The Incredible Story of Baltimore Jack, King of the Appalachian Trail

Certain hiking trails stand out from the crowd, and the Appalachian Trail is most certainly one of them. Known simply as the AT to hiking enthusiasts across North America, this trail stretches some 2,200 miles in length, running from Georgia to Maine and holding the record for the longest hiking-only trail on the planet.

Baltimore Jack with his hiking gear taking a photograph on a woodsy path while holding a tree

Source: Twitter

Two million people hike at least part of the trail each year, and several hundred thru-hikers attempt to take on the entire thing each season. But there’s one particular hiker whose name has become synonymous with the Appalachian Trail. His name is Leonard Adam Tarlin, also known as Baltimore Jack, and this is his utterly incredible story.

Back to the Beginning

To truly understand the life of the man known as Baltimore Jack, we have to go back to where his story all began. Leonard Adam Tarlin was born on November 12 of 1958, in Brookline, Massachusetts, just outside of Boston. He was the youngest of four siblings, with three older sisters who helped raise him.

Baltimore Jack holding a very large rock while standing on a rocky path

Source: Flickr

From an early age, Tarlin’s incredible intelligence was evident. His sister, Erika Tarlin, recalls how he was “always the smartest kid around” and that many people were impressed by his intelligence and wit. It was clear for anyone who knew him that this kid was something special.

A Troubled Childhood

Unfortunately, Tarlin’s life didn’t get off to the best possible start. Even though he was a clever and funny boy who made friends easily, he endured some dramatic tragedies in his early years, beginning with the loss of his mother. He was just nine years old when his mom died.

Baltimore Jack leaning against a stone wall with a sign for the Appalachian trail conference behind him

Source: Imgur

Sadly, his father died seven years after that, when Tarlin was in his teens. He was actually in the final year of high school when his father passed away. It’s never easy for anyone to lose their parents, but especially not when they’re still so young and still have so much life to live and things to learn about the world. Erika remembers Tarlin struggling to cope with the passing of both parents.

A Difficult Period of Life

Anyone who has ever lost their parents will know how difficult it can be, and the losses really took their toll on Tarlin. He’d always been a cheerful, outgoing, witty sort of boy, but losing his mother and his father certainly wasn’t easy. He tried to continue living life as normal, but under the surface, he was dealing with a lot of distress and pain.

A photograph of Baltimore Jack leaning against the Appalachian trail conference sign in 1999

Source: Imgur

“I know he certainly did a lot of questioning after something traumatic like that,” explained Erika in an interview, highlighting how her brother was forced to reassess some things about the direction of his life in the wake of his father’s passing. This is a perfectly natural thing to do. A lot of kids who lose their parents end up with a different view of the world; they have to grow up and make some big decisions more quickly than their peers.

A Typical Life

In Brookline, as in many other cities across America and other parts of the world, most people follow a typical plan, according to Erika, hitting the usual beats like getting a college education and finding a partner. “Growing up where we did, you sort of follow a path of high school, college, get a job, get married, all that.”

Baltimore Jack sitting on a ledge at the Appalachian trail entrance in 1995

Source: Imgur

Since this was the common way of life for anyone growing up in the area, it seemed only natural that Tarlin and his sisters would follow that same path too. Even with the loss of their parents, they were all intelligent and well-supported by other family members and friends, with plenty of potential to grow up and succeed in their lives, despite a difficult start.

A Different Path

However, it seemed that Leonard Adam Tarlin wasn’t too interested in following that preset path. Even from an early age, he’d shown a distaste for “ordinary life” and always seemed like he wanted to do things differently from everyone else. For him, the idea of following the usual path simply wasn’t too appealing.

Baltimore Jack standing against the wall next to the Appalachian Trail Conference sign

Source: Imgur

So, in the wake of his father’s death, it seems like Tarlin started to do some serious thinking about his life and his future. We’ll never know exactly what went through his mind during those days, but it’s clear that he spent some time reflecting on who he was and what kind of life he wanted to lead, eventually discovering a new passion that would come to dominate the rest of his days.

