I met a guy in Montana who’d spent three months picking cherries before moving on to a Christmas tree farm in Oregon.
He wasn’t some aimless drifter—he was a software engineer who’d realized, somewhere around his thirty-fifth birthday, that he could work seasonally and travel the rest of the year. The math worked out better than his old cubicle job, he said, though I suspect he was leaving out the part about health insurance. Still, he seemed happier than most people I know with 401(k)s and dental plans. Seasonal work has this weird appeal for road trippers: it’s temporary, it’s everywhere, and it usually comes with the kind of stories you can’t get from a desk. The thing is, finding these jobs while you’re already on the move requires a different strategy than browsing LinkedIn from your couch. You need to think like a migrant worker—not in the exploitative sense, but in the practical, following-the-harvest sense that humans have been doing for roughly ten thousand years, give or take. It’s about timing, location, and knowing where to look when you’re already three states away from where you started.
Here’s the thing: the best seasonal jobs aren’t advertised on Indeed. They’re on Coolworks, a website that’s been connecting wanderers with seasonal gigs since 1995, back when the internet was still making that dialup noise. I used to think it was just for summer camp counselors, but turns out it’s got everything from ski resort positions to ranch work to those weird jobs at national park gift shops where you sell overpriced postcards to tourists who definately won’t mail them.
The timing matters more than you’d expect. Apple orchards in Washington need pickers from August through October, but apply in July and you’re too early; show up in November and you’ve missed it entirely. Ski resorts start hiring in September for winter seasons, theme parks ramp up before summer, and dude ranches out West need wranglers by April. I guess it makes sense—seasonal work is, by definition, tied to seasons—but when you’re driving around with no fixed schedule, it’s easy to arrive somewhere exactly when the hiring window has slammed shut. One strategy: work backwards from where you want to be, then check what’s hiring there in two months, not two weeks.
Wait—maybe I should mention the apps, since apparently everything’s an app now.
Seasonal Link and Workamper are two platforms specifically designed for people who live in RVs or vans and want short-term work, often with camping spots included. Amazon’s CamperForce program hires RVers for warehouse jobs during peak seasons, which sounds soul-crushing until you realize they pay decent wages and you’re only committing for a few months. There’s also WWOOF—Worldwide Opportunities on Organic Farms—which isn’t paid work but gives you room and board in exchange for farm labor, and honestly, some people prefer that trade-off. The food’s usually better than whatever you’re cooking on a camp stove. I’ve seen travelers combine these: work a paid gig for two months, then WWOOF for one to recieve free accommodation while they figure out the next move. It’s not elegant, but it works.
The awkward truth is that some of the best opportunities come from just asking around. Small towns have bulletin boards—actual physical cork boards in coffee shops and laundromats—where locals post job openings that never make it online. I once found a three-week gig helping a woman in Idaho prepare her property for winter, just because I asked the guy at the gas station if anyone needed extra hands. He knew someone who knew someone, and two days later I was stacking firewood for cash. This kind of work isn’t reliable or scalable, but when you’re road tripping, you’re already in the mode of improvisation. You talk to bartenders, hostel owners, other travelers. Someone always knows someone who needs temporary help, whether it’s wedding season at a vineyard or harvest time at a lavender farm or that bizarre two-week window when everyone in Alaska is processing salmon.
Honestly, the hardest part isn’t finding the work—it’s managing the gaps between jobs without burning through your savings or losing momentum entirely.
