “That’s Paul Holloway. He’s new. I think he’s dating someone here.” So I smiled, nodded, and tucked that moment away.

What none of us knew then was that Paul’s new classroom, room 317, had the perfect view of my office window. And taped to my window, still hanging from the year before, was a sign that read: HELLO ROOM 317.

Paul thought it was a welcome note just for him.

On his lunch break one day, he called to say hello and thanks for the sign. Confused at first, I then remembered the old sign and awkwardly explained that it was from last year. He probably turned bright red—but it was the first of many laughs between us.

We were friendly colleagues for eight years. Timing never quite aligned. We were both navigating life and other relationships. And then, at an end-of-year pool party in 2019, somewhere between floating in the water and a round of yard games, Paul asked me out.

My mind screamed “ohmygod, ohmygod, ohmygod!” and then I casually replied “Yeah! That’d be fun.”

THAT FIRST DATE LASTED SEVEN HOURS.

That first date lasted seven hours.

We connected instantly and authentically. He was kind, funny, open, and made me feel so comfortable around him. On the third date, at the beach, Paul declared that he wasn’t interested in seeing other people. I agreed, and we made it official.

We filled the next few years with concerts, beach days, road trips, meeting & loving each other’s family and friends, and lots and lots of laughter. When Covid hit, and the world shut down, Paul and I decided to stick together. Those types of together 24/7 situations can often make or break a relationship. We were thrilled that it made ours stronger. We cooked corned beef, planted hot pepper seeds, tried to learn Heart of Gold and What’s Up on the guitar, and went on a hike everyday to a new spot.

And then, one summer day off the coast of Hyannis, in the middle of the ocean, Paul asked me to marry him.

With his Grandma Alice’s ring.

Right there in the waves, one hour into our week-long vacation.

He said he couldn’t wait.

It was bold (a little risky), and completely perfect.

I said yes before he could drop the ring in the water.

Later, when we told my dad the news, my dad got choked up and said, “I don’t know if he’s the man of your dreams… but he’s the man of mine!” That’s how you knew you found a good one.

When we stood together on our wedding day, hand in hand, I remember thinking: This man- this loving, open, fun, kind-hearted man- is my future. We danced to the two truest lyrics: It’s always better when we’re together, and how wonderful life is while you’re in the world.

I didn’t just marry Paul.

I married my best friend.

And even now, heartbroken in this unimaginable grief, I hold onto the fact that it was real, true love that we shared. Not just the image on social media (though we all know Paul loved to post our adventures on Facebook!) It was a love that lived in laughter, understanding, and connection. And that just a week before he passed, Paul said “We’ve got a great life, don’t we?” and I smiled and said “We do.”

Paul, thank you for loving me, for choosing me, and for giving me a wonderful life. I am so grateful to be your wife.

The best parts of you will live on, and I will carry them forward for both of us.

I love you forever.

— Kristina

I DIDN’T JUST MARRY PAUL. I MARRIED MY BEST FRIEND.

“I DROVE A ZAMBONI ONCE”

A job interview. A one-liner. A lifelong friendship.

Back in the early 2000s, Paul and his buddy Stuie found themselves in Scottsdale, Arizona, wandering into a nightclub they’d visited the night before—this time, looking for a lost wallet. They didn’t find the wallet, but they found something else entirely.

They struck up a conversation with the club’s general manager, who’d just fired his entire staff the night before (as one does in nightclub management). The guy needed help—fast. So he asked the two fresh-faced, heavy-accented Massachusetts boys a simple question: “Do you have any experience working in bars?”

Paul didn’t hesitate. He looked the manager dead in the eye and said, “No, but I drove a Zamboni once.”

THAT QUICK WIT AND FEARLESS CHARM? IT WASN’T JUST A FUNNY MOMENT—IT WAS PAUL IN A NUTSHELL.

That was it. No résumé. No follow-up explanation. Just Paul being Paul—charming, bold, hilarious, and impossible not to like. The GM burst out laughing. Hired them both on the spot.

