1099 CDL Driver Jobs in Massachusetts October 2026

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
Be part of a team that values hard work, professionalism, and a supportive environment
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

Two day fast PAID orientation
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

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.
Zero Money Down. No Credit Check. Walk Away if the Program isn't Working for You.
Competitive Pay. Excellent Benefits. Consistent Freight.

U.S. Xpress, Inc.

CDL Class A Team Drivers

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

Your team can average $200,000 or more!
Medical, Dental, Vision, and 401k Match.
Average 5,000 miles per week or more.

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

Hittman Transport Services, Inc.

Owner Operators CDL A Team Truck Drivers

Hiring in Massachusetts and 46 other locations
Daily, Flexible
$10,000 Per week

Hittman Transport Services, Inc. is contracting owner operators.
Teams make up to $10,000 weekly. Quarterly Fuel Discount, plus Discounts at the pump.
Hittman Transport pays for the yearly expenses: tolls, fuel tax, tractor washes...

Just Trucking Services

Class A Independent Contractors 1099

Hiring in Massachusetts and 46 other locations
2 weeks out
$2,200 - 2,400 Per week

Steady weekly take home $
At least 3,000 weekly miles. 2-3 out weeks & 3-4 days at home (flexible)
Welcome Independent contractors to join our small family owned company

Small Family Owned Fleet

Flexible Dispatch

$2,200+ per week

CDL DNA

CDL A Team Drivers for Amazon Loads - Flat Rate

Hiring in Massachusetts and 46 other locations
4 weeks out
$1,900 Per week
/
$0.75 Per mile

Most of the loads are DROP-N-HOOK
We have a great variety of trucks from 2022 to 2024 year models
We can give you north of 6,000 mi per week

$1,900 Weekly Flat Rate

Drop & Hook Loads

Team Matching Available

Sinbex Dispatch LLC

Owner Operators & Fleet Owners | Power Only

Hiring in Massachusetts and 47 other locations
Weekly
$5,000 - 10,000 Per week

Transparency is key, and the moto we live by
Load booking, Rate negotiating, Signing rate confirmations and broker-carrier packets
Fixed commission fee. Welcome small fleet owners

Jahany Transportation Logistics LLC.

CDL A Dry van Owner Operator Hazmat Required

Hiring in Massachusetts and 47 other locations
Weekly
$8,000 - 12,000 Per week

90/10 Split: You Keep the Majority of Your Earnings!
Trailer Rent: $250 per week (if you don't own a trailer)
Save on fuel with our fuel card, offering discounts of up to 60 cents per gallon

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.
Clean and tidy vans are preferred - no debris, spots, dents, etc.
Weekly payment, no hidden fees - you get paid your rate fully.

Pelts Xpress

CDL A Owner Operator | Regional Runs

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

$250/week - Dry Van Rental. Get a FREE trailer for 1 month!
88% of gross revenue. Up to $0.40 fuel discount (100% to the owner)
20+ years experience in dispatching. Abundant Freight

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
We currently have 2024 new trucks for you to run.
LIL Trucking will make sure you aren't sitting around and waiting for loads. Apply now!

3,500+ Miles Per Week

2024 Brand New Trucks

CDL DNA

CDL A Strong Solo Drivers - 1099 | Only 3 months of experience

Hiring in Massachusetts and 46 other locations
3 weeks out
$0.63 - 0.70 Per mile

We have enough work for even the most hardworking drivers, so miles will be high and consistent!
We have driver assistants that speak Spanish available at all times.
We only ask for basic English knowledge to communicate with dispatchers, warehouse workers and DOT officers.

Welcome Strong Solo Drivers

Large Latino Drivers Community

Get A Lot Of Miles

1099 CDL driver jobs in Massachusetts