If you’ve ever considered a career in trucking — or you’re already behind the wheel but looking for more flexibility — seasonal truck driving jobs might be the perfect fit.
Whether you’re aiming to boost your income, explore a seasonal position before committing full time, or take advantage of hiring surges during busy months, seasonal roles offer both opportunity and variety. Companies across the country, including Service One Transportation, regularly hire seasonal drivers to handle increased freight demand — especially during the holidays, harvests, and retail booms.
Let’s break down what you can expect from these temporary jobs, what qualifications are needed, and why this route could lead to something more long-term in the trucking industry.
What Are Seasonal Truck Driving Jobs?
Seasonal driving jobs are temporary positions that help companies keep up with peak demands throughout the year. These roles are particularly common in:
- Holiday seasons (think UPS, FedEx, and retail delivery spikes)
- Harvest periods in agriculture-heavy regions like Central California
- End-of-quarter or end-of-year logistics pushes for retail and e-commerce
- Construction or road maintenance periods that pick up during spring and summer
A seasonal position might last a few weeks to a few months, depending on the location, company, and freight volume. While these jobs don’t always guarantee long-term employment, many companies — including ours — use seasonal hiring as a way to find new professionals who may later join the team full time.
Who Should Consider Seasonal Driving?
These jobs are ideal for:
- Retired or semi-retired truck drivers wanting to stay active without full commitment
- New drivers completing CDL training and looking to gain experience
- Workers in industries with off-season downtime (like construction or farming)
- People looking to earn extra income during holidays or specific parts of the year
- Anyone testing the waters before joining the industry permanently
It’s also a great way to explore different shifts, types of freight, and company cultures — without feeling locked in.
What Kind of Work Can You Expect?
Seasonal drivers may be asked to:
- Operate trucks across regional or local routes
- Pick up or deliver goods to meet high customer demand
- Work during night hours or weekend shifts
- Load and assist with unloading depending on the cargo
- Coordinate with dispatchers, warehouse staff, and colleagues
Depending on the business needs and the season, the pace can be fast — but many drivers enjoy the challenge and the chance to try new routes or freight types.
Seasonal Positions with Service One Transportation
At Service One Transportation, we understand that not everyone is looking for a long-term position right away. That’s why we regularly offer seasonal truck driving jobs to help with demand spikes — while also giving drivers a chance to get to know our company, team, and operations.
Whether you’re based in Wisconsin or looking to drive through the Midwest, our seasonal roles come with competitive pay and the support of an experienced, driver-focused team.
And if you like what you see? Many seasonal drivers who perform well are invited to stay on in full time roles.
Benefits of Going Seasonal
Choosing a seasonal route has its perks:
Flexibility
You can work for a week, a few months, or even come back every season as needed.
Experience
Great for new drivers looking to gain road time and learn company systems.
Path to Full-Time
Seasonal work is a common stepping stone toward permanent employment. Companies often review seasonal performance when hiring for long-term positions.
Added Income
Extra cash during the holidays or downtime from another job — without long-term commitment.
Human Connection
Despite being temporary, these roles allow you to build relationships with colleagues, dispatchers, and customers — all essential for growing your network in trucking.
What You’ll Need to Get Started
Most companies require the following, even for seasonal roles:
- Valid commercial driver’s license (CDL)
- Ability to operate commercial vehicles safely
- Clean driving record and adherence to state laws
- Completion of any required verification or background checks
- Willingness to follow federal and company safety protocols
At Service One, you’ll also go through a quick but thorough onboarding process. Once your verification is complete and your connection to dispatch is set up, you’ll be ready to hit the road.
We make it simple to get started — no “ray ID” tech confusion or red tape. If your verification successful waiting status is approved, you’re clear to roll.
Health & Safety First
Even seasonal drivers deserve top-tier treatment. At Service One, eligible seasonal and full time drivers can benefit from:
- Health insurance
- Dental insurance
- Retirement benefits (for extended or returning seasonal drivers)
- Regular vehicle inspections and maintenance
- Ongoing training and safety support
We’re committed to treating every driver — whether temporary or long-term — like part of the family.
Ready to Hit the Road?
If you’re interested in flexible work, new challenges, or just want to try something different this season, seasonal trucking might be exactly what you need.
At Service One Transportation, we’re always looking for skilled and motivated individuals to assist with our busiest times of year. Whether you’re a veteran truck driver or fresh from truck driving school, we’ll help you verify your qualifications and get started.
And who knows? What starts as a temporary role might lead to a lifelong career behind the wheel.
👉 Explore current openings and apply today at Service One’s Seasonal & Part-Time Driver Jobs page.