A Love of Hiking Develops

Erika remembers that after her brother went to college, he really started to get into hiking more and more. “At some point after college … he spent more time hiking, more than usual. I can’t say what pushed him to do that. He clearly loved it, and he obviously has the respect from the other hikers. That was his life.”

Baltimore Jack with five friends posing for a photograph mid-hike

Source: Flickr

As Erika admits, she wasn’t exactly sure what drew Tarlin to hiking, but it was clear that he had a real passion for it. Whenever he could, he’d head out and hit the trails: exploring nature, enjoying the fresh air and wonderful views, losing himself in the wilderness, and engaging with the natural world rather than cooping himself up indoors or in the city.

Life Goes On

While Tarlin’s passion for hiking was clear, he still remained committed to leading a pretty normal life when he wasn’t out on the trails. He graduated from Brookline High School in 1976 and then went to Hampshire College in his home state of Massachusetts, graduating in 1980 with a degree in history.

Baltimore Jack wearing a red vest, sunglasses, and a backpack getting ready for a hike

Source: Pinterest

It was just a few years after his graduation that Tarlin met a young woman named Allegra Brelsford, who was a student at Smith College, also in Massachusetts. The pair met while attending a party that had been organized for students and graduates to watch a film entitled The Day After. Right from the start, some kind of magnetic attraction seemed to draw the pair together.

An Instant Attraction

In an interview, Brelsford can still remember that first meeting with Tarlin. She says that his intelligence and charisma instantly attracted her. Calling him a “big presence in the room,” she adding that his “dashing” good looks also drew her in. She compared him to a figure from romantic poems of the past, adding that he had a wonderful sense of humor too.

Baltimore Jack standing in front of a grill

Source: Imgur

Tarlin and Brelsford began dating and were soon engaged. They got married in 1984, and, only one year later, they welcomed their baby girl Jillian into the world. For a while, it seemed like Tarlin was going to follow the typical “path” after all of getting his college education, finding a wife, and settling down to start a family, but things took a dramatic turn from that point.

A Dramatic Change

Sadly, as time went by, Brelsford began to realize that the man she had so quickly fallen in love with and married just wasn’t cut out for the typical family life. And as time went by and the family began to encounter some financial difficulties, she began to wonder how long they’d really be able to keep their marriage going.

Baltimore Jack standing in the middle of a store with shirts and sunglasses on the wall behind him

Source: Pinterest

Eventually, Brelsford and Jillian moved in with her mom and dad, and Tarlin simply disappeared from their lives. Many people might feel a lot of bitterness or resentment, but Brelsford accepts that Tarlin wasn’t the right fit for her. He just wasn’t the sort of guy who “couldn’t be pinned down,” she said. She married again a few years after he vanished.

Trying to Find His Way

There are many stories, myths, and unconfirmed reports about what happened to Tarlin next. Some stories suggest he spent time working at a video store in Boston, while others say he wandered around, taking on various odd jobs and trying to find out what he really wanted to do with his life from that point on.

Baltimore Jack standing near a tent wearing his backpack and hat, ready for a hike

Source: Twitter

It was clear that the usual path just wasn’t for Tarlin. He’d tried the marriage and kids route, but it hadn’t worked out. The one thing in his life that really meant more to him than anything else was hiking, and so, in 1995, after a decade of trying to find himself, he began his first hike along the Appalachian Trail.

An Iconic Trail

In the world of hiking, the Appalachian Trail is widely regarded as the greatest and most iconic trail of them all. Work first started on the trail back in the 1920s, and it wasn’t completed until 1937. It changes a little with every passing year, and over 30 trail clubs work to maintain it too, with the whole thing passing through a grand total of 14 states.

A sign leading to the Appalachian Trail

Photo by imageBROKER / Shutterstock

Countless people have taken on the trail over the years, but the vast majority of them only hike a relatively small section of it. The whole thing is over 2,000 miles long. It can take an exceptionally long time and requires incredible levels of physical fitness to complete in a single season. Only several hundred people succeed each year. They are known as thru-hikers.


The term ‘thru-hiking’ or ‘through-hiking’ is used to describe the process of hiking continuously from one end of an established hiking trail to the other. The term is closely linked with the Appalachian Trail, and the idea of thru-hiking the AT is something that many hardcore hiking enthusiasts hope to accomplish someday.

