Work and Travel: Winter Work at a Ski Resort

Have the itch to go travel, but need to make money along the way? I spent the last four months working at Stratton Mountain Resort in Southern Vermont, hit the ski slopes in my off time, and even managed to save up for the next adventure. Here’s some insight to my experience working a winter at a ski resort.

Job: Waitress

Location: Stratton Mountain Resort, Vermont


Winter at Stratton

Getting the Job

There are a few hundred ski resorts in the USA and somehow we managed to find ourselves in South Vermont. While working in Denali in 2013, Sean worked for an enthusiastic chef who went to work at Stratton the following winter. Basically, the job offer was on the table for work in Vermont when he was available. This year, it all just happened to work out. When we hiked Stratton on the Appalachian Trail, we went down the mountain and confirmed our jobs for the winter. In early August, we committed to the winter season beginning December 1st.

Sean and I both have extensive experience in the restaurant industry, and with a helpful reference on our side, securing our jobs proved simple. There are lots and lots of different types of jobs available at ski resorts including food and beverage, maintenance, retail, office work, massage, ski school, and much more.

stratton summer 3
Summer at Stratton


Both Sean and I averaged 40 hour weeks with possibility for overtime (holiday weeks were especially busy). We both typically had two (midweek) days off per week but occasionally worked 6 or 7 day weeks.


Sean and his bartending mentor, Rit.

On our days off, we would visit nearby Manchester Center (the closest small town about a 25 minute drive away), relax with craft beer, or, of course, try to improve our skiing skills. Perks of working at a ski resort? Free lifts, $10/ day or $5/ half day rentals, and a free group lesson. I had skied 4 or 5 times as a kid, but there were no mountains involved. We were brand new to the sport and very excited to embrace a winter hobby. We only got out on the mountain about 4 times due to lack of snow in New England this year. However, we enjoyed our time and are looking forward to (potentially) returning.



What can I say, resort work has its perk$. As a career server, I was very, very pleased with my finances this winter. I felt beyond blessed to have gotten a job serving at the always high volume restaurant, Grizzly’s, “The bar at the base, baby.” We opened at 11 a.m. to the pounding of ski boots tramping up the stairs for bar food and beers. The next 8 hours were incredibly fast paced, somewhat hectic, and always packed with people soaking up every bit of their vacation. I’ll have server nightmares about my Saturday shifts for awhile, but of course, they were worth every penny.


I worked with a team of all star servers who quickly became my friends. All ready missing you all!


Stratton Mtn has a small amount of employee housing, and since we secured our winter jobs so early, we were able to snag a room in Lift Line Lodge. Lift Line, a hotel built and probably also most recently updated in the 80s, was our home from December – March. I did my best to avoid the overly shared and rarely cleaned kitchen, ignore the sounds from other rooms through paper thin walls, and patiently wait on the one washer and dryer so many people needed to use. The good things? We lived on the mountain and never had to drive to and from work (especially helpful when it’s snowing). But a little research has shown that for $125 / week each we could have likely found an apartment or small house off the mountain. But then we might need 2 cars to accommodate different schedules…

So, yes Stratton (and many other resorts) has employee housing. The number of rooms does not meet the demand and many people find independent, seasonal housing near the mountain. The cost vs benefit analysis still hangs in the balance for me, but employee housing sure was convenient.


Never got tired of my view from work.


If you have been considering jumping into the nomadic lifestyle via seasonal work, I highly recommend making the dive! There are various locations and positions available seasonally that can allow you to see more of the world and still be making money. Why not spend your summer in Alaska and your winter in Hawaii? Check out for a preliminary search of what’s out there. This website connected Sean to his job in Denali which led to a job offer in Vermont. Which actually led to a job offer catering Coachella in Southern California. A quick search of “resort” + “insert cool place you want to go” + “employment” is a great way to get an idea of what jobs they need to fill, if they have (or can help you secure) housing, when hiring is, etc.

Who knows? You might even get to work at a place that celebrates Unicorn Tuesday too!!

6 Comments on “Work and Travel: Winter Work at a Ski Resort

  1. Pingback: Working in a Winter Wonderland | Infinite Geography

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  4. Pingback: A Unique Pre-Trail Experience in Coachella Valley – Infinite Geography

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