10 great reasons to get a summer job in Skagway!

with 13 Comments

img_3057-e1437259336634Last Spring, Gabby and I decided to pack our things (once again) and head off to yet another employment adventure. This time we decided to move to Skagway, Alaska for a sumer job that would last for only 5 months. After checking out Coolworks.com, and filling out a few applications, we were both hired by a Brewery/Restaurant in the busy cruise ship port-of-call town. We had almost no idea what to expect. Here’s what we learned!

1. Skagway, Alaska is summer camp for adults.

We were shocked to realize that nearly everyone in town was our age, everyone was from everywhere, and there were no boring people in sight. We fell in love instantly. According to the most recent census the population of Skagway is about 900, but in the summertime there are over 2,000 seasonal workers who flock here for summer jobs. There’s tons of work in Skagway, all you have to do is apply. You can work for restaurants, bars, tour operators, the train, the hotel, the bus companies, or any of the various retail locations in town. Skagway is set up just the way it was when it was built in 1898. Broadway is lined with restored period era buildings, complete with false fronts, and there are wooden boardwalks along the main streets. It’s a town rich with history, which it celebrates and holds close.


Skagway has 5 bars in town, each with their own unique attributes; one of them even stays open until 5am, and reopens for breakfast at 8. Also, Marijuana is legal and (Updated: 3/2017) available at the local dispensary! There’s live music to hear on almost any given night all summer long from local bands and open mic, to Karaoke for the brave.


2. Get hired and move in!

When we arrived, we quickly learned that the most difficult thing about getting to Skagway was finding a place to live once you got there. The entire town is only 4 blocks wide by 22 blocks long; and it’s fully enclosed by mountains and ocean. There just aren’t enough houses for all of the people. Therefore, most summer jobs offer housing. The easiest way to get housing in Skagway is to get hired for the summer sometime around February or March and move in around April/May; that way they don’t run out of space before you get hired.


3 . End Dates

Every seasonal contract comes with something very important written on it, your end date. Having a summer job with an end date allows you the freedom of knowing exactly when you’re going to be done working. You can make plans to travel to your next destination, or back home, or to your next job easily. It also prevents you from getting burnt out since you can clearly see your end date in sight.


4. Community

The community in Skagway is unlike any I’ve ever seen anywhere. Most people here are only here for the summer, although many who come here once end up coming back year-after-year. Very few live here year-round, yet there are more and more young people deciding to stay for the winter each year. People take care of each other and form close relationships, yet still respect each other’s privacy. You can be whoever you want to be here, there’s little judgment, and there’s a friend for everyone. Besides, we’re all a bunch of weirdos anyway.


5. Tourist Money

Even if you don’t particularly enjoy having your town overrun with tourists each day, they bring something very important off the ships and into town with them, money, And you’re going to get that money. The tourists keep this town alive, and when it comes down to it, they’re the reason we come here. Their money goes into our paychecks, and they’ve got a lot to spend. We wouldn’t come here if it wasn’t worth our time and money to get here every year. Servers, bartenders, bus drivers, and tour guides also stand to rake in lots of tips in addition to their hourly wage. (As a side note, servers and bartenders must also be paid no less than the AK state minimum wage) In short, the money is good.


6. No need for a car.

Our choice of vehicle for the summer in Skagway We love tandem bikes!
Our choice of vehicle for the summer in Skagway We love tandem bikes!

When the entire town is 22 blocks long by 4 blocks wide, there’s rarely any need for a car. That’s not to say that people don’t bring their cars here, it’s always nice to drive somewhere across town and get there within 3 minutes, but you can easily get by with a bike. Some of those people with cars are willing to let you borrow theirs if you needed it, and if they’re asked politely. We leave ours safely down south for the whole summer.

7. Hiking/ Outdoor Activities

Skagway is heaven for anyone who loves the outdoors. There are seemingly endless hiking trails including the 33-mile Chilkoot trail used by thousands of prospectors during the Klondike gold rush. Apart from hiking there’s also camping, backpacking, mountain biking, kayaking, fishing, rock climbing, cliff jumping, and an 18-hole disc-golf course. Not to mention, you’re only 13 miles from the Yukon. If you’re not an outdoorsy type, you might just be before Fall.

Canoe on Lake Bennet in the Yukon Territory
Canoe on Lake Bennet in the Yukon Territory


8. Tours and Excursions

Skagway is a cruise ship port-of-call, so there’s a lot of tours and excursions here for those cruisers. The fun thing is, that as a local, you can do them too! There’s river rafting, dog sled tours, gold panning, zip lining, horseback riding, fishing tours, a brothel tour, and so many more. And since the new legislation, there’s even a marijuana grow tour! If you happen to work for one of these tour operators, you might even get to do a lot of these for free.

