How Tom’s Dogs Really Got Started
The short version is simple. I love dogs. I started walking them. Eventually I built a business around that.
The real story is a little more complicated.
It begins in September of 2023. At the time I was working two jobs. During the day I walked dogs for a local pet sitting company here in southeastern Connecticut. My shift ran from 8 in the morning until about 1 in the afternoon. After that I would head home, regroup for a moment, and then start my second job.
From 2 in the afternoon until 10 at night I worked as an Analyst at Finalsite, a company that provides website systems for schools.
Most days looked exactly the same. A few hours on the road with dogs, followed by a long stretch behind a computer screen answering tickets and solving technical problems.
It was exhausting at times, but it also gave me something unexpected. For the first time in years I was spending real time outside during the day.
And I was working with dogs.
That part changed everything.
The First Walk That Stuck With Me
One of the earliest walks I remember happened on a stormy day not long after I started. The dog had never met me before and my employer warned me ahead of time that he did not like men.
The weather was miserable and the dog was clearly unsure about the situation. Instead of pushing him, I simply waited and let him watch me for a bit.
After a few minutes the tension started to soften. He stepped closer. A few moments later we were walking together.
It was a small moment, but it stayed with me.
That walk was one of the first times I realized how much dogs communicate without making a sound. The way they hold their posture. How they shift their weight. The way they scan their surroundings or glance back at you.
If you slow down and pay attention, they are constantly telling you how they feel.
I started describing it as learning to hear dogs talk. Not in a mystical sense, but simply paying attention to what they are already communicating.
The more dogs I worked with, the clearer those signals became.
Discovering Pack Hiking at Griswold Preserve
Very early on I started experimenting with small group hikes instead of simple neighborhood walks.
Some of the first pack style hikes happened at the Griswold Preserve in Old Lyme. It is a beautiful loop trail with a small waterfall and mostly flat terrain, with the option to add hills when the dogs have extra energy.
Those early hikes included three dogs named Blanche, Emmett, and Scully (tax attached).
Blanche stands out in particular. She was older and slower when we started, and I was not sure how she would handle the terrain. Within a few months something shifted. Her physical health improved rapidly. She started running. She would zoom through the trails like a puppy, her whole body lit up with energy that had not been there before.
Watching that happen was one of the first times I really understood what consistent outdoor movement could do for a dog.
That little group became the foundation for everything that followed.
Watching dogs move together through natural terrain is completely different from walking them individually down a sidewalk. The environment engages them. The pack structure gives them confidence. The movement is steady and purposeful.
The dogs came home calmer and more satisfied than they ever did from short walks around the block.
That was when I started to realize there might be something special about this style of care.
Life Between Two Jobs
For a long time I lived between those two worlds.
My mornings were spent hiking trails and managing groups of dogs. My afternoons and evenings were spent behind a laptop solving technical problems and answering support tickets.
Some nights I finished my Finalsite shift at 10pm feeling mentally drained but physically restless. Other days I was out walking dogs with a headlamp after dark before heading home to log in for work.
It was a demanding schedule, but something about it felt right.
The more time I spent working with dogs, the more natural the work felt. I started recognizing patterns in behavior, learning how group dynamics worked, and developing a rhythm with the animals.
Without realizing it at the time, those months were quietly shaping the philosophy that would later define Tom’s Dogs.
When Zoey Joined the Pack
For the first year of walking dogs professionally, Zoey stayed home.
Eventually that changed.
About six months in I began sneaking her onto a few walks with me. It was not exactly official at first. Sometimes it is easier to ask for forgiveness than permission.
After about a year working with the company, Zoey was fully integrated with most of my regular visits with approval.
Her impact was immediate.
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Zoey has a steady temperament and a calm confidence on the trail. She moves naturally through the group and tends to set the tone for the other dogs. Over time I noticed that when Zoey was present, new dogs relaxed faster and the overall energy of the pack stayed balanced.
Clients eventually started referring to her as the “pack glue.”
The name stuck because it was true.
The Moment Everything Changed
Eventually my time with that company came to an end. The circumstances were difficult, and the way things finished was not something I had anticipated.
What surprised me most was what happened next.
Several clients reached out and asked if they could continue working with me independently. They trusted the relationship we had built and did not want to lose the routine their dogs had come to love.
That moment made something clear.
This work mattered to people.
As 2025 began, I decided to take the leap and start building something of my own.
Tom’s Dogs was born.
The Early Growth of Tom’s Dogs
At first everything felt uncertain.
I had a handful of loyal clients and a strong belief that structured pack hiking could offer something different for dogs in southeastern Connecticut.
I ran my first advertisement shortly after making my decision to leave Finalsite up in Vermont, visiting Dog Mountain (if you haven’t been, you should go). The response was better than I expected and it gave me the confidence to keep building.
The work grew steadily. More dogs joined the hikes. More families trusted me with their pets. The days became longer and fuller.
Some of those dogs arrived with real challenges. Wiggins had surgery on both hind legs. He was not fully stable when we started hiking together. Today he is one of the best hikers in the pack — steady, focused, and one of the most well-behaved dogs I work with. Louise could barely crack one mile per hour when she first joined. She simply did not have it in her to go any quicker. A few months later she was running with the rest of the pack.
Those transformations did not happen by accident. They happened because the work is consistent, and because the trail gives dogs something to rise to.
Eventually Tom’s Dogs officially became Tom’s Dogs LLC on September 14, 2025.
Where Things Stand Today
Today Tom’s Dogs works with more than thirty dog families across New London County and the surrounding communities.
On lighter days I might see five dogs between a pack hike and a few individual walks. On busier days it is not uncommon for that number to reach ten or more across hikes, walks, and pet sitting visits, for days (or weeks!) in a row.
Some days include several hikes. Other days involve overnight stays with dogs while still running the regular hiking schedule.
It is demanding work, but it is also deeply rewarding.
Every wagging tail and every relaxed dog at the end of a hike reminds me why I chose this path.
Why I Would Do It All Over Again
Starting Tom’s Dogs meant throwing myself into the deep end.
And I mean that more literally than it might sound.
I have been bitten twice. The first time a Cane Corso got me. I took two days off and went back to work. The second time was a few months ago. I did not take any days off.
One morning my car broke down on the way to Wiggins. I got out and walked the rest of the way to his home on foot to make sure he got his walk in. It turned out his dad was home when I arrived. We had a good laugh about it.
That is the job.
Some days are hard in ways you do not expect. But you show up because the dogs are counting on you and the families trust you with something they love. That does not stop mattering just because the morning got difficult.
Everything was a challenge in the beginning. Scheduling. Weather. Managing pack dynamics. Learning how to grow responsibly while still giving every dog the attention they deserve.
But every single day brought another lesson. Every hike taught me something new. Every dog had a personality to understand. Every small success built confidence.
What started as a way to escape a desk job slowly turned into something much bigger.
It became a way to build a life that feels real. A life spent outside, moving through the woods with a pack of happy dogs.
Looking back now, choosing to follow that path was one of the best decisions I have ever made.
And if I had the chance to do it all again, I would not change a thing.
Tom Grylka is the founder of Tom’s Dogs LLC, a professional dog walking and pack hiking service serving New London County and southeastern Connecticut.
Learn more at tomsdogs.com
