Owner Operators Jobs, Employment in Pittsfield,MA Now Hiring November 2026

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Truck Driver Job Application

CDL-A Owner Operator Truck Driver Jobs ($200k - $325k+ a Yr!) Apply Now!

Hiring Drivers Now

Pittsfield, MA

$200,000-$325,000/yr

Urgently Hiring

Franchise opportunity, not a traditional job.

Mac Tools Franchise Owner – Financial Qualification Required

Mac Tools

Bennington, VT 05201

Month-long training to run your franchise
Your truck, your territory, your customers
Must be willing to complete a credit check

Be part of the largest and fastest growing tool company in the world as a Mac Tools franchise owner.

New, Posted 11 hours ago

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Apply Directly

CDL-A Owner Operator Driver

Forward Air, Inc.

Pittsfield, MA

Requires TravelUrgently Hiring

Earn up to $250,000 gross per year*

Solo Owner Operators earn up to $250,000 gross per year*, with base compensation of $1.31 per loaded mile and $1.18 per empty mile plus FSC*, averaging $4,100 to $5,200 gross per week*, plus additional compensation on all miles based on load destination.

$5,000 paid out within your first year.*

A substantial fuel surcharge program

Drivers are typically out on the road 2 to 3 weeks at a time.

CDL-A

Valid Class A CDL

12+ months verifiable driving experience

Must be 23 years of age

Equipment must be newer than 10 years old

New, Posted 11 hours ago

Recommended

OTR Solo & Team Owner Operators / CDL-A / $4,500 - $10,000 Weekly

TForce Freight

New Lebanon, NY 12125

$4,500-$5,000/wk

Requires TravelUrgently Hiring

Solos - Average $4,500-$5,000/week

Teams - Average $9,500-$10,000/week

2021 and Newer Truck Owners get an Additional $.02 per mile added!

Referral bonus - $2,000 for solo and $5,000 for teams

Empty miles paid at 80% of loaded rate

100% fuel surcharge on all miles

Fast pay - within 24 hours of paperwork receipt

Tolls and scales paid

Fuel Discounts - up to $1 off on all fuel

Excellent Tire Discounts Offered

No trailer fees

PrePass Elite provided

Over the road - typically out 8 to 10 days

CDL-A

Minimum 1 year over the road experience

Must OWN YOUR TRUCK

CDL - A

Doubles and Hazmat endorsements = Top rate pay

New, Posted 11 hours ago

Recommended

OTR Solo & Team Owner Operators / CDL-A / $4,500 - $10,000 Weekly

TForce Freight

Austerlitz, NY 12017

$4,500-$5,000/wk

Requires Travel

Solos - Average $4,500-$5,000/week

Teams - Average $9,500-$10,000/week

2021 and Newer Truck Owners get an Additional $.02 per mile added!

Referral bonus - $2,000 for solo and $5,000 for teams

Empty miles paid at 80% of loaded rate

100% fuel surcharge on all miles

Fast pay - within 24 hours of paperwork receipt

Tolls and scales paid

Fuel Discounts - up to $1 off on all fuel

Excellent Tire Discounts Offered

No trailer fees

PrePass Elite provided

Over the road - typically out 8 to 10 days

CDL-A

Minimum 1 year over the road experience

Must OWN YOUR TRUCK

CDL - A

Doubles and Hazmat endorsements = Top rate pay

New, Posted 19 hours ago

Recommended

Apply Directly

Owner Operator Driver - 75% of Linehaul + 100% FSC

Tennessee Steel Haulers

Pittsfield, MA

$3,000/wk

$5,000 bonus

New, Posted 11 hours ago

Owner Operators / CDL-A / Avg. Weekly Gross $4,300 - $6,000 / 1 Year EXP Req'd

BLAIR

New Lebanon, NY 12125

$5,000 bonus

Requires TravelFlexible Schedule

Avg. Weekly Gross $4,300 - $6,000

Average Weekly Take Home: $1,600-$3,000

Average weekly gross: $4,300-$6,000

Average weekly take home: $1,600-$3,000

$5,000 sign-on bonus

Receive $2,500 after your 1st load

$5,000 referral bonus

Receive $2,000 after your 1st load

$4,300-$6,000

$1,600-$3,000

$3,000 referral bonus

Receive $1,500 after your 1st load

High earnings potential: Earn up to 76% of linehaul revenue

Better pay for bigger operations. Higher percentages for multiple trucks and trailers

Warranty Program Available!

