Skagway — A Borough In Alaska

On a mildly warm evening in early October, we were ordering craft beer, seated on a patio in Portland, Oregon.  The waiter asked for our I.D.s.  There were six of us.  After reading Florida, New York and Missouri licenses, he gave us a skeptical look.  No, they were not fake.  Five months earlier, we were strangers.  We were each on a journey back to our respective states from a magical place that had brought us together.  On this day, though, we were companions and best friends, each in love with wandering and spending time with free-spirited people, enjoying the final meal we would spend together.


From the earliest time that I can remember, I’ve been mesmerized by maps and the thought of exploring the world.  Road trips were my favorite kind of vacation as a kid.  I would stare out of the window and watch the scenery change, as if the roadside view were a film reel flashing before my eyes.

When I turned 25, I had what I refer to as a ‘quarter-life crisis’.  Some may call it an over-extended panic attack.  There was so much world out there that I had not yet explored.  I didn’t even have a passport.  My inability to stop time paired with student loan debt looming over my head had me frantically evaluating my life.  I was never going to travel like I had always dreamed.

After a few months of soul searching, instead of wallowing in my own self-pity, I decided to research some jobs far from my home.  I have lived in Georgia and Florida my entire life, so I started my Internet search with jobs in the Rocky Mountains.  Somehow, though, I happened upon a seasonal job opening in Skagway, Alaska.  Whatever possessed me to apply, be it destiny or chance, paid off in a big way.  When I boarded my flight in Atlanta, my nerves were on high alert.  I had waved goodbye to everything familiar and as the plane took off, my mind teeter-tottered from feelings of nervousness to those of unabashed excitement for the journey ahead of me.

Before leaving for Alaska, I learned as much as I could about Skagway from the Internet (which turned out to be very little).  Skagway was a very small, historical town at the end of the Lynn Canal in southeast Alaska.  In the late 19th Century, Skagway was a safe place to stay before setting out to look for gold in the Alaskan wilderness.  This was just about all I knew before deciding to live there for the next five months of my life.  I could not have predicted the lasting mark that Skagway would leave on my life and my heart when I set out on this adventure.

When you’re young, people warn you never to talk to strangers.  Some people even advised me of this prior to my solo trip across the country.  Strangers talked to me, though, and I distinctly remember the phrase, “Speak when you are spoken to,” from childhood, as well.  From the moment I hugged my mother goodbye at the airport, every encounter I had was with a stranger.  So, when I took the middle seat on the first flight, I met the first two strangers to be accompanying me for the next seven hours of my life.

I’m an anxious flyer, so they were probably trying to comfort the panic-stricken young lady clenching her novel beside them.  We were almost immediately engaged in conversation.  This flight was set to land late at night in Seattle, and the two gentlemen sharing the row with me were headed home.  Vincent, Matthew and I got to know each other over discussions of Atlanta and what they did for work there.

Just as they had entrusted me with their own plans, I felt obligated to share as well.  Both men became wide-eyed at the thought of my venture to a foreign place.  “It’s great that you’re doing it while you are young,” said the man to my left. Each of them explained how they had children, now, and would never have this chance.  I could see a look of longing on their faces for, what I assumed, was a youth they no longer felt within themselves.

Matthew was a businessman and his goals were framed by dollar signs.  He told me of his own young adulthood jaunt in Denali National Park for a summer and said, encouragingly, that it was like nothing he expected, but it was better.  My other new acquaintance, Vincent, told me his biggest dream was for his children to grow up happy and explained the sadness that comes along with leaving your family behind to travel for work.

When we landed in Seattle, Matthew said farewell and Vincent showed me to baggage claim.  He waited with me until my bag came gliding towards us and wished me luck on my travels.  That was the last I saw of either of my new travel buddies.  These were the first of many short-term friendships that I would make on the trip to Skagway.

On the connecting flight from Seattle to Juneau I sat next to a man who was also going to Skagway for the summer; for the fourteenth year in a row.  Dennis told me more about the little town than the Internet ever could and I appreciated the insider information.  When the plane descended below the clouds and I saw the mountains of Alaska for the first time, tears welled up in my eyes.  I was starting to understand the call of the mountains I had heard so much about.

I had an overnight layover in Juneau before my 12-passenger plane was set to take off for my final destination, so I told my new friend I would see him later as he boarded his own flight to Skagway.

