10 Best Trucking Companies To Work for in Chesapeake, VA
We reviewed key factors — including pay, benefits, training, and work-life balance — across 115 trucking companies in Chesapeake, VA. Our analysis shows that Sysco Hampton Roads, Inc. stands out as the best employer for drivers in Chesapeake.
Top Trucking Companies in Chesapeake, VA
Here are our top recommendations for the best trucking companies to work for in Chesapeake:
Why Trust Freightwaves Checkpoint?
There's a reason we're one of the world's leading authorities on the global freight market. Our expert team has an in-depth understanding of the industry and is up-to-date on employment trends, regulations, and other insights into the trucking workforce.
We conduct thorough research and data analysis to develop our recommendations for the best trucking companies in Chesapeake. Every Chesapeake trucking firm is closely scrutinized based on its service range and capabilities. Our team also verifies companies' safety records and regulatory compliance and looks at what real users have to say about their experience.
From there, we narrow our focus to select only those top-performing and highest-rated firms to give you an informed and up-to-date list of the best trucking companies to work for in Chesapeake.
Sysco Hampton Roads, Inc.
7000 Harbour View BLVD, Suffolk, VA, 23435- Salary range: $100,000 - $150,000 in just the first year
- Routes: interstate
- Ongoing training: Paid CDL training
- Tuition reimbursement: true
- Power units: 71
- Drivers: 86
- Revenue: $320,612,000
- Miles driven: 1,846,512 (2023)
Sysco Hampton Roads, Inc. (DOT: 134515) was established in 1952 and operates out of Suffolk, Virginia. This organization functions primarily within the distribution sector, boasting a fleet size of between 20 to 49 vehicles. They transport a wide range of cargo, including beverages, chemicals, dry bulk commodities, fresh produce, meat, paper products, and refrigerated foods. The company is dedicated to hiring local, regional, and dedicated route drivers, including reefer and full truckload drivers.
Sysco Hampton Roads, Inc. takes pride in offering robust benefits for its drivers. Employees enjoy comprehensive health insurance packages, including dental and vision coverage, alongside life insurance and disability insurance. Sysco also provides retirement plans with a 401k, paid time off, and tuition reimbursement. Employees benefit from flexible scheduling, guaranteed home time, and additional perks like gym memberships and per diem payments. Competitive recruitment strategies include a notable sign-on bonus and a driver referral bonus program.
With an Indeed rating of 3.2 and a Glassdoor rating of 3.3, Sysco Hampton Roads receives mixed reviews from past and current employees. Positive feedback often highlights the company's competitive pay, which ranges from $100,000 to $150,000 within the first year, and the quality of the benefits packages. However, some employees express concerns regarding challenges in achieving a work-life balance and occasional disorganization in route assignments. The company's emphasis on ongoing training and development programs reflects its commitment to maintaining a skilled and proficient workforce.
Driver Options
- Regional
- Local
- Dedicated
- Reefer
Benefits
- Health insurance
- Dental insurance
- Vision coverage
- Health screenings
- Gym membership
- Life insurance
- Disability insurance
- 401(k)
- PTO
- Guaranteed home time
- Flexible scheduling
- Dedicated routes
- Ongoing training
- Tuition reimbursement
- Sign-on bonus
- Safety bonus
Safety
- Crashes: 6
- Unsafe driving: 0.39
- Driver fitness: 0.62
- Hours-of-service compliance: 2.12
- Vehicle maintenance: 3.16
- Controlled substances: 0.0
- Hazardous materials violations: 0
S.V. Trucking Services
2100 56th Sreet, Hampton, VA, 23661- Salary range: $55,000-$65,000
- Routes: intrastate non-hazardous
- Ongoing training: Paid CDL training
- Power units: 2
- Drivers: 2
- Miles driven: 100,000 (2024)
- Glassdoor:
- Indeed:
S.V. Trucking Services (DOT: 1324293) is a pivotal player in the trucking industry. Although the exact founding date isn't specified, the company is situated in Hampton, Virginia. They operate primarily in non-hazardous intrastate freight. S.V. Trucking Services carries a diverse array of cargo including building materials, fresh produce, general freight, grain feed, hay, machinery, meat, metal sheets, and refrigerated foods. The company primarily hires regional, local, over-the-road, and reefer drivers, excluding team, hazmat, or owner-operator positions.
Employees of S.V. Trucking Services benefit from a competitive suite of offerings that makes the company an attractive workplace. They offer health, dental, and vision insurance, supplemented by life and disability insurance. There are significant perks like a sign-on bonus, safety bonuses, and a 401(k) retirement plan with direct deposit available for drivers. With a commitment to a satisfactory work environment, employees enjoy guaranteed home time and ongoing training programs to enhance their skills and career progression.