That quick wit and fearless charm? It wasn’t just a funny moment—it was Paul in a nutshell. He didn’t need credentials to make an impression. He showed up, took the pressure out of the room, and turned strangers into lifelong friends.

That Scottsdale job led to a 24-year friendship, countless memories, and—of course—many, many more stories. But it all started with a Zamboni. And if you knew Paul… it somehow makes perfect sense.

Jeanne Holloway Paul and his mom, Jeanne Holloway, were a team. Through many hurdles as a child and every season after, he stood by her and championed her. They talked often—honest, thoughtful conversations that showed how close they were. Their shared love and kindness towards others ran deep, and it shaped the way Paul cared for everyone around him.

Bruce Holloway Paul learned a lot from his dad, Bruce Holloway. He kept Bruce’s Veterans Day tradition alive at the school, organizing the program each year because it mattered to them both. Paul’s steady work ethic, easy charm, and love of music were things that made his dad proud—and made Bruce’s influence clear in the way Paul lived and led.

“JUST BE YOU” How Mr. Holloway Helped Me Shine at Prom As told by Taelynne McCloskey High school prom is supposed to be a magical night—but for me, it didn’t feel that way at first. I didn’t want to wear a dress. It just wasn’t me. I started thinking maybe I shouldn’t even go. But then Mr. Holloway stepped in.

He always knew how to make people feel better. He understood me—not just as a student, but as a person. He knew my family—my two sisters included—and how I was the quieter one. He used to tease me and say, “Be more like your sisters!” and then quickly follow it up with a warm laugh and, “I’m just kidding, Taelynne. It’s okay to be yourself. You’re unique… just like your name.”

Those words stuck with me. So when I told him I didn’t want to go to prom because I hated dresses, he didn’t try to talk me out of it.

Instead, he lit up and said: “Let’s wear matching Converse.”

That changed everything.

On prom night, I wore what felt right for me—with my favorite Converse shoes. So did he. And I didn’t feel awkward or out of place. I felt proud. And then came the photo booth.

That’s where one of my favorite memories happened.

Mr. Holloway put on a giant Viking helmet, grabbed a huge rubber chicken, and struck a ridiculous pose. I threw on oversized sunglasses and grinned from ear to ear. We took the goofiest, happiest pictures—and in that moment, I felt like the truest version of myself.

MR. HOLLOWAY DIDN’T JUST HELP ME THROUGH SCHOOL—HE HELPED ME BELIEVE IN MYSELF. He made it fun to be me.

Mr. Holloway didn’t just help me through school—he helped me believe in myself. I still think about his words when people compare me to others. He reminded me that being different isn’t something to hide. It’s something to celebrate.

And just like my name, he made me feel one-of-a-kind.

HE WOULD’VE LAUGHED AT THIS We all know Paul wouldn’t want anyone sitting around feeling sorry for themselves. He’d crack a joke, roll his eyes at a mushy quote, and say, “Alright, that’s enough of that.”

In honor of the man who could get a laugh out of anyone—even a smoke alarm going off mid-cooking class—we present the tribute Paul probably would’ve written himself…if he weren’t too busy planning his next big adventure.

If Paul Wrote His Own Obituary…

Paul Holloway, 49, made his final entrance by sliding into Heaven on a Zamboni, Viking helmet on, shrimp skewer in hand, headed straight for the grill. He was greeted by his late father with a celestial blues jam and a cold beer—ice still clinging to the rim.

He leaves behind an entire community of people who will keep telling his stories—each time a little louder, a little funnier, and a little more Paul than the last.

He kindly requests that in lieu of flowers, you: Buy a non-working boat, a bike you’ll never fix, and a golf cart with questionable wiring Skip the dress shoes—life’s too short to be uncomfortable, especially if there’s dancing involved Help your neighbor whether they like it or not Tip the bartender. Help the underdog. Call your sibling.

And for the love of God—let’s spend the day at Hampton soon!

If you ever feel down, he’d remind you: ““Life is not measured by the number of breaths we take, but by the moments that take our breath away.” — Maya Angelou” His final words were likely: “And that’s how it’s done” Heaven’s been louder, brighter, and way more fun ever since.

