Updated November 2026
Best Trucking Companies in Winter Garden, Florida (November 2026)
253 W2 trucking carriers are currently posting jobs in Winter Garden, Florida as of November 2026. Herrington Transportation Inc. leads with an average weekly pay of $2,000. True Transport Inc. follows at $2,250/week. Florida trucking runs on I-95 / I-75 north-south spines and the I-4 Tampa-Orlando-Daytona cross, with Port of Miami and Port of Jacksonville as major gateways alongside heavy citrus and produce agriculture freight.
What changed in November 2026
Mountain States L.P. Gas at #4 and ARKA EXPRESS INC at #8 are new to the top 50 in Winter Garden, Florida. Biggest climbs: DICK LAVY TRUCKING (#30 → #6) and Herrington Transportation Inc. (#22 → #1). Biggest fall: REISCH TRUCKING INC (#29 → #46). H & M TRUCKING INC (was #10) left the top 50. Average weekly pay moved most at DICK LAVY TRUCKING (up 28.5% from $1,517 to $1,950). Elsewhere in the top 50, 2 carriers joined, 3 left, and 40 changed rank.
All changes since October 2026
| Carrier | Last month | This month | Change |
|---|---|---|---|
| Herrington Transportation Inc. | #22 | #1 | Up 21 places |
| True Transport Inc. | #5 | #2 | Up 3 places |
| JK MOVING & STORAGE INC | #1 | #3 | Down 2 places |
| Mountain States L.P. Gas | Not ranked | #4 | New |
| Covenant Transport Inc | #2 | #5 | Down 3 places |
| DICK LAVY TRUCKING | #30 | #6 | Up 24 placesweekly pay up 28.5% ($1,517 → $1,950) |
| PRAIRIE FIELD SERVICES LLC | #4 | #7 | Down 3 places |
| ARKA EXPRESS INC | Not ranked | #8 | New |
| South East Carriers INC | #3 | #9 | Down 6 places |
| G-DIAMOND TRANSPORT INC | #6 | #10 | Down 4 places |
| Diaz Stone & Pallet Inc. | #7 | #11 | Down 4 places |
| ELBERTA LOGISTICS INTERNATIONAL LLC | #8 | #12 | Down 4 places |
| MC CARRIER LLC | #12 | #13 | Down 1 place |
| BRADY TRUCKING INC | #9 | #14 | Down 5 places |
| A & H INC | #21 | #15 | Up 6 places |
| HOLLAND ENTERPRISES INC | #14 | #16 | Down 2 places |
| M&D TRANSPORT | #15 | #17 | Down 2 places |
| NEIER INC | #16 | #18 | Down 2 places |
| G & C FOOD DISTRIBUTORS & BROKERS INC | #17 | #20 | Down 3 places |
| RIVER CITY TRANSPORT INC | #13 | #21 | Down 8 places |
| LUCKY WORLD INC | Not ranked | #22 | New |
| Excel Trucking LLC | #18 | #23 | Down 5 places |
| Creedence Energy Services LLC | #20 | #24 | Down 4 places |
| CARGORX DRY CAPACITY | #26 | #25 | Up 1 place |
| Z TRANSPORTATION INC | #24 | #26 | Down 2 places |
| AN ENTERPRISE INC | #23 | #27 | Down 4 places |
| Brenny Specialized Inc | #25 | #28 | Down 3 places |
| ROWLAND TRUCK LINES INC | #27 | #29 | Down 2 places |
| HUTCHINSON TRUCKING LLC | #28 | #30 | Down 2 places |
| COYOTE XPRESS LLC | Not ranked | #31 | New |
| Cross Integrated Transport, LLC | #33 | #32 | Up 1 place |
| REVV TRANSPORT | #34 | #33 | Up 1 place |
| Caravan Inc | #31 | #34 | Down 3 places |
| CTK LOGISTICS LLC | #32 | #35 | Down 3 places |
| Southland Transportation | #35 | #37 | Down 2 places |
| JL LOGISTICS INC | #37 | #38 | Down 1 place |
| VITAL TRANSPORTATION CORP | #40 | #39 | Up 1 place |
| Idea Transport LLC | #38 | #40 | Down 2 places |
| Bakers Express | #39 | #41 | Down 2 places |
| SEMO EXPRESS LLC | #41 | #43 | Down 2 places |
| S & R TRANSPORTATION LLC | #43 | #44 | Down 1 place |
| EAGLE EYE TRUCK LINES LLC | #44 | #45 | Down 1 place |
| REISCH TRUCKING INC | #29 | #46 | Down 17 places |
| LIBERTY HAULERS INC | #45 | #47 | Down 2 places |
