Why Is Landscaping Insurance So Expensive? 7 Reasons Maryland Contractors Pay More Than They Should

If you're a landscaper in Maryland, you've probably looked at your insurance premium and thought, “Why is this so expensive?”

You're not alone—and you're not crazy.

I work with landscaping contractors across the state, and almost every week someone asks me the same thing. So let’s walk through seven specific reasons why landscaping insurance costs more than you think, and what you can do about it.

Whether you’re mowing lawns, building patios, or cutting down trees, this post is for you.

1. You're in a High-Risk Industry

First, let’s get one thing straight: landscaping is considered a high-risk business by insurance companies.

You’ve got workers doing physical labor with sharp tools, heavy equipment, and dangerous machinery. You’re driving in heavy traffic and towing trailers.  You’re climbing ladders, digging trenches, and sometimes even cutting down trees.

All of those things create risk—a lot of it.

If an insurance company has to pay for:

• A worker’s injury

• Damage to a client’s property

• A lawsuit for negligence

• A stolen skid steer or damaged trailer

…it’s going to cost them. And that cost gets passed on to you in the form of higher premiums.

2. The Type of Work You Do Matters (A Lot)

Not all landscapers are priced the same.

If you’re just mowing lawns and trimming bushes, your risk class is relatively low. But if you're doing hardscapes, tree removal, excavation, or snow plowing, that puts you into a completely different risk category.

In fact:

• Tree removal is often treated more like forestry work.

• Hardscapes (like retaining walls and patios) are treated like masonry contracting.

• Excavation and digging? Those trigger underground utility risk concerns.

  
  

Each of those services carries its own class code—and each class code carries its own price tag.

Solution: If you're offering higher-risk services, make sure you're charging your customers accordingly. Build your insurance costs into your pricing model so you’re not absorbing the hit alone.

3. Seasonal Work and Uninsured Contractors

Landscaping is a seasonal business. In the spring and summer, you’re slammed. In the winter, you might be laying off workers or switching to snow removal.

That kind of unpredictability creates problems with:

• Payroll estimation

• Workers’ compensation audits

• Coverage for short-term hires or 1099 contractors

Let me be real with you here—hiring uninsured subcontractors is one of the fastest ways to blow up your workers’ comp premium. You think you're saving money by using 1099s, but if they don’t carry their own comp, you’re on the hook for it.

And when the year-end audit comes? You’re hit with a surprise bill.

Solution: Require certificates of insurance from all subcontractors before they start work. Better yet, consider a “pay-as-you-go” workers’ comp plan that adjusts in real-time based on your actual payroll.

4. Audit Adjustments Can Crush You

There are two major ways landscapers get burned on insurance audits:

1. Uninsured subs, like we just mentioned.

2. You had a better year than expected.

   
   

If your revenue or payroll grows during the year, your insurance company will come knocking after your policy ends. You might owe 20–30% more than your original quote—and it’s all due in a lump sum.

Solution: Be proactive. Review your payroll and revenue about 90 days before renewal. If you're trending higher than you estimated, update your numbers with your broker. Or set up monthly premium billing based on actual payroll.

This keeps surprises—and sticker shock—to a minimum.

5. More Assets = More Premiums

You’ve probably got:

• Trucks

• Trailers

• Skid steers

• Zero-turn mowers

• Excavators

• Rental equipment

Each one of these assets needs its own coverage. And the more stuff you have, the more coverage you need.

It’s easy to let that coverage get scattered—some on a personal auto policy, some on a business auto, some on rental agreements—and it ends up costing you more in the long run.

Solution: Bundle your assets under one commercial policy that’s designed for landscape contractors. Look for equipment floaters, hired/non-owned auto coverage, and borrowed equipment coverage that fits your needs.

6. You're Not Matched With the Right Insurance Company

Here’s something most landscapers don’t realize:

Just because a company insures “landscapers” doesn’t mean they insure your type of landscaping.

You might get a policy that works for lawn maintenance, but not for:

• Tree work

• Snow plowing

• Retaining walls

• Grading or excavation

  
  

So what happens? You think you’re covered… until something goes wrong. And that’s when you find out there’s a gap in your coverage.

Solution: Work with a broker who understands the full range of services you offer. Your insurance company needs to match not just your business type, but your actual operations.

7. Poor Service Costs You Money

This one is often overlooked but incredibly important.

If it takes your insurance agent days to send a certificate of insurance to a general contractor, you can’t start the job.

That delay?

• Pushes back your work schedule

• Delays payment

• Damages your reputation

Bad service is expensive—even if the premium is cheap.

Solution: Choose a broker who prioritizes responsiveness and accuracy. You need someone who can deliver what you need, when you need it—especially during peak season.

Final Thoughts: What You Can Do About It

Yes, landscaping insurance in Maryland is expensive—but it doesn’t have to be unmanageable.

Here’s what you can do to get control of your costs:

• Price your services to match your risk

• Require COIs from subcontractors

• Set up pay-as-you-go billing to avoid audits

• Review your operations and class codes with a broker who actually understands landscaping

• Consolidate your coverages under one policy built for your business

• Work with someone who delivers excellent service and communicates clearly

Need Help Making Sense of Your Insurance?

I specialize in helping Maryland landscaping contractors build insurance programs that actually fit their business—without overpaying or being underinsured.

If you’re tired of getting burned on audits, confused by your coverage, or frustrated by bad service, I’d love to help.

👉Submit a form below to set up a time to talk. 

And remember—uninsured claims are always more expensive than insurance. Make sure your coverage is built to keep your business moving forward.