CITY DIRECTORY · MARYLAND

Trucking companies in Chestertown, MD

136 FMCSA-registered trucking companies are based in Chestertown. The typical fleet runs 1 power unit, and most haul general freight. Chestertown's vehicle out-of-service rate sits at 13.4%, below the 22.26% national average.

136
Registered companies
15
Active for-hire authorities
1
Median fleet (power units)
13.4%
Vehicle OOS · nat’l 22.26%
2
New registrations, 30 days

Showing 1–25 of 136 companies

Neff and Son IncClear · 100
DBA Chester River Landscaping & Clovelly Nurseries
USDOT 791669 · MC-1395548 · Chestertown
General FreightBuilding MaterialsMachinery, Large Objects+6
105
Power units
10.2%
Vehicle OOS
27 yr
Registered
David A Bramble IncReview · 90
USDOT 127533 · MC-803004 · Chestertown
Building MaterialsMachinery, Large ObjectsLiquids/Gases+4
85
Power units
3.9%
Vehicle OOS
52 yr
Registered
Talkie Communications IncReview · 79
DBA Talkie
USDOT 3325627 · Chestertown
General FreightMachinery, Large ObjectsUtilities+1
35
Power units
23.7%
Vehicle OOS
7 yr
Registered
Gillespie & Son IncClear · 100
USDOT 131237 · Chestertown
Building MaterialsCommodities Dry BulkConstruction+1
34
Power units
17.1%
Vehicle OOS
52 yr
Registered
Alger Oil IncReview · 82
DBA Alger Oil & Propane
USDOT 33679 · MC-919376 · Chestertown
Liquids/GasesOther
21
Power units
0.0%
Vehicle OOS
52 yr
Registered
Eastern Shore Events LLCReview · 84
DBA Eastern Shore Tents and Events
USDOT 3380454 · Chestertown
General FreightOther
18
Power units
31.6%
Vehicle OOS
6 yr
Registered
Dixon Valve & Coupling CoClear · 85
USDOT 151029 · MC-215272 · Chestertown
General FreightMachinery, Large Objects
12
Power units
12.5%
Vehicle OOS
52 yr
Registered
Stoltzfus Brothers Shore Construction LLCClear · 100
USDOT 2299265 · Chestertown
General FreightMetal: Sheets, Coils, RollsLogs, Poles, Beams, Lumber+6
11
Power units
—
Vehicle OOS
14 yr
Registered
Prince Limousine IncClear · 95
USDOT 899027 · MC-1422753 · Chestertown
Passengers
10
Power units
4.2%
Vehicle OOS
26 yr
Registered
MGN Transport LLCClear · 87
USDOT 4319337 · MC-1684961 · Chestertown
General FreightBuilding MaterialsGrain, Feed, Hay+4
10
Power units
23.3%
Vehicle OOS
2 yr
Registered
Sharp Lawn & Tree IncClear · 100
USDOT 936229 · Chestertown
Machinery, Large ObjectsOther
9
Power units
—
Vehicle OOS
25 yr
Registered
W A Clark Jr & Son IncClear · 100
USDOT 836318 · Chestertown
MeatRefrigerated FoodOther
7
Power units
—
Vehicle OOS
27 yr
Registered
Bennett and Cohey Auto Salvage IncReview · 84
USDOT 469102 · MC-955114 · Chestertown
General FreightBuilding MaterialsMachinery, Large Objects+5
6
Power units
40.0%
Vehicle OOS
34 yr
Registered
Anthonys Flowers and Landscaping IncClear · 100
USDOT 1226064 · Chestertown
Logs, Poles, Beams, LumberBuilding MaterialsMachinery, Large Objects+4
6
Power units
—
Vehicle OOS
22 yr
Registered
Sunrise Solar IncReview · 87
USDOT 2514878 · Chestertown
General FreightMetal: Sheets, Coils, RollsLogs, Poles, Beams, Lumber+2
6
Power units
0.0%
Vehicle OOS
12 yr
Registered
Happy Grass Lawn CareClear · 95
USDOT 2387338 · Chestertown
Machinery, Large ObjectsOther
5
Power units
—
Vehicle OOS
13 yr
Registered
Perfection Transport LLCReview · 84
USDOT 2981092 · MC-17692 · Chestertown
General FreightHousehold GoodsFresh Produce+5
5
Power units
33.3%
Vehicle OOS
9 yr
Registered
Pardoe's Lawn & Tree Service IncClear · 100
USDOT 480573 · Chestertown
Other
4
Power units
—
Vehicle OOS
34 yr
Registered
Lowman Construction IncClear · 95
USDOT 1174697 · Chestertown
Building MaterialsMachinery, Large ObjectsGarbage/Refuse+1
4
Power units
—
Vehicle OOS
23 yr
Registered
Chestertown Lumber Co LLCClear · 100
USDOT 1243208 · Chestertown
Logs, Poles, Beams, LumberBuilding MaterialsConstruction
4
Power units
—
Vehicle OOS
22 yr
Registered
JBK Hardware IncClear · 100
DBA JBK Ace Hardware
USDOT 1283084 · Chestertown
General FreightHousehold GoodsMachinery, Large Objects
4
Power units
—
Vehicle OOS
22 yr
Registered
Chesapeake Boat Lift Services LLCClear · 95
USDOT 2288811 · Chestertown
General FreightMetal: Sheets, Coils, RollsLogs, Poles, Beams, Lumber+1
4
Power units
—
Vehicle OOS
14 yr
Registered
Raymond Harrison Septic Service LLCClear · 100
USDOT 3043665 · Chestertown
Building MaterialsMachinery, Large ObjectsLiquids/Gases+2
4
Power units
—
Vehicle OOS
9 yr
Registered
Charles DebnamClear · 95
DBA Pond View Farm
USDOT 3368796 · Chestertown
Grain, Feed, HayAgricultural/Farm SuppliesOther
4
Power units
—
Vehicle OOS
6 yr
Registered
Dependable Pest Management LLCReview · 80
USDOT 4579019 · Chestertown
Metal: Sheets, Coils, RollsLogs, Poles, Beams, LumberBuilding Materials+4
4
Power units
—
Vehicle OOS
<1 yr
Registered

Chestertown trucking FAQ

How many trucking companies are in Chestertown?

136 active motor carriers and freight brokers list a Chestertown physical address in the FMCSA census, of which 15 hold active operating authority.

Which Chestertown trucking companies have the largest fleets?

The directory is ranked by power units reported on each company's latest MCS-150 filing. Use the "Largest fleets" view to see companies running 50 or more trucks.

How do I check if a Chestertown carrier is safe to load?

Open any profile for its operating authority status, insurance on file, 24-month out-of-service rates against the national average, crash history and identity checks, summarized as a load-decision score.

What is the out-of-service rate for Chestertown carriers?

Over the last 24 months, 13.4% of vehicle inspections on Chestertown-based carriers resulted in an out-of-service order, compared with 22.26% nationally.