No money down & no credit check

100% of trailer maintenance covered by Blair when pulling Blair's trailer

Warranty program available!

Low weekly payment

Contractors get 100% of the Fuel discounts at the pump

Maintenance, equipment & tire discounts

Must have a valid Class A CDL

Must be at least 22 years old

Must have 1 year of OTR experience in the last 5 years

Must have 6 months of flatbed experience in the last 10 years

No felonies within the last 10 years

Owner Operators can never have failed or refused to submit to a pre-employment or random drug or alcohol test with any employer

Recommended

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Owner Operator Reefer Truck Driving Job in Middletown, CT

Shaffer Trucking

Middletown, CT 06457

$30/hr

OnsiteHealth InsuranceRetirement Benefit

Average Weekly Pay of $4,100 (based on 2900 miles weekly)

Fuel Surcharge* paid on all loaded miles

Guaranteed detention pay at $30/hour

Fuel discount

Free trailer usage

Maintenance available at our terminal's shops

Discounted Parts and Labor

Payment for authorized lumpers, if required

Relicensing Credit for Plates & Permits

EZ Pass provided and reimbursement of authorized tolls

Health Insurance Options

IRA Contributions

Flexible home time

Days on the Road: Varies depending on home location and fleet choice

Recommended

CDL-A Owner Operator Driver Job ($200k - $325k+ a Year!) Quick Apply!

Hiring Drivers Now

Stephentown, NY 12168

$200,000-$325,000/yr

New, Posted 17 hours ago

seasoned.co

Taco Bell - Team Member - Full Time - Pittsfield - Urgently Hiring

Taco Bell

Pittsfield, MA 01201

No ExperienceUrgently Hiring

765 Owner Operators jobs in Pittsfield,MA

CDL-A Owner Operator Truck Driver Jobs ($200k - $325k+ a Yr!) Apply Now!

$200,000-$325,000/yr

Mac Tools Franchise Owner – Financial Qualification Required

CDL-A Owner Operator Driver

OTR Solo & Team Owner Operators / CDL-A / $4,500 - $10,000 Weekly

$4,500-$5,000/wk

OTR Solo & Team Owner Operators / CDL-A / $4,500 - $10,000 Weekly

$4,500-$5,000/wk

Owner Operator Driver - 75% of Linehaul + 100% FSC

$3,000/wk

$5,000 bonus

Owner Operators / CDL-A / Avg. Weekly Gross $4,300 - $6,000 / 1 Year EXP Req'd

$5,000 bonus

Owner Operator Reefer Truck Driving Job in Middletown, CT

$30/hr

CDL-A Owner Operator Driver Job ($200k - $325k+ a Year!) Quick Apply!

$200,000-$325,000/yr

Taco Bell - Team Member - Full Time - Pittsfield - Urgently Hiring

765 Owner Operators jobs in Pittsfield,MA

CDL-A Owner Operator Truck Driver Jobs ($200k - $325k+ a Yr!) Apply Now!

$200,000-$325,000/yr

Mac Tools Franchise Owner – Financial Qualification Required

CDL-A Owner Operator Driver

OTR Solo & Team Owner Operators / CDL-A / $4,500 - $10,000 Weekly

$4,500-$5,000/wk

OTR Solo & Team Owner Operators / CDL-A / $4,500 - $10,000 Weekly

$4,500-$5,000/wk

Owner Operator Driver - 75% of Linehaul + 100% FSC

$3,000/wk

$5,000 bonus

Owner Operators / CDL-A / Avg. Weekly Gross $4,300 - $6,000 / 1 Year EXP Req'd

$5,000 bonus

Owner Operator Reefer Truck Driving Job in Middletown, CT

$30/hr

CDL-A Owner Operator Driver Job ($200k - $325k+ a Year!) Quick Apply!

