W2 CDL Driver Jobs in Massachusetts January 2026

Trimac Transportation Inc

OTR CDL-A HazMat Company Driver | Up to 75 CPM

Hiring in Massachusetts and 46 other locations
3 weeks out
$0.75 Per mile

Drivers are out 3 weeks. Pick up points : Various locations in the US & Canada. 2500-3000 miles a week.
Medical, dental, and vision insurance. Employee Assistance Program. Life insurance, disability insurance.
Flexible Spending Accounts. 401 (K) Profit sharing with company match. Consistent, year-round work.

Estes Express Lines

Regional CDL-A Driver | Fully Endorsed | 74-80 CPM

Hiring in Massachusetts and 4 other locations
Flexible
$0.74 - 0.80 Per mile

Starting mileage rate of 74 - 80 CPM. Schedule - Night Shift. Two weeks paid time off plus holidays.
Short- and long-term disability plans; life and AD&D insurance. Employee disaster relief fund.
Financial wellness program. Employee discount benefit program. Safety and referral bonus eligibility.

Leggett & Platt Inc

OTR CDL-A Truck Drivers | $75K - $90K Per Year

Hiring in Massachusetts and 46 other locations
2 weeks out
$75,000 - 90,000 Per year

Drivers average $75K Per Year & Top 10% are averaging $90K. 2-Day Paid Orientation.
Quarterly Safety & Performance Bonuses Start Day 1! Passenger & Pet Friendly. 9 Paid Holidays
Tenure Pay Starting at 6 Months of Service. Medical, Dental, Vision, and Life Insurance.

Killpack Trucking Inc

CDL-A Solo & Team Drivers | Home every week

Hiring in Massachusetts and 46 other locations
Weekly
$0.47 - 0.54 Per mile

Pay: $0.47 - $0.54 per mile. 3600 to 3800 miles per week. No forced dispatch.
Insurance benefits. Dedicated freight. Paid after every trip. 401(k). Dental insurance.
Health insurance. Paid time off. Vision insurance. Detention pay. Layover pay. Extra stop pay.

MLC LLC

OTR Class A Truck Driver | 65 CPM

Hiring in Massachusetts and 46 other locations
Weekly
$0.65 Per mile

Pay: From $0.65 per mile. Average 2,500 to 3,000 miles/week. 401(k) matching.
Dental insurance. Employee assistance program. Health, Life insurance.
Paid orientation. Paid time off. Tuition reimbursement. Vision insurance.

Countryside Auto Transport Inc

OTR CDL-A Car Hauler | Up to $100,000+/year

Hiring in Massachusetts and 46 other locations
Flexible
$75,000 - 100,000 Per year

Up to $100,000+/year (includes CPM, per diem, pay per car). +0.10 for east coast miles. +$20.00 per car loaded.
Routes: NO Northwest and New York City. Late Model Equipment. All automatics. Full Benefit Package.
Insurance: Health, Dental, Life, Vision, Short-term disability. 401K, Employer match. Vacation Pay.

CDL DNA

CDL A - Company Driver OTR W2

Hiring in Massachusetts and 25 other locations
2 weeks out, 3 weeks out
$0.60 - 0.63 Per mile

As a driver for Real, you will enjoy a stable work, predictable paycheck and full package of benefits.
We provide you with a fully loaded 2021-2024 Freightliner Cascadia equipped with a refrigerator, microwave, inverter, APU, mattress, and tablet.
Our goal is to ensure that our drivers are safe, comfortable, and well-compensated.

W2 and 1099 Positions Available

Professional Work Environment

Fully Loaded Trucks

Heartland Express

CDL-A Regional Truck Driver | Dry Van No Touch

Hiring in Massachusetts and 46 other locations
Weekly
$67,000 - 94,000 Per year

$67,000 $94,000 depending on location.
Paid Orientation / Training. Paid Vacation.
Health, dental, vision and life insurance.

Buchanan Hauling & Rigging, Inc.

CDL A Dry Van Company Driver

Hiring in Massachusetts and 46 other locations
Weekly
$0.75 Per mile

Team Drivers Welcome. 24/7 Team Support for ANY needs.
Major Holidays OFF & PAID. Health Benefits. W2.
Trucks equipped w/ Inverters, APU’s, Fridge, Nice & Cleaned, and New Mattress

Riverside Transport Inc.

OTR CDL-A Company Driver - Dry Van

Hiring in Massachusetts and 46 other locations
2 weeks out
$0.58 - 0.62 Per mile

Earn $0.58 - $0.62 per Mile Based on Experience.
100% No Touch, Dry Van Freight. Home Every 2 Weeks.
Medical, Dental, Vision and Life Insurance. Paid Time Off.

D Rig Trucking, Inc.

Solo Owner Operator Driver | 12,000/week

Hiring in Massachusetts and 46 other locations
Flexible
$12,000 Per week

Pay: $12,000.00 per week
Expected hours: No more than 70 per week
Benefits: 401(k). 401(k) matching. AD&D insurance. Dental insurance

Jim Lawrence Transportation, Inc.

Owner Operators OTR CDL A Truck Driver

Hiring in Massachusetts and 46 other locations
Weekly, Flexible
$100,000 - 290,000 Per year

Pay: $100,000.00 - $290,000.00 per year.
Benefits: Dental insurance, Health insurance, Referral program, Vision insurance
Drivers are home most weekends. No forced dispatch

Oriole Transportation

CDL-A Truck Driver | Dry Van | No Touch

Hiring in Massachusetts and 47 other locations
2 weeks out
$1,375 - 1,665 Per week

Medical, Dental, Vision, and Life Insurance
Paid orientation and job-specific training
401K with company match. Paid vacation and holidays

Blackwell's Trucking Inc.

Regional Dry Van CDL A Drivers

Hiring in Massachusetts and 47 other locations
Weekly
$1,300 - 1,575 Per week

Layover/Detention Pay
5% Live Loads at receiver location
Steady customer interaction on daily bases

CDLhire

Dry Van Truck Drivers Earn up to 100,000

Hiring in Massachusetts and 47 other locations
Weekly
$100,000 Per year

Weekly Safety Bonus, Mileage Bonuses and DOT inspection bonuses
6 Paid Holidays a Year
Company Covered Life insurance policy

W2 CDL driver jobs in Massachusetts