Ken Winning Transportation LLC
2
Power Units
1
Drivers
Est. 2016 (9 yrs)
Authority Age
Not Rated
Safety Rating
Company Overview
KEN WINNING TRANSPORTATION LLC is an active carrier & broker registered with the FMCSA since April 2016. Based in FAIR HAVEN, VT, They are classified as Interstate and operate interstate (beyond 100 miles). Their inferred equipment specializations include Flatbed, Dump Truck, Hopper / Grain, Livestock, Power Only and Hotshot.
Equipment Analysis
Based on FMCSA cargo authorization flags and fleet composition data, Ken Winning Transportation LLC appears to operate the following equipment types:
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Fleet Breakdown
| Equipment | Owned | Term Leased | Trip Leased | Total |
|---|---|---|---|---|
| Trucks | 1 | 0 | 0 | 1 |
| Tractors | 1 | 0 | 0 | 1 |
Fleet Size Classification: 2 Trucks
Authorized Cargo Types
Ken Winning Transportation LLC is authorized to transport the following 9 cargo types:
Operations Scope
CDL Drivers: 1
MCS-150 Mileage: 75,124 miles (2025)
Driver Information
1
Total Drivers
1
CDL Drivers
1
Interstate Drivers
Dispatch Services in VT
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Verify on Official Sources
Cross-reference this carrier's data with official FMCSA systems:
Safety Performance
Good
Below national average OOS rates
O Trucking Safety Grade
2
Inspections
24 months
2
Violations
Total found
0
Out of Service
Orders issued
Out-of-Service Rates vs National Average
✓ Better than national average (-7.0%)
✓ Better than national average (-21.5%)
| Date | State | Level | Violations | OOS |
|---|---|---|---|---|
| 03/10/2026 | MA | Driver Only | 1 | ✓ |
| 07/09/2025 | VT | Walk-Around | 1 | ✓ |
Inspection data from FMCSA (24-month window). Updated daily. View full inspection history on FMCSA →
Violation Breakdown
Insurance & Bonding
BIPD
$1 Million
GREAT WEST CASUALTY CO.
Cargo
Not on file
Bond
Not on file
| Type | Insurance Company | Form | Policy # | Coverage | Effective |
|---|---|---|---|---|---|
| BIPD | GREAT WEST CASUALTY CO. | 91X | GRT02715A | $1 Million | 06/03/2023 |
View Insurance History (4 past records)
| Type | Company | Policy # | Effective | Cancelled | Method |
|---|---|---|---|---|---|
| ZURICH AMERICAN INSURANCE COMPANY | PRA0085123 | 06/03/2016 | 07/04/2018 | TERM/CANCL | |
| SENTRY SELECT INSURANCE COMPANY | A0103207001 | 06/03/2021 | 06/03/2023 | TERM/REPL | |
| NORTHLAND INSURANCE COMPANY | WN241675 | 06/03/2018 | 06/03/2021 | TERM/REPL | |
| ZURICH AMERICAN INSURANCE COMPANY | PRA0085123 | 06/03/2016 | 06/03/2018 | TERM/REPL |
Insurance data sourced from FMCSA. Updated daily. Verify on FMCSA →
Recent Changes
Changes tracked daily from FMCSA data.
Frequently Asked Questions
What equipment does KEN WINNING TRANSPORTATION LLC operate?
Based on their FMCSA cargo classifications and fleet data, KEN WINNING TRANSPORTATION LLC is inferred to operate: Flatbed, Dump Truck, Hopper / Grain, Livestock, Power Only and Hotshot.
Is KEN WINNING TRANSPORTATION LLC's authority currently active?
KEN WINNING TRANSPORTATION LLC currently holds active operating authority with the FMCSA.
How long has KEN WINNING TRANSPORTATION LLC been in business?
KEN WINNING TRANSPORTATION LLC has been registered with the FMCSA since April 2016, making their authority approximately 9 years, 11 months old.
Where is KEN WINNING TRANSPORTATION LLC located?
KEN WINNING TRANSPORTATION LLC is physically located at 8 MECHANIC ST, FAIR HAVEN, VT 05743.
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