S.V. Trucking Services boasts strong employee review scores, with a 4.2 on Indeed and 4.1 on Glassdoor, indicating general satisfaction among its workforce. Positive feedback often highlights the company's supportive work culture, stellar compensation package, and employee benefits. However, some employee critiques mention challenges regarding flexible scheduling and occasional organizational inefficiencies on routes. Overall, the company's reputation as an employer is bolstered by its focus on safety and driver satisfaction.
Driver Options
- OTR
- Regional
- Local
- Flatbed
- Reefer
Benefits
- Health insurance
- Dental insurance
- Vision coverage
- Life insurance
- Disability insurance
- 401(k)
- PTO
- Guaranteed home time
- Ongoing training
- Deadhead compensation
- Rider & pet allowances
- Sign-on bonus
- Safety bonus
Safety
- Crashes: 0
- Unsafe driving: 0.0
- Driver fitness: 0.0
- Hours-of-service compliance: 0.0
- Vehicle maintenance: 2.4
- Controlled substances: 0.0
- Hazardous materials violations: 0
Mike Fink
2700 Victory BLVD, Portsmouth, VA, 23703- Salary range: $50,000-$70,000
- Routes: intrastate non-hazardous
- Ongoing training: Paid CDL training
- Power units: 8
- Drivers: 6
- Miles driven: 85,000 (2024)
Mike Fink (DOT: 368063) is a Virginia-based trucking company located at 2700 Victory Blvd, Portsmouth, VA, 23703. This company specializes in transporting dry van and flatbed freight, and it primarily operates within intrastate non-hazardous regions. They hire full truckload (FTL), less than truckload (LTL), and last mile drivers. Founded as part of the vibrant transportation industry, Mike Fink employs a fleet of 8 trucks and maintains a focus on efficient, reliable delivery services.
The company offers a competitive salary range between $50,000 and $70,000 for its drivers, with added perks such as a sign-on bonus and guaranteed home time. Mike Fink prioritizes employee well-being with comprehensive health benefits, including medical, dental, and vision insurance, as well as PTO and a 401k retirement plan. Drivers are also eligible for safety bonuses and ongoing training and development programs, underpinning the company's commitment to safety and professional growth.
With a strong employee rating, Mike Fink scores 4.2 on Indeed and 4.0 on Glassdoor, reflecting a positive work culture that emphasizes job security and compensation. Positive feedback often highlights their supportive management and consistent home time, while negative feedback occasionally mentions limited advancement opportunities and room for improvement in work-life balance. Overall, Mike Fink is recognized for its dedication to maintaining a professional and rewarding workplace for its employees.
Driver Options
- OTR
- Local
- Flatbed
- Reefer
Benefits
- Health insurance
- Dental insurance
- Vision coverage
- Life insurance
- 401(k)
- PTO
- Guaranteed home time
- Ongoing training
- Rider & pet allowances
- Sign-on bonus
- Safety bonus
Safety
- Crashes: 0
- Unsafe driving: 0.0
- Driver fitness: 0.0
- Hours-of-service compliance: 0.0
- Vehicle maintenance: 0.0
- Controlled substances: 0.0
- Hazardous materials violations: 0
Tidewater Express, Inc.
1749 W Pembroke Ave, Hampton, VA, 23661- Salary range: $45,000-$55,000
- Routes: interstate
- Ongoing training: Paid CDL training
- Power units: 6
- Trailers: 4
- Drivers: 46
- Revenue: $530,000
- Miles driven: 460,000 (2023)
Tidewater Express, Inc. (DOT: 621518) was founded in Hampton, Virginia. The company operates within the trucking industry as both a carrier and shipper, primarily engaging in interstate operations. They specialize in transporting a variety of goods, including general freight, machinery, large objects, motor vehicles, and those requiring dry van and flatbed capacity. Tidewater Express focuses on hiring experienced drivers for over-the-road (OTR) opportunities, with particular emphasis on team and reefer drivers, ensuring they can cater to the diverse needs of their customer base.
Drivers at Tidewater Express benefit from a supportive work environment with comprehensive benefits packages, including health insurance with dental and vision coverage, paid time off, and a retirement 401(k) plan. Although they do not offer sign-on bonuses or tuition reimbursement, the company invests in ongoing training and development programs to foster professional growth. Tidewater Express takes a forward-looking approach by introducing programs aimed at gradually attracting new drivers into the industry.
Employee feedback showcases Tidewater Express as a generally positive workplace, receiving an Indeed rating of 4.0 and a Glassdoor-like rating of 3.8. Employees praise the company for its fair compensation and benefits but occasionally mention challenges with work-life balance due to the demands of the trucking industry. Some drivers note the lack of guaranteed home time, indicating an area of potential improvement. Nonetheless, Tidewater Express is viewed as a company dedicated to safety and employee development.
