OTR Oversized Driver Jobs in Massachusetts — Now Hiring

TruckingJobsInUSA is actively hiring experienced Oversized drivers for over-the-road (OTR) positions based in Massachusetts. We are a CDL driver recruiting agency placing qualified drivers with vetted, well-established carriers across the United States — and we have immediate openings for drivers domiciled in and around Boston, Massachusetts.

This is a full-time Oversized driving position paying $75,000 - $106,000/year depending on experience, lane, and safety record. Home time: Out 2–3 weeks. We work with multiple client carriers, so once you apply our recruiters match you to the opening that best fits your home-time, pay, and equipment preferences — there is no cost to you, ever.

Pay context for Massachusetts: the statewide CDL-A average is $64,800, and the strongest-paying metros are Boston (about $70,200), Worcester (about $62,800), Springfield (about $60,400). Massachusetts runs above the national cost-of-living average (index 131), so the headline number buys less than it does in a cheaper state — adjusted for living costs it works out closer to $49,466. Wage trend is currently 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.

Running flatbed in Massachusetts means working inside a 80,000 lbs (99,000 lbs on Massachusetts Turnpike with permit) gross limit with 22,400 lbs single axle, 36,000 lbs tandem. Oversize and overweight loads 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.

How it works: apply with the quick form below (under 60 seconds, no resume needed), one of our recruiters calls you to confirm your experience and what you're looking for, and we set up interviews with the carriers that match. You choose the offer that's right for you.

We require a minimum of 12 months of verifiable CDL-A driving experience for this role. If you have at least one year behind the wheel and a clean record, we want to talk to you.