Emma “Grandma” Gatewood with the Appalachian Trail sign behind her / Emma “Grandma” Gatewood standing with her cane and a bag of personal items

Source: Imgur / Pinterest

It’s almost seen as the holy grail of hiking in the United States, and to successfully complete an official thru-hike of the AT, the whole thing needs to be done within 12 months. There have been some very famous Appalachian Trail thru-hikers over the years, such as Emma “Grandma” Gatewood, who completed her first thru-hike at the age of 67 using only simple gear like sneakers and a blanket, rather than sturdy hiking boots and a comfortable sleeping bag.

Taking on the Challenge

As a lover of hiking with a real passion for adventure, it seemed fitting that Tarlin would try his skills out on the Appalachian Trail. By the mid-1990s, he was living in the town of Hanover, New Hampshire, which was situated at mile 1,748 of the AT, so it is believed that Tarlin met several hikers on their way along the trail and learned more about it in the process.

Baltimore Jack with other hikers posing behind a red Jeep

Source: Facebook

He also remembered a promise his own father had made to him when he was younger, that they would hike the AT together someday. Sadly, Tarlin’s dad never got to live out that dream, but Tarlin was able to give it a try alone. In April of ’95, he hitchhiked along I-95 to Georgia and the AT’s southern end.

The Start of Something Special

This was the beginning of Tarlin’s first real foray onto the Appalachian Trail, even though he had walked sections of it before, and it was also the beginning of a whole new life for him. He’d saved up some money from working in a convenience store back in Hanover as well as from chopping wood on a large estate in exchange for rent-free living in a cozy cabin.

Baltimore Jack with random campers

Source: Facebook

Now, finally, he was ready to make his mark on the AT. With a set of dog tags from his father wrapped around his neck and a huge 60 lb backpack on his back, that he would later become famous for, he set off. It was at this time, as well, that his new nickname of Baltimore Jack began to develop.

A Nickname from the Boss

The name “Baltimore Jack” came from a Bruce “The Boss” Springsteen song entitled Hungry Heat. The first lines of the song are, “Got a wife and kids in Baltimore, Jack. I went out for a ride, and I never went back. Like a river that doesn’t know where it’s flowing, I took a wrong turn and I just kept going.”

Baltimore Jack posing with a woman

Source: Instagram

Many people believed that the name was chosen because of how it reflected Tarlin’s own life. Still, he always argued that he hadn’t walked out on his wife and daughter. He believed his wife had done the right thing and walked out on him after seeing that he wasn’t a good match for her.

A Failed First Attempt

Even though Baltimore Jack would go on to become a veritable legend of the Appalachian Trail and complete the whole thing a bunch of times, his first attempt at thru-hiking the whole thing didn’t end quite the way he had hoped when he first started out.

Baltimore Jack standing in a kiosk with snacks around him

Source: Facebook

Jack nearly made it to the end of the trail, having successfully hiked hundreds of miles. Unfortunately, not far from the end, in a section of the trail known as the Hundred Mile Wilderness in Maine, which leads towards Mount Katahdin, Jack fell and got injured. He had to limp his way back home to Hanover. After healing, he spent the subsequent winter working hard to save up cash for his next attempt.

The Legend Begins to Grow

In the years that followed, Jack went on to complete the Appalachian Trail on more than one occasion, becoming something of a local legend for trail enthusiasts as well as first-timers. Rumors started to spread about this mysterious man who always carried a heavy backpack and was often spotted with bandages all over his knees.

Baltimore Jack sitting and looking at photographs with a young girl

Source: Flickr

Another aspect of Jack that became legendary was his dedication to the act of hiking. He was a pure hiker, through and through, and was often seen with bruises and cuts all over his body because he was so determined to follow the white blazes and walk the trail as he believed it should be walked, rather than using any shortcuts or skipping any sections to make it a little easier. He became synonymous with the AT itself.