$200,000-$325,000/yr

Taco Bell - Team Member - Full Time - Pittsfield - Urgently Hiring

765 Owner Operators jobs in Pittsfield,MA

CDL-A Owner Operator Truck Driver Jobs ($200k - $325k+ a Yr!) Apply Now!

$200,000-$325,000/yr

Mac Tools Franchise Owner – Financial Qualification Required

CDL-A Owner Operator Driver

OTR Solo & Team Owner Operators / CDL-A / $4,500 - $10,000 Weekly

$4,500-$5,000/wk

PaySolos - Average $4,500-$5,000/weekPayTeams - Average $9,500-$10,000/weekPayReferral bonus - $2,000 for solo and $5,000 for teams

OTR Solo & Team Owner Operators / CDL-A / $4,500 - $10,000 Weekly

$4,500-$5,000/wk

PaySolos - Average $4,500-$5,000/weekPayTeams - Average $9,500-$10,000/weekPayReferral bonus - $2,000 for solo and $5,000 for teams

Owner Operator Driver - 75% of Linehaul + 100% FSC

$3,000/wk

$5,000 bonus

Owner Operators / CDL-A / Avg. Weekly Gross $4,300 - $6,000 / 1 Year EXP Req'd

$5,000 bonus

PayAvg. Weekly Gross $4,300 - $6,000PayAverage Weekly Take Home: $1,600-$3,000PayAverage weekly gross: $4,300-$6,000

Owner Operator Reefer Truck Driving Job in Middletown, CT

$30/hr

PayAverage Weekly Pay of $4,100 (based on 2900 miles weekly)PayFuel Surcharge* paid on all loaded milesPayGuaranteed detention pay at $30/hour

CDL-A Owner Operator Driver Job ($200k - $325k+ a Year!) Quick Apply!

$200,000-$325,000/yr

Taco Bell - Team Member - Full Time - Pittsfield - Urgently Hiring

765 Owner Operators jobs in Pittsfield,MA

CDL-A Owner Operator Truck Driver Jobs ($200k - $325k+ a Yr!) Apply Now!

$200,000-$325,000/yr

Mac Tools Franchise Owner – Financial Qualification Required

CDL-A Owner Operator Driver

OTR Solo & Team Owner Operators / CDL-A / $4,500 - $10,000 Weekly

$4,500-$5,000/wk

PaySolos - Average $4,500-$5,000/weekPayTeams - Average $9,500-$10,000/weekPayReferral bonus - $2,000 for solo and $5,000 for teams

OTR Solo & Team Owner Operators / CDL-A / $4,500 - $10,000 Weekly

$4,500-$5,000/wk

PaySolos - Average $4,500-$5,000/weekPayTeams - Average $9,500-$10,000/weekPayReferral bonus - $2,000 for solo and $5,000 for teams

Owner Operator Driver - 75% of Linehaul + 100% FSC

$3,000/wk

$5,000 bonus

Owner Operators / CDL-A / Avg. Weekly Gross $4,300 - $6,000 / 1 Year EXP Req'd

$5,000 bonus

PayAvg. Weekly Gross $4,300 - $6,000PayAverage Weekly Take Home: $1,600-$3,000PayAverage weekly gross: $4,300-$6,000

Owner Operator Reefer Truck Driving Job in Middletown, CT

$30/hr

PayAverage Weekly Pay of $4,100 (based on 2900 miles weekly)PayFuel Surcharge* paid on all loaded milesPayGuaranteed detention pay at $30/hour

CDL-A Owner Operator Driver Job ($200k - $325k+ a Year!) Quick Apply!

$200,000-$325,000/yr

Taco Bell - Team Member - Full Time - Pittsfield - Urgently Hiring