1099 CDL Driver Jobs in Massachusetts May 2026

CDL DNA

NEW TRANS GROUP LTD

Hiring in Massachusetts and 46 other locations
3 weeks out, 2 weeks out
$65.00 - 67.00 Per mile

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High Miles

New Equipment

No Payment Delays

Xcalibur Logistics

CDL Pick-up Company Driver - Hotshot Car Hauling

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

Competitive Compensation: Earn $2,000-2,500+ per week
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

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

A&V Cargo Inc

Small Fleet Is Hiring A Company Driver

Hiring in Massachusetts and 46 other locations
2 weeks out
30% Of gross
/
$0.60 Per mile

Small fleet is hiring. Flatbed trailer - we will haul everything that will fit on a 53ft flatbed.
Running all over Midwest, South and South East
Forwarding all rate confirmations. We offer a respectful and fair treatment, on-time salary and all around support!

Owner Operated Small Company

Full Transparency

Keep Trucking LLC

OTR Flatbed/Stepdeck CDL-A Company Driver | 1099 Position

Hiring in Massachusetts and 46 other locations
Flexible
$0.70 Per mile
/
25% Of gross

Drivers Average $1,750 - $2,450 Weekly Gross. CPM $0.70 or 25% for the Load for Flatbed. Cash Advance.
All miles are paid Empty & Loaded. Extra Stops($50). 2022 and Newer Volvos, and Peterbuilts. Rider and Pet friendly
Get Paid Every week via Direct Deposit. Drivers can Switch beetween divisions and get paid either by % or CMP.

Ashley Distribution Services LTD

Regional OTR CDL-A Truck Driver | $81,000/year

Hiring in Massachusetts and 46 other locations
Weekly
$81,000 Per year

Top 25% of drivers earn $81,000 annually. Regional routes. Regular 34-hour resets at home. No-touch freight.
Mix of live load/unload and drop and hook accounts. Consistent, high weekly miles. Excellent, premium equipment.
Generous benefits package: Can add up to an additional 27% on top of your base salary! Job stability.

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

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 OTR Dedicated Team Drivers - 80 CPM

Hiring in Massachusetts and 43 other locations
3 weeks out
$4,000 - 4,600 Per week
/
$0.75 Per mile

We can match you with another driver
2023-2024 Kenworth, Peterbilts trucks
We allow pets. No check hold

$2,000 - $2,300 per driver flat

Dedicated Lanes

2023-2024 Trucks

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
Average owner operator gets a paycheck of $4,000-$5,000 per week after all expenses

Consistent Back To Back Loads

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

Professional No Forced Dispatch

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
Operating in Midwest and West Coast

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

3,500-4,000 MILES A WEEK for SOLO
We pay all miles, empty and loaded.
Weekly Settlements.

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
Weekly Settlements via ACH. 401k & 401k match. Profit sharing

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.
Minimum inside dimensions of the cargo area 100x50x50 inches (L x W x H).
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

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

1099 CDL driver jobs in Massachusetts