Meeting Someone Special

In the fall of 1996, Jack was 38 years old, and his reputation as an Appalachian Trail legend had been firmly established. So, when an 18-year-old young woman named Jen Whitcomb was looking to learn a bit about the trail and give it a try for herself, she decided to try and get in touch with Jack.

Baltimore Jack posing with a woman he helped out hiking and her baby

Source: Facebook

“Everybody said he knew everything about the trail,” explained Whitcomb in an interview, later on, adding that she tracked Jack down in a coffee shop and simply said she wanted to go hiking. Immediately offering her a seat, Jack said he could help and so began a wonderful friendship between the two.

A Unique Bond

Jack and Whitcomb became the best of friends. They planned separate hikes along the AT in 1997 and actually crossed paths in North Carolina after Whitcomb sprained her foot, and Jack caught up with her. She remembers how he was such a good storyteller and had such intricate knowledge of the trail, making him one of the trail’s true experts.

Baltimore Jack in orange clothing standing inside of a hiking store

Source: Twitter

Later on, when Whitcomb went back to college, she offered Jack a place to stay in her dorm. He looked out for her and helped out other kids with their history papers and showed a lot of kindness and care to the people he met each day. Some thought that he treated Whitcomb like an adopted daughter, but he also always used to tell her about his biological child, Jillian, adding that she “has a better father now” and that he wasn’t fit to raise her.

Back to the Trail

In the end, Whitcomb graduated from Dartmouth and joined the Coast Guard, moving out west to start a new life and begin her own family. Her friendship with Jack came to a close, and the legendary hiker simply got back out on the trail once again. This was around the turn of the millennium, at a point where Jack’s persona had been fully established.

Baltimore Jack petting a cat that is sitting on a wooden picnic table

Source: Facebook

In the years that followed, Jack continued to be one of the most dominant characters in the history of the Appalachian Trail. Almost everyone who hiked the trail had at least heard of him, and many of them crossed paths with him too. Some didn’t exactly see eye-to-eye with Jack because of his big personality and unique character, but many folks loved his charm, wit, and friendliness.

An Internet Authority

When he wasn’t on the trail or chatting with people at hostels, coffee shops, and other locations around the trail, Jack spent plenty of time on the internet, sharing his views, stories, and advice regarding the trail with others online. He wrote countless messages on various websites, mostly about hiking and the trail.

Baltimore Jack drinking milk

Source: Imgur

He wrote thousands of posts on the popular White Blaze forums, for example, as well as writing his own guides and recommendations for those who were new to the trail or thinking of hiking it for the first time. Just like in real life, Jack became famous online for his extensive knowledge of the AT, as well as his outspoken views on how it should be approached.

Keeping the AT Accessible

A big part of Jack’s philosophy towards the Appalachian Trail was that it shouldn’t be seen as some scary, daunting challenge that only the most athletic and prepared people could accomplish. He didn’t like the concept of people being too intimidated to give it a try, so he always tried, in his online posts and in real life, to make it as accessible and enjoyable as possible.

Baltimore Jack leaning against a wall in his hiking boots

Source: Flickr

He had a “keep it fun” attitude to the trail and even wrote his own “Resupply Guide” for first-timers, introducing them to the best taverns, guesthouses, and stopping points along the trail to make the most of their journeys. In one post, he famously stated that there was no “right way to hike the AT,” adding that everyone could approach it in their own way and get their own experiences and benefits out of it.

End of the Road

Unfortunately, despite his love of hiking and his passion for the AT, Jack couldn’t keep it up forever. He was a very fit young man in his early years who was able to walk 20 miles a day, even with the huge backpack on his back, but, by the time 2003 came along, and he’d completed his eighth thru-hike, his body started to struggle.

Baltimore Jack hanging onto rocks on a small waterfall

Source: Imgur

He had had a lot of issues with his knees throughout his hiking career, and many people often spoke of the dirty bandages they saw him wearing around his legs regularly. Well, Jack’s knees eventually gave out, and he knew that his days of thru-hiking were probably over at that point. But his relationship with the trail wasn’t finished yet.

