1099 CDL Driver Jobs in Massachusetts September 2025

Xcalibur Logistics

CDL Pick-up Company Driver - Hotshot Car Hauling

Hiring in Massachusetts and 46 other locations
Flexible
$2,000 - 2,500 Per week

Experienced Dispatch: Our dispatchers are former drivers, so they understand your needs
24-Hour Road Support & In-House Repair Shop
Top-Notch Equipment: Most of our trucks and equipment are brand new

Legal Miles

Only 3-4 Car Hauling

Small Owner Operated Fleet

C1 Transportation Inc

CDL A Flatbed OTR Driver

Hiring in Massachusetts and 45 other locations
Flexible
30% Of gross

2021-2025 Volvo, Freightliner, International and Kenworth's
Direct Deposit weekly, payments should be received by Friday each week.
8 driver maximum per one dispatcher, which allows our dispatchers to pre-plan loads for you.

Steady Weekly Paycheck

Paid Orientation

Pre-planned Trips

CRST The Transportation Solution Inc

CDL-A Flatbed Owner Operator | Solo or Team

Hiring in Massachusetts and 46 other locations
Flexible
75% Of gross

Owner Operator Options. Solo or Team positions. Paid Up to 75% of the Gross revenue of each load. Weekly Payroll.
Flatbed securement training program available. Fleet Manager Assistance Option or Run On Your Own.
Manual and Automatic transmissions. Variety of Trailer Rental Options. Retention Bonuses available. Pick your Own Loads.

CDL DNA

CDL A - Lease Purchase & Rental Program - $0 Down

Hiring in Massachusetts and 46 other locations
2 weeks out
78 - 80% Of gross

Lease Rental or Lease Purchase program for experienced drivers
Dispatchers will try to maximise your weekly gross working with the spot market and their direct contracts with brokers.
You only pay for truck, fuel, and tolls.

$0 Down, No Credit check

Only for experienced drivers

All charges and trailer included in %

Royal Trucking Company

Lease CDL A OTR Truck Driver

Hiring in Massachusetts and 46 other locations
Flexible
$78,000 - 100,000 Per year

Dry Van Trainees : Up to $58K Year. Dry Van Experienced Drivers : $72K-$78K Yearly.
Flatbed Trainees : $61K Year. Flatbed Experienced Drivers : $85K-$100K Yearly.
Competitive Pay. Excellent Benefits. Consistent Freight.

Innfinity Logistics Inc

CDL A Lease To Purchase | Dry Van/Reefer/Flatbed

Hiring in Massachusetts and 46 other locations
3 weeks out
$2,000 - 5,500 Per week

$2,000- $3,500 Dry Van & Reefer solo drivers.
$2,700 - $5,500 Flatbed solo drivers.
24/7/365 Support (Fleet, Safety, Dispatch, Afterhours)

U.S. Xpress, Inc.

CDL Class A Team Drivers

Hiring in Massachusetts and 46 other locations
Weekly
$200,000 Per year

Medical, Dental, Vision, and 401k Match.
Extra cash for every doubles lead.
Great equipment average 18 months.

Transurfing Inc

CDL A Reefer & Dry van Company Driver OTR

Hiring in Massachusetts and 46 other locations
3 weeks out
$0.63 - 0.65 Per mile
/
28 - 30% Of gross

2021 - 2023 Kenworth T680 with automatic transmission
We have a lot of customer freight and need professional, responsible and safe drivers to help us move it
If you are looking for a consistent job, you are welcome to apply

Only For Safe and Responsible Drivers

Great New Trucks & Equipment

Consistent Direct Freight

Total Domination Inc

CDL A OTR Hazmat drivers Dry Van only

Hiring in Massachusetts and 47 other locations
Weekly
$0.70 - 0.75 Per mile

We pay all miles, empty and loaded.
Weekly Settlements.
Direct deposit to bank account

I&A LOGISTICS LLC

CDL A Owner Operator

Hiring in Massachusetts and 47 other locations
Flexible
88% Of gross

For driver with TWIC card we work with UIIA, so the payment is much more higher
Working with VIP brokers. Our drivers are doing up to 9 to 12k.
Company fee 12% from total gross. Available amazon load board with 100% performance

Integrity Gas Services LLC

Regional or OTR Class A CDL Drivers

Hiring in Massachusetts and 47 other locations
Flexible
$23 Per hour

Integrity Gas Services is looking for safe company drivers to run regional or OTR
Pay $23/hour with overtime paid at time and a half after 40 hours. $50 per day per diem
Employer sponsored medical, dental, vision & group term life insurance

Odysseia

CDL C Sprinter Van / Cargo VanOwner Operator

Hiring in Massachusetts and 47 other locations
Weekly
$1,000 Per week

No authority; NO MC. Be ready to make long-distance/other loads; local - rarely and occasionally.
Own a Cargo van/Sprinter van (2010 and newer, NO rental vehicles).
Clean and tidy vans are preferred - no debris, spots, dents, etc.

Pelts Xpress

CDL A Owner Operator | Regional Runs

Hiring in Massachusetts and 46 other locations
Flexible
88% Of gross

Consistent direct customer freight, both Regional and OTR!
Flexible dispatch adjusted to your preference. Solo & Team loads
Assistance with Plates & Registration. Warm and welcoming team

FREE 30 Days Trailer Rent

Up to $0.40 fuel discount (100% to the owner)

Plates & Registration Program

LIL Trucking Inc

CDL A Reefer Company Drivers 1099

Hiring in Massachusetts and 46 other locations
2 weeks out
$0.68 Per mile
/
30% Of gross

Main directions: Midwest > Portland, Seattle. West Coast > Midwest / East coast
Drive up to 3,500mi or more! Most of our drivers make $2,200+ per week.
We currently have 2024 new trucks for you to run.

3,500+ Miles Per Week

2024 Brand New Trucks

CDL DNA

CDL A Dedicated Reefer Driver - Weekly Home

Hiring in Massachusetts and 7 other locations
Weekly
$1,800 Per week

We have a few dedicated contracts going from Chicago area to New England region. 2-3 picks in Chicago and 2-3 drops in Connecticut/Massachusetts/Main/Vermont etc.
If you are interested in this Reefer Dedicated position, please press Apply Now!
We can get our drivers home every weekend consistently.

$1,800 Weekly FLAT RATE

Dedicated Routes

Be Home Every Weekend

1099 CDL driver jobs in Massachusetts