Transtar Insurance Brokers
August 1, 2025

2025 Driver Appreciation Week: What Your Drivers Really Want

National Truck Driver Appreciation Week is coming up fast, September 14–20, 2025, and if you're thinking of tossing drivers a pizza party and calling it a day, it’s time to shift gears.

America’s truck drivers do more than just “deliver loads.” They keep the economy alive, navigate everything from brutal weather to roadside inspections, and somehow still make that 6 AM delivery look easy. The least we can do is show real appreciation for everything they do.

Here’s the thing: drivers don’t need another generic water bottle or flimsy tote bag. They need support that matters. So let’s dig into what drivers actually want this year and how your fleet can stand out for all the right reasons.

1. Better Schedules = Happier Drivers

If you want to show appreciation, start with the logbook. Long hours, inconsistent routes, and surprise dispatch changes wear drivers down fast. What they really want? A schedule that respects their time and lets them sleep in their own bed once in a while.

Pro Tip: Survey your drivers about their preferred routes and rest times. Use that feedback to tweak schedules, even if it’s just for Driver Appreciation Week. Little changes = big morale boost.

2. High-Quality Gear (That They’ll Actually Use)

Drivers don’t want another foam cooler or flimsy flashlight. If you’re gifting gear, make it quality gear.

  • High-end polarized sunglasses
  • Ergonomic seat cushions
  • Heated or cooling lunchboxes
  • Durable bluetooth headsets
  • Branded outerwear they’ll actually wear (think Carhartt, not clearance bin)

Pro Tip: Let drivers choose their gift from a short list. Empowering them with options makes the gift feel more personal and less corporate.

3. Real Recognition, Not Just Posters

Don’t just slap a “Thank You Drivers!” sign in the breakroom. Give real, individual recognition.

  • Spotlight a “Driver of the Week” with a cash bonus
  • Post short video shout-outs from dispatch, customers, or family
  • Send a handwritten note from leadership
  • Feature drivers in your newsletter or social media
  • Offer small bonuses or extra PTO to top performers

Pro Tip: Ask your customers to send a message or testimonial for their regular drivers. That third-party validation hits differently.

4. Invest in Their Future

Want to show long-term appreciation? Help drivers grow.

  • Offer free or discounted CDL endorsements
  • Offer financial wellness workshops
  • Match contributions to a retirement fund
  • Host monthly “driver town halls” to hear feedback and take action

Pro Tip: Consider offering health incentives—like gym memberships or access to telehealth services. They show you care about the long haul.

5. Better Insurance & Benefits (Yes, We Said It)

Let’s get real; benefits matter. And not just health coverage. Drivers care about:

  • Affordable coverage for family members
  • Mental health support
  • Disability and life insurance
  • Occupational accident policies (especially for owner-operators)

Pro Tip: We specialize in building insurance packages that work for both employers and drivers. Whether you manage a fleet of 5 or 500, we’ll help you tailor something that shows your drivers you’ve got their backs on and off the road.

6. Food. Actual, Good Food.

Taco Tuesday in the terminal? Fine. But how about partnering with local food trucks, bringing in catered BBQ, or giving drivers a per diem for their favorite restaurant during appreciation week?

Pro Tip: Ask your drivers their favorite spots ahead of time and surprise them with a gift card to that place. It's a small thing that shows you’re paying attention.

The Bottom Line

Driver Appreciation Week shouldn’t be about checking a box. It’s your chance to build loyalty, boost morale, and remind the people behind the wheel that they’re seen, respected, and valued.

At Transtar Insurance Brokers, we believe safe drivers are happy drivers, and happy drivers stick around. If you want help creating a stronger benefits package, covering more of what matters, or just making sure your risk management doesn’t fall asleep at the wheel, we’re here to help.

Need help upgrading your benefits program before Appreciation Week hits?
Contact us to chat with a Transtar advisor.

Let’s make 2025 the year your drivers feel truly appreciated, not just handed a cheap pen.

Transtar Insurance Brokers
August 1, 2025