Trail Angel

A “trail angel” is basically someone who doesn’t actually hike themselves but supports the trail and its hikers in other ways, perhaps through donations or voluntary services. That’s pretty much what Jack became once his knees gave way. He still wanted to spend time on the trail, even if he couldn’t go the full distance anymore, so he started spending his time as a kind of angel.

Baltimore Jack standing in front of a grill with a plate of food

Source: Instagram

In the years that followed, Jack would hang out at hostels and stopping points along the trail, cooking for hikers who were passing by, sharing stories, offering advice, and basically being a Good Samaritan to so many people just like him who had chosen to make that incredible journey for themselves. This dedication only helped his cult status grow even further, with people flocking from far and wide to meet Jack, hear his tales, ask for his advice, or bring him gifts of cakes and whiskey.

The Last Days of a Legend

All good things must come to an end, and all lives, no matter how extraordinary, eventually terminate too. The man we knew as Baltimore Jack, the legend of the Appalachian Trail, sadly passed away in May of 2016. He was 57 at the time. The cause of death was listed as heart complications.

Baltimore Jack standing around with fellow hikers

Source: Flickr

Even though Baltimore Jack was a seasoned hiker, he was still a big drinker and a heavy partier. He wasn’t in the best physical shape, according to those who knew him best, which may have led to his relatively early passing. Still, he managed to fit an awful lot of adventure into his life, touching people from all across America and beyond through his many journeys and leaving behind an unparalleled legacy too.

Outpourings From Far and Wide

As soon as the news of Baltimore Jack’s passing began to spread throughout hiking circles and communities, an absolute outpouring of condolences, messages, and stories began to be posted online, on social media sites like Facebook as well as on Appalachian Trail message boards and hiking forums, with countless users loading up their computers and typing out their own personal messages.

Baltimore Jack sitting at a picnic table with his arms crossed

Source: Imgur

So many people had been touched by Jack at some point in their lives, and many of them wanted to share their stories to honor his memory and bid him a fond farewell. Of course, not everyone who met Jack in real life developed a fondness for him, but in the wake of his passing, there were nothing but positive, inspiring stories about him all over the internet.

Endless Stories

On the internet, one can find countless stories, homages, and happy memories associated with Baltimore Jack. A man named David Ryan recalls how Jack actually saved his wife after she broke her leg while hiking the AT, carrying her over his shoulder from the trail to the road for rescue. Others, like Anna Ball, who thru-hiked the trail in 2014, remember Jack cooking some delicious suppers and dinners to lift their spirits and energize them for the days ahead.

Baltimore Jack joking around with Joel Urbine “Tricks.”

Source: Instagram

Many more have written about how approachable and friendly Jack was, how he was always willing to chat with new people, answer questions about the trail, share stories, and provide advice to newbies. There are many more stories of him handing out AT patches, soaps, supplies, whiskey, and other random gifts to people he met, both in Hanover and out on the trail itself.

A Hostel in His Honor

Baltimore Jack left behind an unmatched legacy, and people will continue to tell tales of his amazing adventures and unique personality for years to come. The AT won’t quite be the same without him, but his memory lives on in a variety of ways. In the last two months of his life, Jack lived in Franklin, NC, volunteering at a local hostel.

Jack with another man outside of the Hostel

Source: appalachiantrail.com

There, he chatted with fellow hikers, offering advice and sharing the benefits of his experience and wisdom. After he died, the hostel was actually renamed “Baltimore Jack’s Place” in his honor. Visitors to the hostel will be able to learn about Baltimore Jack and pay their respects to this very special man.

A Legacy Like No Other

Whether they knew him as Leonard Adam Tarkin or as Baltimore Jack, it seems that countless people were touched and inspired by this truly special man. He was a little different from everyone else. He saw the world in a different light and wanting to lead a special kind of life, and that’s exactly what he ended up doing.

Baltimore Jack dressed up in funny clothing posing near a railroad track

Source: Flickr

The AT has seen some real heroes and amazing characters over the years, but nobody has marked that trail quite like Baltimore Jack. Thru-hiking the trail eight times in total, he set the standard for hikers everywhere, while still maintaining an accessible, friendly, affable personality that endeared him to countless lives. He’ll be remembered fondly and always has a place in the history of the Appalachian Trail.