Gabby and I, and our friend Chris on a helicopter tour to Mead Glacier on my birthday in 2014
Gabby and I, and our friend Chris on a helicopter tour to Mead Glacier on my birthday in 2014

9. Long Days

By the summer solstice, the sun sets in Skagway, AK around 10:30PM and rises around 3AM. The sky never even fully darkens in-between. These long days allow you to fit so much more into your daily schedule. Sure, it takes a little getting used to. It’s a little weird at first to wake up to the sun at 4:30AM and to go to bed when it’s still light outside. But soon you’ll see how much you benefit from having 6 extra hours of light each day. When it gets dark around 8:00, your brain tells you it’s time to go home. Here in Skagway, it stays light until much later so it’s always easy to stay out and do things.


10. Friends for life

You’re going to make a lot of friends in Skagway. You’re going to work, live, and play with a lot of the same people day in and day out. You’re going to develop strong bonds with people that you can’t even explain to your friends “down south.” Then, when September comes, you wipe your tears, say goodbye, and send them off. Then, maybe you get to see them next summer, or maybe you make plans to meet them somewhere else in the world. Either way, you’re going to make new friends for life here, you can’t even avoid it.


Take the leap! Sign up below to receive our free Seasonal Work Handbook! We’ll give you the tools to break free of your daily grind!

Some of our friends out at Long Bay
Some of our friends out at Long Bay



What’s stopping you? Have you ever worked a seasonal job? What were your experiences like?

13 Responses

  1. Jesse Zayas
    | Reply

    Great read! Thanks for writing about your experiences and sharing.

    • admin
      | Reply

      Thanks, Jesse! We LOVE Skagway and we wish everyone knew just how awesome this place really is.

  2. backpaco
    | Reply

    Great blog!

    Lucky you always wanted to have a slice of life in Skagway I loved my few hours there!

    • admin
      | Reply

      Thanks, Paco!

      This place really is great, sorry to hear you had such a short amount of time to experience it. If you ever want to spend a summer working, doing whatever makes you happy, and making great friends, I can’t recommend Skagway enough.

  3. Small Town Washington
    | Reply

    I love Skagway. We stopped and camped there about 12 years ago. It was such a great time and one we talk about often. Would love to go back.

    • LocalNomads
      | Reply

      That’s awesome, it must be so different now. Do you remember where you camped? There are so many great places to hike and camp in Skagway.

  4. Lori
    | Reply

    This sounds so amazing! I am so jealous! 🙂

  5. Bethany
    | Reply

    Lovely place! lovely people! working here has been an incredibly fun adventrue

    • LocalNomads
      | Reply

      Did you work there again this summer? We have a few friends from the dredge that stayed the winter. That little town will always feel like a home I can go back to. I just love it up there.

  6. AlicevstheWorld
    | Reply

    This is an awesome post! I’ve never really considered summer jobs abroad but they sound like a very tempting option :).

  7. Jonathon Andrews
    | Reply

    I worked there the last four years during the summers.
    It’s a great place to earn a decent amount of money in a relatively short time. But there’s things to keep in mind:
    1. Living expenses and food are expensive.
    2. Produce comes into town once a week, but it’s not a lot. If you’re not at the store on Wednesday or Thursday, it’s very slim pickings.
    3. People move from company to company throughout the summer due to conflicts at work, or a general need for a different job. If you don’t like your job, there’s going to be somebody else who’s willing to hire you.
    4. Reputation is everything in this town, and of your character goes to shit, the town will know by 5pm the following day.

    • LocalNomads
      | Reply

      Thanks for your comments, Jonathan! It’s cool to hear from someone else who’s lived in the place we’ve come to love so much.

      We completely agree with your 4 points about Skagway. We never meant to imply that Skagway is a place without challenges.Living in Alaska is clearly not for everyone. We found the cost of living to be quite high in Skagway also, especially when you factor the quality of what you’re paying for.

      The produce situation was particularly challenging for us as well. We tried multiple different options including signing up for the “weekly mixed bag” from You Say Tomato, and have heard about some online grocery services similar to this as well. There doesn’t seem to be a great way of dealing with it other than good planning and hitting the store on Tuesday/Wednesday.

      It’s funny how things work out with jobs in Skagway. We’ve always had the mindset that living in Skagway isn’t about the job you’re working, but how you spend your time outside of work. The long days give an amazing opportunity to really squeeze a lot out of a summer if you work it right. We worked for 2 different companies while we were in Skagway, and most of the people we know up there have worked for multiple companies as well. Whether you switch at the beginning of the season or mid way, it seems like there’s always plenty of jobs to go around. 🙂

      We’ve also seen people get “run out of town” for lack of a better way of putting it. Sometimes people fuck up really bad in Alaska, and sometimes shitty people end up there too. However, we’ve found the Skagway community to be overwhelmingly welcoming and accessible. We’ve met some of the most amazing people there, and our friends who’ve lived in Skagway for much longer than us have had similar experiences with the local community.

      Living in Skagway has its pros and cons like anywhere else. Thanks for helping us to share some of the more challenging aspects of this interesting place. Great to hear from you!

  8. Annalicia
    | Reply

    I just met a local from Skagway on Thanksgiving day. She offered me a summer job and I have been researching everything Skagway for the past three days. Would really like to hear more from you on your adventure. Please feel free to contact me via email that was provided.

Leave a Reply