1099 CDL Driver Jobs in Massachusetts February 2026

Thompson Transportation Inc

Company CDL-A OTR Driver | Home Every Weekend

Hiring in Massachusetts and 46 other locations
Weekly
$0.50 Per mile

Minimum CDL driver pay starts at $.50 but could be higher based on CDL driving experience.
Quarterly truck driver safety bonus of $.02 added to all miles driven within the quarter.
Truck Driver averages 2,500 miles per week. 401k plan with employer match. Holiday pay.

CDL DNA

CDL A - Company Driver - 1099 - Flat Rate

Hiring in Massachusetts and 25 other locations
2 weeks out, 3 weeks out
$0.63 - 0.67 Per mile
/
$290 Per day

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.
Real Trucking is a highly reputable carrier with a fleet of over 300 trucks.

W2 and 1099 Positions Available

Professional Work Environment

Fully Loaded Trucks

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
Trucks are 2022-2023 Freightliners with 100k-400k miles
Dispatchers will try to maximise your weekly gross working with the spot market and their direct contracts with brokers.

$0 Down, No Credit check

Only for experienced drivers

All charges and trailer included in %

Marvin Keller Trucking

CDL A Driver | Lease - Purchase Owner Operator

Hiring in Massachusetts and 46 other locations
Flexible
$120,000 - 150,000 Per year

Experienced & Knowledgeable Mentors & Support Staff.
Reached Milestones of 30 Lease Purchase Contractors in 2023.
Fleet Specs to Keep Safe & Costs Low. Latest Technology.

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.
Zero Money Down. No Credit Check. Walk Away if the Program isn't Working for You.

Duka Transportation, Inc.

OTR Flatbed Owner Operators

Hiring in Massachusetts and 46 other locations
Flexible
$300,000 - 360,000 Per year

Top 30% of our drivers earn $320,000 or more gross annually
Save on the fuel pumps - Company fuel cards with discount
Be home weekly or every other week

GN GROUP INC

OTR CDL A Reffer Driver | 70CPM

Hiring in Massachusetts and 46 other locations
Flexible
$0.60 - 0.70 Per mile

GN GROUP INC experienced REEFER transportation company is looking for safe CDL class A truck drivers!
Solo Drivers starting at $0.60-$0.70 Cent Per mile. Pay: $1,500.00 - $2,800.00 per week.
CDL - Class A License. Verifiable 2 years of recent OTR Experience.

Jeep Transport LLC

CDL A Company Driver | OTR, Regional, Dedicated

Hiring in Massachusetts and 46 other locations
2 weeks out, 3 weeks out
$0.60 Per mile

Pay: $0.60c/ per mile. Miles Per Week: 2500-3500 mi
Equipment: 2020-2024 automatic Freightliner Cascadia
Pets Friendly. APU, Fridge, Power Inverter in trucks

Dedicated Local and Regional Runs

CDL DNA

CDL A Independent Contractor 1099 | 70-75 CPM

Hiring in Massachusetts and 46 other locations
3 weeks out
$0.70 - 0.75 Per mile
/
30 - 33% Of gross

30% - 33% of gross revenue. Average gross $6,000 - $7,500/week
Cash advances are available to you as long as you are under the load
We will keep you busy while you're on the road

TPA Cargo Solutions LLC

CDL A Owner Operator | $4,000-5,000 take-home

Hiring in Massachusetts and 46 other locations
Flexible
85% Of gross

Personal dispatcher. No forced dispatch
Drop & hook, live load & live unload loads
No touch freight. 24/7 support. Consistent back to back loads

Consistent Back To Back Loads

$4,000-$5,000 Weekly Take-home

Professional No Forced Dispatch

CDL DNA

CDL A Strong Company Driver 1099 - Drop & Hook

Hiring in Massachusetts and 46 other locations
4 weeks out
$0.65 Per mile

We are looking specifically for drivers who can run a lot of miles and stay out for 4 weeks at the time
We have a great variety of trucks from 2022 to 2024 year models
Drivers that are willing to run make $2,500 - $3,200 per week

Only For Strong Solo Drivers

$2,500 - $3,200 Per Week

Drop & Hook Loads

Fox Carriers

Class A Dry Van Owner Operator

Hiring in Massachusetts and 47 other locations
Flexible
92% Of gross

You choose what time to work. 24/7 Driver Support
Possibility to earn up to 92% of gross per week
Emergency Road Repair Advances

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

7,000-8,000 MILES A WEEK for TEAM DRIVERS
We pay all miles, empty and loaded.
We are a small fleet carrier but with a solid background partnership with customers for years

Dedicated Trucking Solutions

Regional CDL A Truck Driver- Online Orientation

Hiring in Massachusetts and 47 other locations
Flexible
$80,000 - 87,000 Per year

Morning start times - between 0500 - 0900. Averages projected at $80,000-87000 per year, touch freight
Drivers will not be delivering on Thanksgiving. they should be able to get home at a reasonable time that day.
Health Savings Account option, Flexible Spending Account, Paid Basic life, Paid Basic accidental death and dismemberment.

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).
Weekly payment, no hidden fees - you get paid your rate fully.

1099 CDL driver jobs in Massachusetts