| 1 MTX LLC | #46 | #48 | Down 2 places |
| Parks Motor Group Inc | #47 | #49 | Down 2 places |
| BROADWATER LOGISTICS & TRANSPORTATION INC | #49 | #50 | Down 1 place |
| H & M TRUCKING INC | #10 | Not ranked | Dropped out |
| WILLIAMS PRESTIGE ENTERPRISE | #11 | Not ranked | Dropped out |
| Detmar Logistics | #48 | Not ranked | Dropped out |
| HORIZON TRANSPORTATION | #50 | Not ranked | Dropped out |
Winter Garden, Florida's top trucking carriers right now
The top of the list is Herrington Transportation Inc. at $2,000/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1Herrington Transportation Inc. — $2,000/wk
Herrington Transportation Inc. leads the Winter Garden, Florida market on combined pay and ranking score this month. Weekly pay here lands in the 89th percentile across Winter Garden, Florida. The carrier tracks as a responsive employer on Lanefinder's data.
#2True Transport Inc. — $2,250/wk
True Transport Inc. sits in the 96th percentile for weekly pay among Winter Garden, Florida 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.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC pays above the 89th percentile on weekly pay for the Winter Garden, Florida market. Strongest FMCSA dimension is vehicle maintenance — 94th percentile.
Also in the top 10: #4 Mountain States L.P. Gas at $2,000/wk, #5 Covenant Transport Inc at $1,762/wk, #6 DICK LAVY TRUCKING at $1,950/wk, #7 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #8 ARKA EXPRESS INC at $1,750/wk, #9 South East Carriers INC at $1,600/wk, #10 G-DIAMOND TRANSPORT INC at $2,045/wk.
How drivers spend their time on the road in Winter Garden, Florida
Of active CDL postings in Winter Garden, Florida this month, 18% are regional and 79% are OTR (long-haul). Local and semi-local routes account for the remaining 3%.
Across Winter Garden, Florida CDL postings: 3% with guaranteed pay, 29% dedicated, 81% take-truck-home, 63% pet-friendly, 67% riders-allowed.
Where Winter Garden, Florida differs from the Florida baseline
The largest gap is on dedicated routes: Winter Garden, Florida sits 10 points above the Florida baseline.
Driving CDL in Florida
Florida CDL work splits cleanly between coastal port-and-tourism freight (Miami, Jacksonville, Tampa, Port Everglades) and Central Florida last-mile distribution. The hurricane season — June through November — drives both stress and opportunity: insurance rates climb, freight rates spike around storm-recovery windows, and shutdown days are a real income variable. Florida has no state income tax. Miami-area I-95 is among the more congested US corridors, so HOS planning around peak commute windows matters more here than in most states. Reefer and produce work pays well; OTR pulling out of the state is steady year-round.
Related guides
- Best owner-operator companies in Winter Garden, Florida
- CDL driver salary in Winter Garden, Florida
- Best trucking companies in Florida
The methodology behind the rankings
Pay carriers against each other within the same market (30%). Layer a weighted FMCSA SAFER safety percentile on top (25%). Score the benefits package against what actually matters for the hiring type — W2 health/financial benefits or owner-op operational perks (25%). Finish with operational performance: responsiveness to driver applications plus fleet scale (20%). All percentiles are recomputed monthly. Updated November 2026.