Updated November 2026
Best Trucking Companies in Chesapeake, Virginia (November 2026)
273 W2 trucking carriers are hiring in Chesapeake, Virginia this November 2026. HandledNow LLC leads with an average weekly pay of $1,800 and an average $2,500 sign-on bonus. Herrington Transportation Inc. follows at $2,000/week. Virginia freight is anchored by the Port of Virginia at Norfolk and Hampton Roads, the deepest commercial harbor on the East Coast (55 ft after the Gateway dredging program), with I-95 / I-64 / I-81 truck corridors connecting it to the mid-Atlantic and Southeast markets.
What changed in November 2026
SAFE WAY CARRIER LLC at #5, Mountain States L.P. Gas at #6, and DICK LAVY TRUCKING at #8 are new to the top 50 in Chesapeake, Virginia. Biggest climb: Herrington Transportation Inc. (#28 → #2). Biggest falls: LAWRENCE TRANSPORTATION COMPANY (#2 → #20) and REISCH TRUCKING INC (#37 → #48). Elsewhere in the top 50, 5 carriers joined, 8 left, and 37 changed rank.
All changes since October 2026
Where CDL pay is strongest in Chesapeake, Virginia this month
The top of the list is HandledNow LLC at $1,800/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1HandledNow LLC — $1,800/wk
HandledNow LLC tops the Chesapeake, Virginia ranking with the strongest composite score across pay, safety, benefits, and operational signals. Strongest FMCSA dimension is driver fitness — 99th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#2Herrington Transportation Inc. — $2,000/wk
Herrington Transportation Inc. is up from #28 last month, one of the largest jumps in the Chesapeake, Virginia ranking. Weekly pay here lands in the 88th percentile across Chesapeake, Virginia. Herrington Transportation Inc. tracks as a responsive employer on application-response data.
#3True Transport Inc. — $2,250/wk
True Transport Inc. sits in the 95th percentile for weekly pay among Chesapeake, Virginia carriers. True Transport Inc.'s FMCSA score is strongest on unsafe-driving avoidance — 98th percentile.
True Transport Inc. doesn't top the ranking but offers higher weekly pay than #1 — $2,250/week.
Also in the top 10: #4 JK MOVING & STORAGE INC at $2,200/wk, #5 SAFE WAY CARRIER LLC at $2,100/wk, #6 Mountain States L.P. Gas at $2,000/wk, #7 Covenant Transport Inc at $1,762/wk, #8 DICK LAVY TRUCKING at $1,950/wk, #9 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #10 JS HELWIG & SON LLC at $1,850/wk.
What Chesapeake, Virginia drivers actually run
Of active CDL postings in Chesapeake, Virginia this month, 19% are regional and 78% are OTR (long-haul). Local and semi-local routes account for the remaining 3%.
Across Chesapeake, Virginia CDL postings: 2% with guaranteed pay, 26% dedicated, 82% take-truck-home, 69% pet-friendly, 67% riders-allowed.
Chesapeake, Virginia vs Virginia: the numbers that diverge
| Chesapeake, Virginia | Virginia top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 40% | 46% | -6 pt |
| Dedicated routes | 24% | 40% | -16 pt |
| Pet-friendly fleets | 76% | 66% | +10 pt |
| Riders-allowed policies | 84% | 78% | +6 pt |
Source: Lanefinder index, November 2026
The largest gap is on dedicated routes: Chesapeake, Virginia sits 16 points below the Virginia baseline.
Driving CDL in Virginia
Virginia freight is anchored by the Port of Virginia at Norfolk and Hampton Roads — the deepest commercial harbor on the East Coast and a top-tier US container gateway. The I-95 / I-64 / I-81 truck corridors connect Norfolk to mid-Atlantic and Southeast markets, with I-81 north-south through the Shenandoah Valley a major regional freight spine. Cost of living varies widely (high in Northern Virginia, moderate elsewhere). Virginia has a moderate graduated state income tax. Northern Virginia (DC suburbs) congestion is consistently top-tier; central and western VA is generally easier driving.
Related guides
- Best owner-operator companies in Chesapeake, Virginia
- CDL driver salary in Chesapeake, Virginia
- Best trucking companies in Virginia
The methodology behind the rankings
Compensation, FMCSA safety, benefits, and operational performance — weighted 30, 25, 25, and 20 percent respectively. Compensation extends beyond headline pay to include sign-on bonus tier and settlement cadence. Benefits scoring differs by hiring type because the perks that matter to a W2 driver and a contractor are not the same. Updated November 2026.