HONORING HIS SERVICE Holland Fire Department – Firefighter Paul Holloway

“He didn’t wear it for recognition—he wore it because he cared.”

“PAUL PROUDLY SERVED THE HOLLAND FIRE DEPARTMENT WITH HONOR, HEART, AND HUMILITY. THIS BADGE REPRESENTS HIS SELFLESSNESS AND DEDICATION TO PROTECTING HIS COMMUNITY.”

Firefighters Prayer: When I am called to duty, God wherever flames may rage, give me strength to save a life, whatever be its age.

Help me to embrace a little child before it's too late, or save an older person from the horror of that fate.

Enable me to be alert to hear the weakest shout, and quickly and efficiently to put the fire out.

I want to fill my calling and to give the best in me, to guard my neighbor and protect his property.

And if according to your will I have to lose my life, bless with your protecting hand my loving family from strife.

CARRY IT FORWARD: PAUL’S LIVING LEGACY Paul Holloway lived with intention, humor, and an unmatched ability to make others feel valued. Whether coaching a team, answering a fire call, mentoring a student, or showing up for a friend—he made his corner of the world better.

And now, we can do the same in his honor.

The Paul Holloway Memorial Giving Fund Created by his loving wife, Kristina Dobiecki Holloway, this fund was established to keep Paul’s spirit of generosity and community alive. It will help support the kinds of programs and initiatives that reflect what Paul cared about most—people.

From helping students feel included and supported, to fueling joyful experiences and random acts of kindness, this fund will continue to uplift lives in meaningful ways.

THAT’S HOW LEGACIES LIVE ON —WHEN WE CARRY THE BEST PARTS OF SOMEONE FORWARD INTO THE WORLD AROUND US. The Paul Holloway Effect We invite you to honor Paul not just with a memory—but with action.

Choose one or more of these in his name: Volunteer for something that matters Help a neighbor without being asked Learn something new—just for fun Tell a joke that will make someone smile Show up for someone who needs you

✅ ✅ ✅ ✅ ✅

Then say, “This one’s for Paul.”

To contribute or learn more about the Paul Holloway Memorial Giving Fund, scan the QR code to the right.

Because that’s how legacies live on—when we carry the best parts of someone forward into the world around us.

A LEGEND SIGNS OFF He didn’t enter a room quietly.

He didn’t leave one unnoticed.

Paul had a way of filling space—not with volume, but with presence. With purpose.

He remembered names.

He fixed things no one else noticed were broken.

He brought people together in ways that never felt forced.

And if you were lucky enough to be part of his circle, you didn’t stay on the edge for long—he’d pull you right into the center.

He built fires, cracked jokes, coached teams, hauled gear, answered calls, and never waited to be asked.

He taught by doing. Led by showing up.

And somehow—no matter how much he gave—he always had more to offer.

The truth is, we thought we had time.

More projects, more parties, more track meets, more shrimp on the grill.

But time, it turns out, doesn’t consult us.

So we’re left with what he gave us: A louder laugh.

A better playlist.

A deeper sense of what it means to belong.

And a reminder that the good ones never really leave.

They just stop knocking.

And start showing up in other ways.

A harmonica riff.

A flash of LED light.

A smoke alarm during dinner.

We’ll catch ourselves smiling at nothing.

And we’ll know exactly who it was.

Because legends don’t end.

They echo.

“Life is not measured by the number of breaths we take, but by the moments that take our breath away.” — Maya Angelou — The Holloway Family

Dear Father in heaven, We give you thanks for blessing us with Paul’s life.

Thank you for the time that we each had with him.

Paul shared his love to any and all.

His kindness, generosity, ability to share joy and happiness is an example that will be in our hearts forever.

We know that Paul is giving You a big bear hug, along with a hearty laugh and that he is safe and loved… ...until we meet again.

-Kristina, Mom, Stacey, Chris, Megan and Rowyn

IF I HAD MY LIFE TO LIVE OVER AGAIN, I WOULD FIND YOU SOONER SO THAT I COULD LOVE YOU LONGER.