OTR Oversized Driver Jobs in Massachusetts — Now Hiring

What does an oversized driver actually haul?

This over-the-road oversized seat is domiciled in Boston, Massachusetts. The work is the state's freight, not a generic oversized explainer — the lanes out of Boston set the loads.

Full oversized driver guide — top carriers, endorsements and career path

Where in Massachusetts would you actually be running?

Freight here moves on a handful of named lanes. These are the ones an oversized seat domiciled in Boston is most likely to see.

• Boston: I-93, I-90, I-95 — Healthcare & Biotech and Higher Education freight.
• Worcester: I-90, I-290, I-190 — Distribution & Logistics and Healthcare freight.
• Springfield: I-91, I-90, I-291 — Healthcare and Manufacturing freight.

What does this oversized seat pay in Massachusetts?

The band on this posting is $73,500 - $104,000/year. Where you land inside it comes down to verifiable experience, the lane you take, and your safety record.

For context, the statewide CDL-A average is $63,570. Wages here are stable — Massachusetts trucking wages are high but offset by the steep cost of living. The Port of Boston, healthcare logistics, and dense last-mile delivery needs support steady demand.

Massachusetts runs a cost-of-living index of 131, so this band is worth roughly $48,527 once living costs are taken out. That number is what to compare against an offer in another state.

• Strongest-paying metros in Massachusetts:
• Boston — about $71,198
• Worcester — about $66,113
• Springfield — about $66,113

Massachusetts CDL pay breakdown by experience level and equipment

What do you need to qualify?

• CDL-A and 1+ years of verifiable driving time.
• Domiciled in or around Boston, MA — that is the reset market, not a yard you clock into.

Full oversized requirements and endorsements

What is the hardest part of this job?

We would rather you know now than quit in week three. The one that catches people on this seat: extremely high responsibility — a mistake with a 200,000-pound load on a 19-axle trailer can be catastrophic

Pros, cons and a day in the life of an oversized driver

What should an oversized driver know before running Massachusetts?

Oversize work in Massachusetts starts where the legal limits stop: 80,000 lbs (99,000 lbs on Massachusetts Turnpike with permit) gross, 22,400 lbs single axle, 36,000 lbs tandem. Anything past that is a permit load, and permits go through MassDOT Highway Division. Very strict routing in Boston metro. Many low bridges and narrow roads restrict oversize loads.

Fuel tax in Massachusetts is $0.24 per gallon diesel + federal, which matters if you are comparing per-mile offers across state lines. Inspection climate: Moderate. Massachusetts State Police conduct targeted enforcement. Focus on Boston metro area, I-90, and I-95 corridors.

Which Massachusetts rules catch oversized drivers out?

• Gross weight limit: 80,000 lbs (99,000 lbs on Massachusetts Turnpike with permit)
• Axle weight: 22,400 lbs single axle, 36,000 lbs tandem
• Truck speed limits: 65 mph rural, 55 mph urban
• Diesel fuel tax: $0.24 per gallon diesel + federal
• Tolls: Massachusetts Turnpike (I-90 full length), Tobin Bridge, Sumner/Callahan/Ted Williams tunnels (Boston). All-electronic tolling via E-ZPass or license plate. Truck tolls $4-20+ depending on distance.
• Inspection posture: Moderate. Massachusetts State Police conduct targeted enforcement. Focus on Boston metro area, I-90, and I-95 corridors.
• Storrow Drive and Memorial Drive in Boston prohibit ALL trucks (frequent bridge strikes by GPS-ignoring drivers)
• Many low bridges throughout greater Boston area
• Massachusetts Turnpike is all-electronic tolling (no cash)

All Massachusetts driving jobs and state regulations

How does applying through us work?

1. 1You send the short form on this page. It takes under a minute and needs no resume.
2. 2A recruiter reads it and calls you — a real person, not an automated screen.
3. 3We match you against the over-the-road oversized openings our client carriers have right now, including ones never posted publicly.
4. 4You choose which to interview for. Nothing is submitted anywhere without you saying yes.
5. 5There is no cost to you at any point. Carriers pay us, drivers never do.

Are these jobs actually live?

Yes — and it is a fair thing to ask, because plenty of driver postings are not.

Ahmad Qazi, sales representative at TruckingJobsInUSA: “Carriers have filled seats through this platform, and the owners we place drivers with are straightforward to deal with. If a seat is gone, we take the posting down rather than leave it up to collect applications.”

Every posting on this site is republished on the date shown, so what you are reading is current recruitment, not an archive.