At this point, I had talked to several people who had been to Alaska before and had admittedly fallen in love.  Each of their eyes illuminated with a sense of wonder when they spoke of the place.  One woman even approached me in the airport to let me know that she heard my story and had done the same 35 years earlier.  She loved it so much she made Alaska her home and never looked back. Even though I had stepped far outside of my comfort zone, with a few confident nudges from strangers, I was gaining trust in the direction my personal compass had led me.

Instead of staying in my hotel for the evening, I decided to venture downtown and explore.  Again, I was tense and nervous about being in a strange place all by myself.  It took a lot for me to even consider leaving the room.  My anxieties were calmed, though, once I was walking about the tourist shops and marveling at the unique local artwork.  When I sat down at a bar at the famous Red Dog Cafe, I was greeted kindly by a couple of Australian strangers seated next to me.

The couple was taking a long overdue honeymoon and inquired to whether I was on the cruise ship with them.  Once they knew my story, they, too, insisted that I would have the time of my life and praised me for exploring while I was still young.  During dinner, we taught one another of cultural differences and discussed higher education in each of our countries; they educated me on Tasmania and I told them about Florida.  At this point, my fear of strangers was dwindling and I realized that with each new encounter, I was not only learning about new people, but growing as an individual, too. It was easy to acknowledge that there was far more out there in the world than I had even imagined and my trip had barely begun.

The next day, I awoke before the sun was out and walked to the airport.  There was little to no security to go through and this struck me as odd, having left from one of the largest international airports in the world.  Then, I got to sit directly behind the pilot who, much to my amazement,  asked us which route we preferred; over the water or over the icefields. There were six or seven of us on the flight and the family of four that lived in Skagway immediately erupted with excitement to fly over the icefields.  Again, the nervous flyer in me was dreading a small craft flight, but this trip proved to be much more tolerable and had far better views than any commercial flight I had been on before.  I also learned more about the town I would be living in from the locals and met a fellow tour guide who would be spending the summer there for the first time, too.  He looked just as wary as I about the unknowns ahead of us and I was somehow comforted by our silently shared apprehension.

The lonely trip away from home turned out to rarely be lonely at all, and I was thankful for the strangers who quickly became friends and accompanied me along the way.


When I finally arrived in Skagway, my new boss picked me up from the airport (which was the size of a small apartment) and drove me around the four block wide and mile or so long town to point out the small grocery store, recreation center and cruise ship docks.  This was just before the open of the summer season in late April and many of the town’s shops had boards in the windows and people were cleaning up around the main street.  Broadway is only about seven blocks long, lined with colorful, vintage buildings and a wooden boardwalk.  Tourists escaping their cruise ships for a few hours flood this street nearly every day throughout the summertime.


Having lived in the South, I was enamored with the surrounding mountains jutting far above the small buildings.  I had been to the mountains of the midwest, but these were even more majestic.  They were still snow-capped and decorated with bald trees upon my arrival.  Within weeks, though, blankets of the greenest leaves covered their rocky faces and dandelions and wild flowers sprouted up from every patch of grass in town.  White yarrow, purple fireweed and yellow butter and eggs began to cover the earth, speckling the fields with color.  Rather than being the winter wonderland many of my friends and family envisioned (calling me to ask if I had fallen for an eskimo or whether or not I lived in an igloo), the weather most often felt like a spring day back home.


I learned more about myself during the five months I spent working and (mostly) playing in the little town than I had predicted upon deciding to break down the barriers that were keeping me close to home.  Hiking through the mountains made me realize how deeply I loved being outside amongst the trees.  I began to notice the smaller things; the mushrooms and pine cones and ripples across lakes.  I was becoming more and more in tune with nature and the pleasure I got from seeing it up close.  I spent very little time staring blankly at television or computer screens, because there was constantly someone to have a conversation with or something new to see.


Being in the mountains had me realizing characteristics about myself that would never have come to my attention had I just stayed where I felt comfortable.  I was not content when I left and everyday in Skagway, I was exploring a new piece of my personality because I no longer had the crutch of familiar faces expecting me to be who I had always been.  I had become like the fireweed; blooming in the summertime, stretching towards the sky.  The flower gets it’s name because it has a tendency to grow out of the ashy earth after a forest fire.  This resonated with me and somewhat defined the purpose for my journey.  I had been in a dark place before I had the courage to stretch my boundaries. The abundance of the flower in the town was a reminder that despite the past or my age, there are always opportunities to grow.


Skagway is a small town, but it is home to some of the biggest personalities I have ever met.  Many of the summer residents don’t stay over the winter time because cruise ships stop visiting during the colder months.  The people who come to work here, though, are a breed all their own.  Especially here, I was unashamed to introduce myself to a new face.  No one was a stranger because they were sharing with me the quirkiness of this place.  Skagway is a safe-haven for the extroverted and adventurous types.


