Trucking Companies in CHESTERTOWN, Maryland

What FMCSA data shows for CHESTERTOWN, Maryland

Active motor carriers headquartered here

131

Reported power units

557 across the 130 of 131 carriers that reported fleet data

Reported drivers

606 across the 131 of 131 carriers that reported driver counts

Reported fleet size

• 1–5 power units 116
• 6–24 10
• 25–99 4
• 100 or more 0
• Reported zero 0
• Not reported 1

Largest carriers by reported power units

The 25 carriers headquartered in CHESTERTOWN, Maryland with the most power units reported to FMCSA. Fleet size is not a ranking of pay, safety, or hiring.

• CHESTER RIVER LANDSCAPING & CLOVELLY NURSERIES

  • USDOT 791669
  • CHESTERTOWN
  • Power units 94
  • Drivers 87

• DAVID A BRAMBLE INC

  • USDOT 127533
  • CHESTERTOWN
  • Power units 85
  • Drivers 128

• TALKIE

  • USDOT 3325627
  • CHESTERTOWN
  • Power units 35
  • Drivers 30

• GILLESPIE & SON INC

  • USDOT 131237
  • CHESTERTOWN
  • Power units 34
  • Drivers 18

• ALGER OIL & PROPANE

  • USDOT 33679
  • CHESTERTOWN
  • Power units 21
  • Drivers 9

• EASTERN SHORE TENTS AND EVENTS

  • USDOT 3380454
  • CHESTERTOWN
  • Power units 18
  • Drivers 12

• DIXON VALVE & COUPLING CO

  • USDOT 151029
  • CHESTERTOWN
  • Power units 12
  • Drivers 23

• STOLTZFUS BROTHERS SHORE CONSTRUCTION LLC

  • USDOT 2299265
  • CHESTERTOWN
  • Power units 11
  • Drivers 14

• PRINCE LIMOUSINE INC

  • USDOT 899027
  • CHESTERTOWN
  • Power units 10
  • Drivers 10

• MGN TRANSPORT LLC

  • USDOT 4319337
  • CHESTERTOWN
  • Power units 10
  • Drivers 10

• W A CLARK JR & SON INC

  • USDOT 836318
  • CHESTERTOWN
  • Power units 7
  • Drivers 2

• BENNETT & COHEY AUTO SALVAGE INC

  • USDOT 469102
  • CHESTERTOWN
  • Power units 6
  • Drivers 6

• ANTHONYS FLOWERS AND LANDSCAPING INC

  • USDOT 1226064
  • CHESTERTOWN
  • Power units 6
  • Drivers 4

• SUNRISE SOLAR INC

  • USDOT 2514878
  • CHESTERTOWN
  • Power units 6
  • Drivers 6

• SHARP LAWN & TREE INC

  • USDOT 936229
  • CHESTERTOWN
  • Power units 5
  • Drivers 4

• HAPPY GRASS LAWN CARE

  • USDOT 2387338
  • CHESTERTOWN
  • Power units 5
  • Drivers 3

• PERFECTION TRANSPORT LLC

  • USDOT 2981092
  • CHESTERTOWN
  • Power units 5
  • Drivers 5

• PARDOE'S LAWN & TREE SERVICE INC

  • USDOT 480573
  • CHESTERTOWN
  • Power units 4
  • Drivers 4

• LOWMAN CONSTRUCTION INC

  • USDOT 1174697
  • CHESTERTOWN
  • Power units 4
  • Drivers 3

• CHESTERTOWN LUMBER CO LLC

  • USDOT 1243208
  • CHESTERTOWN
  • Power units 4
  • Drivers 4

• JBK ACE HARDWARE

  • USDOT 1283084
  • CHESTERTOWN
  • Power units 4
  • Drivers 4

• CHESAPEAKE BOAT LIFT SERVICES LLC

  • USDOT 2288811
  • CHESTERTOWN
  • Power units 4
  • Drivers 6

• RAYMOND HARRISON SEPTIC SERVICE LLC

  • USDOT 3043665
  • CHESTERTOWN
  • Power units 4
  • Drivers 5

• POND VIEW FARM

  • USDOT 3368796
  • CHESTERTOWN
  • Power units 4
  • Drivers 1

• DEPENDABLE PEST MANAGEMENT LLC

  • USDOT 4579019
  • CHESTERTOWN
  • Power units 4
  • Drivers 4

More in Maryland

All trucking companies in Maryland

• BALTIMORE (3,989)
• SILVER SPRING (1,382)
• FREDERICK (1,057)
• GAITHERSBURG (900)
• LAUREL (843)
• HYATTSVILLE (836)
• GLEN BURNIE (794)
• HAGERSTOWN (724)
• UPPER MARLBORO (667)
• ROCKVILLE (645)
• WALDORF (637)
• WESTMINSTER (567)
• BOWIE (560)
• ANNAPOLIS (549)
• PASADENA (542)
• BELTSVILLE (495)
• SALISBURY (491)
• LANHAM (445)
• CLINTON (429)
• COLUMBIA (425)

About this page

Company locations are based on principal physical addresses reported to FMCSA. They do not necessarily represent hiring areas, service areas, terminal locations, or current job availability.

Source: Federal Motor Carrier Safety Administration (FMCSA) Company Census data. FMCSA data as of: August 15, 2026. FMCSA registration data may change over time. This site is not affiliated with or endorsed by FMCSA.