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Workers’ Compensation Risks for Southold Landscaping and Property Maintenance Businesses

Workers’ Compensation Risks for Southold Landscaping and Property Maintenance Businesses

Nov 04, 2026

Workers' Compensation Insurance

Worker grimacing in pain after workplace injury

If you run a landscaping or property maintenance business in Southold with even one employee, New York almost certainly requires you to carry workers' compensation. That includes part-time and seasonal crew members. Workers' compensation for landscaping businesses matters more than it does in most trades because the work combines power equipment, vehicles, ladders, chemicals, and long days outdoors. One serious injury on an uninsured crew can cost more than a full season of revenue.

Landscaping on the North Fork has its own rhythm. Spring cleanups, weekly mowing on estate properties, hedge and tree work through the summer, fall leaf removal, and caretaking for second homes once summer residents close up for the season. Each season brings different hazards, and your coverage needs to keep up with all of them.

New York's Workers' Compensation Requirements

The New York State Workers' Compensation Board states that "virtually all employers in New York State must provide workers' compensation coverage for their employees." Under the Board's rules, that requirement covers:

  • Part-time employees
  • Family members who work in a for-profit business, whether paid or unpaid
  • People "volunteering" for a for-profit business, who the Board treats as employees
  • Borrowed, leased, and temporary workers

Sole proprietors and partnerships with no employees aren't required to carry it, though they can choose to. The moment you hire a helper for the summer, the rules change.

New York employers with one or more employees on at least 30 days in a calendar year also need disability benefits and paid family leave coverage, according to the Workers' Compensation Board. That's a separate requirement from workers' comp, and it's easy to overlook when you're adding seasonal staff.

The Biggest Injury Risks for Landscaping Crews

The U.S. Bureau of Labor Statistics reported 12,380 nonfatal injury and illness cases requiring days away from work among landscaping and groundskeeping workers in private industry in 2019, with sprains and strains, soreness and pain, and cuts and lacerations leading the list (BLS). The same data shows transportation incidents, falls, contact with equipment, and exposure to harmful environments as the leading causes of fatal injuries in this occupation from 2015 through 2019.

Here's how those risks show up day to day on the East End.

Mowers, Trimmers, and Chippers

Riding mowers on sloped lawns, string trimmers throwing debris, hedge trimmers, chainsaws, and wood chippers all cause serious injuries every year. Cuts, amputations, and eye injuries are common, and a rollover on a steep bank near the water can be life-altering.

Ladders, Lifts, and Tree Work

Pruning tall privet hedges, cleaning gutters for caretaking clients, and trimming trees all put workers at height. Falls are among the costliest workers' comp claims because recovery times tend to be long.

Heat, Sun, and Long Summer Days

July and August are peak season on the North Fork, and crews often work full days in direct sun. Heat-related illness can develop quickly, especially for new or returning seasonal workers who haven't adjusted to the conditions.

Chemicals and Treatments

Fertilizers, pesticides, and herbicides can cause skin, eye, and respiratory problems if they're handled or applied without proper protection.

Driving Between Job Sites

Crews spend a large part of the day on the road with trucks and trailers, moving between properties on Route 25 and Route 48. Transportation incidents are a leading cause of fatal injuries in landscaping, which is why commercial auto coverage should be part of the conversation alongside workers' comp.

Repetitive Strain and Lifting

Hauling mulch, stone, and debris day after day leads to back injuries and repetitive strain. These claims may seem minor at first but can turn into lengthy time away from work.

The Subcontractor Trap

Many landscaping businesses bring in subcontractors during busy stretches, such as a tree service, an irrigation installer, or extra hands for fall cleanups. Under New York Workers' Compensation Law Section 56, a contractor who subcontracts work can be held liable for compensation to a subcontractor's injured employee if the subcontractor hasn't secured coverage.

The Board also notes that many sole proprietors working as subcontractors have been found to be employees after they were injured. That's why it's standard practice to collect a current certificate of workers' compensation insurance from every subcontractor before they set foot on a job. Our post on workers' compensation for self-employed and independent contractors goes into more detail.

What Going Without Coverage Can Cost

The penalties in New York are steep. According to the Workers' Compensation Board:

  • An employer without coverage for 10 or more consecutive days can face a penalty of up to $2,000 for each 10-day period of noncompliance.
  • Failing to cover more than five employees within a 12-month period is a class E felony, with a fine of $5,000 to $50,000.
  • The Board can issue a stop work order that halts all business activity.
  • An uninsured employer is responsible for all wage and medical benefits awarded to an injured employee, plus legal costs.

For a small landscaping company, a stop work order in the middle of June could be as damaging as the penalty itself.

Ways to Manage Your Workers' Comp Costs

Workers' comp premiums are based largely on payroll and the risk classification of the work your employees do, and your claims history affects future pricing. For a closer look at the formula, see how workers' compensation premiums are calculated.

A few habits can help keep costs and claims in check:

  • Classify employees accurately. Office staff and field crews are typically rated differently, so make sure payroll is reported under the right classifications.
  • Train on equipment every season. Refresher training for returning seasonal workers can prevent the same injuries from repeating year after year.
  • Require protective gear. Eye and hearing protection, gloves, and sturdy footwear reduce common injuries.
  • Plan for heat. Build in water, shade, and rest breaks during the hottest part of the day.
  • Report injuries promptly. Quick reporting helps the claim move smoothly. Our guide to the workers' compensation claims process in 7 simple steps walks through what happens next.
  • Ask about payment options. Seasonal businesses with payroll that swings up and down may benefit from pay-as-you-go workers' compensation, which bases payments on actual payroll.

Protect Your Crew and Your Business

Workers' compensation for landscaping businesses is about more than meeting a state requirement. It protects your employees when they get hurt and protects your business from a claim that could put you out of operation. East End Insurance Agency has been insuring the East End of Long Island since 1885, and we understand how seasonal businesses on the North Fork operate. We can review your payroll, classifications, and subcontractor practices, and help you pair workers' comp with the commercial liability, commercial auto, and commercial umbrella coverage your business may need.

For personalized assistance and a free quote, contact us today at East End Insurance Agency. You can also give us a call at 631-765-3811.

Frequently Asked Questions

1. Do landscaping businesses in New York need workers' compensation insurance?

Yes, if they have employees. New York requires virtually all employers to carry workers' compensation, including coverage for part-time workers and most family members who work in the business. Sole proprietors with no employees aren't required to carry it.

2. Do I need workers' comp for seasonal landscaping workers?

Yes. Seasonal and part-time employees are covered under New York's workers' compensation requirements the same way full-time employees are.

3. Am I responsible if my subcontractor's worker gets hurt?

You can be. Under New York law, a contractor may be liable for workers' compensation benefits if an uninsured subcontractor's employee is injured. Collect a certificate of insurance from every subcontractor before work begins.

4. What happens if I don't carry workers' comp in New York?

The Workers' Compensation Board can assess penalties of up to $2,000 for every 10 days without coverage, issue a stop work order, and hold you responsible for the injured worker's medical and wage benefits.