Eagle Systems · Boston terminal

Local Owner Operator Jobs in Boston, MA

Eagle Systems hires CDL-A owner operators for import and export container drayage around Boston, pulling from Conley Container Terminal in South Boston and the CSX ramp in Worcester. You gross $3,000–$5,000 a week, get home daily and pick your loads. Conley's inbound gate closes at 4:15 p.m., or 3:15 p.m. on Fridays.

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Weekly gross: $3,000–$5,000
Home time: Daily
Dispatch: Not forced
Open now: 1 job

Gross revenue before fuel, insurance and truck expenses. Not a guarantee; actual earnings vary by loads, lane and costs.

Freight from this terminal

Conley Terminal boxes and Worcester double-stacks

Your freight comes from Conley, which Massport calls the only full-service container terminal in New England, and from CSX's Worcester rail terminal. If drayage is new to you, start with an explainer on intermodal drayage.

Ports served

Conley Container Terminal

Rail ramps served

CSX Worcester

Freight handled

20', 40', 45' international containers
Open tops
Flat racks
Wine & spirits
Residential deliveries
Bonded carrier

Local know-how

Running Conley Terminal in South Boston

Massport owns and runs Conley at 700 Summer Street in South Boston. Gates open 8 a.m. to 5 p.m. on weekdays, but the inbound gate closes at 4:15 p.m., or 3:15 p.m. on Fridays. You need an active, time-stamped Yard Pass before that cutoff.

Getting in takes a TWIC, Massport Maritime Credentials issued against that TWIC, a Massport trucker code and a safety vest, since the rule is no vest, no entry. Loads pre-gate in Scale Lanes 1–3, then go to inspection. You check container availability in Tideworks Forecast or its mobile app.

Leaving the terminal, you take the Thomas J. Butler Freight Corridor, a dedicated truck route that keeps container traffic off residential streets. Rail boxes come from CSX Worcester at 165 Grafton Street, where 31 raised bridges gave New England its first double-stack-cleared line to the New York border.

Sources (7)

Home time and schedule

A day built around Conley's gate cutoff

A day can start with an import box at Conley Terminal, a delivery out of the city by way of the Butler Freight Corridor, and an empty back before the 4:15 p.m. inbound cutoff.

01
Start near home
Roll out from home or the Boston yard.
02
Pick up the box
Conley Container Terminal
03
Deliver local
Customers around Boston.
04
Return the empty
Back to the port, ramp or yard.
05
Home tonight
Every night. No forced dispatch.

Pay and settlements

Weekly gross for Boston owner operators

Eagle owner operators gross $3,000–$5,000 a week across the company and get settled weekly by direct deposit. Read the guide to owner operator pay and settlements first.

Weekly direct depositSettlements land in your account every week.
Nationwide fuel discountsFuel card with discounts across the network.
Low-cost insuranceLow-cost insurance premiums for leased-on operators.
Clean inspection bonusesPaid for clean roadside inspections.
Flexible schedulingBuild the week around your business.

Weekly gross revenue

$3,000–$5,000

per week, before truck costs

$1k

$2k

$3k

$4k

$5k

$6k

Paid: Weekly, by direct deposit
Fuel: Nationwide fuel card discounts
Bonus: Clean roadside inspections

Gross revenue before fuel, insurance and truck expenses. Not a guarantee; actual earnings vary by loads, lane and costs.

Hiring area

Hiring around Boston

The live list and map below show today's owner operator jobs in Boston, MA; a recruiter confirms whether your ZIP is in the hiring area. Outside New England, look at owner operator jobs in Kearny, NJ, Elizabeth, NJ pier work and, farther west, Syracuse, NY rail drayage. You can also browse all owner operator jobs in Massachusetts.

Boston, MAlocal

Live openings

1 open position near Boston

Each opening has its own job page with the full description.

Openings updated October 30, 2026

Owner operator job in Boston, MA · posting #14025 · CDL A Owner Operator Local Intermodal Truck Drivernear the Boston terminal

Equipment and requirements

What you need to lease on

Read the owner operator requirements before you apply. Conley also requires a TWIC and Massport Maritime Credentials.

01Valid Class A CDLCurrent CDL-A in good standing.
02Tractor-trailer experience2 years verifiable, or 1 year plus a certified trucking school certificate.
03Your own truckYou own a commercial motor vehicle.
042000 or newer, or ELD compliantTruck model year 2000+ or ELD compliant.
0521 or olderAsked on the Quick App.
06Safety standardsMeet Eagle's safety and qualification standards.

Support

What Eagle Systems sets you up with

Fuel card with nationwide discounts
Plate and registration program
IFTA fuel tax program
Easy-to-install ELD
Front-facing dash cameras
Mobile dispatching app

Local FAQ

Boston owner operator questions

Which port and rail ramp do Boston owner operators run?

Conley Container Terminal in South Boston, owned and operated by Massport, and the CSX intermodal terminal on Grafton Street in Worcester. Conley is the port work; Worcester, in central Massachusetts, is the rail ramp work.

Are there owner operator openings near Boston right now?

Yes. 1 posting is live within about 160 miles of the Boston terminal as of October 30, 2026: Boston. Distances are straight-line miles; a recruiter confirms which yard you would run from and the hiring area for your ZIP code.

Do I need a TWIC for Conley Terminal?

Yes, for unescorted access. You also need Massport Maritime Credentials, which you get by showing your TWIC, and a vest, because Conley runs a no vest, no entry rule. Truckers also need a Massport-assigned trucker code.

What are the Conley Terminal gate hours?

Monday through Friday, 8:00 a.m. to 5:00 p.m. The inbound gate closes at 4:15 p.m., and at 3:15 p.m. on Fridays. Your Yard Pass must be active and time-stamped by the cutoff.

What moves through CSX Worcester?

Double-stack intermodal containers. CSX expanded the Worcester terminal and raised 31 bridges to 21 feet, clearing New England's first double-stack route to the New York border and linking it to double-stack routes across the country.

How much do Boston owner operators gross with Eagle?

Leased-on owner operators gross $3,000–$5,000 a week company-wide, paid weekly by direct deposit. That figure is gross, before fuel, insurance and upkeep on your truck.

What comes with leasing on?

A fuel card with nationwide discounts, plate and registration and IFTA programs, an ELD, front-facing dash cameras and a mobile dispatching app. See what Eagle includes for leased-on operators.