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Eagle Systems · Winchester terminal

Local Owner Operator Jobs in Winchester, VA

Eagle Systems hires CDL-A owner operators for import and export container drayage from its terminal at 1748 Berryville Pike in Winchester. Most boxes move through the Virginia Inland Port in Front Royal, about 20 miles south. You gross $3,000–$5,000 a week and get home daily. The inland port's truck gate runs 7:00 AM to 4:00 PM on weekdays.

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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

Front Royal rail and the Hampton Roads terminals

Your main stop is the Virginia Inland Port, a Norfolk Southern rail terminal that shuttles containers about 220 miles to and from the Port of Virginia's NIT and VIG terminals. New to port freight? Read what intermodal drayage is.

Ports served

  • Norfolk International Terminals (NIT)
  • Virginia International Gateway (VIG)

Rail ramps served

  • Virginia Inland Port (Front Royal, NS)

Freight handled

  • 20', 40', 45' international containers
  • Bonded carrier

Local know-how

Hauling the Virginia Inland Port from Winchester

The Virginia Inland Port sits at 7685 Winchester Road in Front Royal, on I-66 about 7 miles from I-81. Its truck gate runs 7:00 AM to 4:00 PM on weekdays, with a drop lot for weekend service. It is a US Customs port of entry with 24 reefer plugs and port-provided chassis on the terminal.

Much of the freight stays close. Family Dollar, Home Depot, Sysco, Ferguson, Red Bull and UPS all run distribution sites in Front Royal and Warren County near the inland port. I-66 also puts Northern Virginia and I-95 within about an hour.

A run to the coast is about 230 miles each way. NIT and VIG require a TWIC, Port of Virginia registration, a PRO-PASS RFID tag tied to your plate and a PRO-PASS reservation during mandatory hours. Closer to home, VDOT is adding a third I-81 lane near exit 317 and rebuilding the bridges over Route 11.

Sources (10)
  1. Virginia Inland Port one-pager — Port of Virginia
  2. Terminal gate hours — Port of Virginia
  3. New motor carrier setup — Port of Virginia
  4. PRO-PASS FAQ
  5. Logistics — Front Royal-Warren County EDA
  6. I-81 MM 317.0–318.8 widening and exit 317 improvements — VDOT
  7. Our capabilities — Port of Virginia
  8. Virginia Inland Port — Virginia Places
  9. Va. Code § 46.2-1141 — Virginia LIS
  10. Hauling permits — Virginia DMV

Home time and schedule

From the Front Royal gate to Warren County docks

Most days start at the Virginia Inland Port gate when it opens at 7:00 AM, with a delivery to a DC in Front Royal or out I-81 and I-66, and the empty back before the 4:00 PM close.

  1. 01

    Start near home

    Roll out from home or the Winchester yard.

  2. 02

    Pick up the box

    Norfolk International Terminals (NIT)

  3. 03

    Deliver local

    Customers around Winchester.

  4. 04

    Return the empty

    Back to the port, ramp or yard.

  5. 05

    Home tonight

    Every night. No forced dispatch.

Pay and settlements

What Winchester owner operators gross

You gross $3,000–$5,000 a week, the same range across Eagle, paid weekly by direct deposit. Learn how owner operator pay and weekly settlements work before your first call.

  • 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

$0
$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

Who runs out of Berryville Pike

Owner operator jobs in Winchester, VA update in the live list and map below, and your recruiter confirms the hiring area for your ZIP. If you live closer to Pennsylvania or Maryland, compare owner operator jobs in Harrisburg, PA or Baltimore, MD, and on the coast there are owner operator jobs in Norfolk, VA. See every owner operator job in VA.

Eagle Systems Winchester terminalBaltimoreHarrisburg
  • Winchester, VAlocal

Live openings

1 open position near Winchester

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

Openings updated

Equipment and requirements

What you need to lease on

Check the owner operator requirements before you apply. For runs to NIT or VIG you also need a TWIC and a PRO-PASS tag on your truck.

  • 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

Winchester owner operator questions

Where do Winchester drivers pick up containers?

Mostly at the Virginia Inland Port at 7685 Winchester Road in Front Royal, about 20 miles from Eagle's yard. Norfolk Southern runs a rail shuttle from there to the Port of Virginia terminals in Hampton Roads, so imports reach the valley without a coast run.

Are there owner operator openings near Winchester right now?

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

What are the Virginia Inland Port gate hours?

The truck gate runs Monday through Friday, 7:00 AM to 4:00 PM, and LTL runs 7:00 AM to 3:30 PM. A drop lot covers weekend service. Those hours are shorter than the coast terminals, so start early.

Do I need a TWIC for runs to the coast terminals?

For runs to NIT or VIG, yes. The Port of Virginia also requires motor carrier registration, a PRO-PASS RFID tag tied to the plate, and a PRO-PASS reservation during mandatory hours. Trucks without a reservation in those hours are turned away.

Can I haul an overweight sealed container in Virginia?

Virginia Code § 46.2-1141 lets DMV issue overweight permits for sealed seagoing containers moving to or from a seaport with contents unchanged, through the DMV Hauling Permit Office. The statute does not mention inland ports, so check before routing a heavy box through Front Royal.

How much do owner operators make hauling out of Winchester?

Eagle owner operators gross $3,000–$5,000 a week. The range is company-wide, not a Winchester figure, and it is gross revenue before your fuel and truck expenses.

What comes with leasing on at the Winchester terminal?

A fuel card with nationwide discounts, plate and registration and IFTA programs, low-cost insurance, an ELD, dash cameras and a mobile dispatching app. The details are in what leasing on with Eagle includes.

Apply

Run Front Royal and be home tonight

Send the Quick App and the Winchester terminal will call about openings, port credentials and your truck.

  1. Send the Quick App

    A short form: contact details and a few yes/no questions.

  2. Talk to a recruiter

    Pay, freight and your truck, for the terminal near you.

  3. Lease on and run

    Plates, IFTA, ELD and fuel card set up with you.

Quick AppAbout a minute. A recruiter calls you back.Full applicationComplete DOT application, start to finish.

Both open Eagle Systems' secure application on IntelliApp.

Prefer to talk? 540-667-6746

Nearby terminals

Close to Winchester

All Virginia owner operator jobs →

Baltimore, MD

Dundalk, MD

: Waitlist

Seagirt Marine Terminal · CSX Intermodal Container Transfer Facility (Seagirt) rail ramp

88 mi away

Harrisburg, PA

Enola, PA

: 3 open

NS Harrisburg rail ramp · NS Rutherford rail ramp · NS Greencastle rail ramp · CSX Chambersburg rail ramp

100 mi away

Norfolk, VA

Chesapeake, VA

: 6 open

Norfolk International Terminals (NIT) · Virginia International Gateway (VIG) · On-dock rail at NIT and VIG (NS and CSX) rail ramp

193 mi away

Questions about Winchester? Call the terminal at 540-667-6746.

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