Being here was like taking a giant step back in time.  There were “prostitutes” roaming the streets by day, hollering out of second story windows at tourists passing through the shops.  By night, those of us who had come to cash in on the modern-day gold rush would gather together at one of the three bars to relax after a hard day’s digging.  The boardwalk emptied after 9 p.m. and the only people walking around were those I recognized from working at the ship docks.

The three radio stations played NPR or a small number of locally produced shows, often asking if anyone had seen the earring that Cheryl had misplaced somewhere between 2nd and 5th Avenue on a night out.  The earring was probably hanging from the bulletin board at the entrance of the grocery store, accompanying lonely gloves separated from their partner and alongside an ad in search of a VHS rewinder.  The micro-community was a refreshing change from fast-paced city living.  I longed to find Cheryl’s earring, simply to solidify my small part in the neighborhood.

I became very disconnected from the society outside of what we came to know as our own little cruise ship docked in paradise.  It wasn’t the breezy, palm trees swaying in the wind, our toes in the sand, kind of paradise.  This town nestled at the furthest reach of the ocean in the southeast portion of Alaska was a secluded oasis of people and places I adored more and more with each passing day.

We were nomads, hippies and wanderers.  It was as if we were on a working vacation. Everything happened slowly because everyone had a tourist’s mindset.  By midseason, the town began to feel like a real-life episode of Cheers when the tourists returned to their cruise ships.  I found friendship in many of the tour guides and local shop workers and never went out without seeing a familiar face.  Be it the bar, the grocery store or the post office, somebody knew me by name.  Before I knew it, I was dreading the day in September when I would inevitably leave all of the beautiful spirits I had met here.

We were immersed in the very small piece of the world surrounding us.  The energy of Skagway was bustling during the day and calm, yet brilliantly fun by night.  We were entertained with music provided by local musicians, open-mic nights showcasing the talent of our friends and hilarious bar games like Egg Roulette (opponents facing down 5 boiled eggs and 1 uncooked, over and over, until the last man standing is awarded the championship belt).   Otherwise, we gathered around bonfires to chat away the evenings.  These were the kind of people who always wanted to have fun. This was my community.

The conversations went deep here, too.  We only had a short time to get to know one another since the end of the season loomed ahead.  Five months seemed an eternity before I embarked on this journey.  Once I started getting to know people, though, those few months felt stiflingly short.  So, instead of talking about day-to-day business, we often engaged in conversations about society, traveling, our pasts or our dreams.  We bonded over our likenesses.  What would have been a debate with many of my friends and family back home, was often supported by the new people in my life.  My distaste for routine and conformity was shared.

The tides change drastically and often in this part of the world and this ebb and flow symbolized something within me.  My heart was the moon and I was being drawn into this place, yet my yearning for travel kept me from ever wanting to settle.  My emotions were as dramatic as the ocean’s movements.

Skagway taught me that home was not necessarily as simple as being the place you grow up.  Home is a feeling deep within a person.  Home is when your heart latches itself to a place or person and refuses to let it go without a little aching.  It’s a place where your confidence soars and you can be relaxed in it’s familiarity.  It is a peacefulness within myself.  No matter the location, I am now capable of bringing myself home; of taking a deep breath and feeling secure in the fact that this path is my home.  My heart is a map of places that I have cherished, dotted by people who have taught and loved me throughout my life’s journey.  Those dots increased tenfold after experiencing this seasonal lifestyle for a short time.  The internal map that, surprisingly, directed me towards Skagway is etched in the veins that send life to my heart.

Venturing out on my own was a decision that I wasn’t entirely sure was the right step to take when I started.  After living for just a short time away from everything I had known in my very small portion of the world however, I soon realized I had chosen this long, long ago.  I had been mesmerized by the yellow painted lines melting into the windshield as I drove down roads; hypnotized by mobility.  This was no small decision to get away.  This was a culmination of all of the urges I ever had to just go; of thoughts like, “What if I just kept driving?”  Succumbing to this urge to explore was the most awakening, exhilarating leap of faith I could have taken.

I am lucky enough, now, to have true friends spread out across the United States and even a few exploring other countries.  I acquired a passport over the summer and am anticipating many a stamp on the pages.  Taking this adventure was like dipping a toe into the water to test the temperature and without hesitation, I had the compulsion to turn and cannonball into the deep end.  I have been humbled, inspired, excited and ultimately, drowned in wanderlust.