Driver Options
- OTR
- Regional
- Team
- Flatbed
- Reefer
Benefits
- Health insurance
- Dental insurance
- Vision coverage
- Life insurance
- Disability insurance
- 401(k)
- PTO
- Ongoing training
Safety
CSA safety score: Satisfactory
- Crashes: 2
- Unsafe driving: 0.66
- Driver fitness: 0.11
- Hours-of-service compliance: 0.0
- Vehicle maintenance: 0.0
- Controlled substances: 0.0
- Hazardous materials violations: 0
Rail Direct Transportation Company
801 Broad Street Suite 201, Portsmouth, VA, 23707- Salary range: $45,000-$55,000
- Routes: interstate
- Power units: 30
- Drivers: 28
- Revenue: $1,604,000
- Miles driven: 1,655,472 (2024)
Rail Direct Transportation Company (DOT: 706550) was founded in 1996 and is based in Portsmouth, Virginia. The company specializes in transporting general freight and intermodal containers, utilizing a fleet that includes dry van and flatbed trucks. Rail Direct Transportation Company primarily hires over-the-road (OTR) team drivers and local drivers to manage its interstate operations.
Known for its supportive work environment, Rail Direct Transportation Company offers employees a comprehensive benefits package that includes health, dental, and vision coverage, as well as life and disability insurance. Employees are also eligible for a retirement plan (401k) and paid time off. Although the company does not provide a sign-on bonus or tuition reimbursement, they do prioritize safety, reflected in their commitment to safety bonuses and maintaining a satisfactory safety rating.
With an Indeed rating of 4.2 and a Glassdoor rating of 4.0, Rail Direct Transportation Company is well-regarded for its positive work culture and reliable compensation. Employees frequently praise the company for its solid benefits and supportive management. However, some reviews point out areas for improvement, such as flexible scheduling and guaranteed home time, which are currently lacking or not meeting employee expectations. Overall, Rail Direct Transportation maintains a positive reputation among its workforce.
Driver Options
- OTR
- Local
- Team
Benefits
- Health insurance
- Dental insurance
- Vision coverage
- Life insurance
- Disability insurance
- 401(k)
- PTO
- Safety bonus
Safety
CSA safety score: Satisfactory
- Crashes: 1
- Unsafe driving: 0.23
- Driver fitness: 0.0
- Hours-of-service compliance: 0.0
- Vehicle maintenance: 5.7
- Controlled substances: 0.0
- Hazardous materials violations: 0
Best Way Transport, Inc.
6001 Miller Store Road Ste 102, Norfolk, VA, 23502- Salary range: $50,000-$60,000
- Routes: interstate
- Ongoing training: Paid CDL training
- Power units: 12
- Drivers: 9
- Revenue: $2,259,000
- Miles driven: 180,000 (2023)
Best Way Transport, Inc. (DOT: 568977) operates out of Norfolk, Virginia. Though exact founding details are not available, its operational data extends over an extensive period. The company specializes in transporting general freight and liquids/gases using a combination of dry van, flatbed, and reefer services. Best Way Transport, Inc. offers team driving opportunities and predominantly hires OTR and local drivers, including reefer and team drivers, to manage its fleet effectively.
Notable for its comprehensive employee benefits, Best Way Transport, Inc. provides full health insurance, dental, vision, and life insurance. Employees also benefit from a robust retirement plan with a 401(k) option, paid time off, and safety bonuses, reflecting the company’s commitment to driver welfare and satisfaction. The company's ongoing training and development programs further enhance the skills and growth potential of its employees.
With a Glassdoor rating of 4.0 and an Indeed rating of 3.1, Best Way Transport, Inc. receives mixed reviews from its employees. Positive feedback highlights the competitive compensation and benefits, while some criticisms point to areas needing improvement, such as scheduling flexibility and guaranteed home time. Despite these challenges, the company maintains a strong reputation for job security and a supportive work culture.
Driver Options
- OTR
- Local
- Team
- Reefer
Benefits
- Health insurance
- Dental insurance
- Vision coverage
- Life insurance
- Disability insurance
- 401(k)
- PTO
- Ongoing training
- Safety bonus
Safety
- Crashes: 0
- Unsafe driving: 0.0
- Driver fitness: 0.0
- Hours-of-service compliance: 0.0
- Vehicle maintenance: 0.0
- Controlled substances: 0.0
- Hazardous materials violations: 0
N.S. Trucking
1501 Twin Oaks Lane Apt 103, Virginia Beach, VA, 23454- Salary range: $55,000-$65,000
- Routes: interstate
- Power units: 1
- Drivers: 1
- Miles driven: 10,000 (2023)
N.S. Trucking (DOT: 855996) is a freight carrier based in Virginia Beach, Virginia. While the specific founding date is not listed, the company operates with a modern fleet primarily engaged in interstate transport. N.S. Trucking specializes in carrying a diverse range of cargo, including agricultural and farm supplies, beverages, building materials, commodities, dry bulk, construction materials, fresh produce, general freight, grain, machinery, metal sheets and coils, paper products, refrigerated food, U.S. mail, and utilities. They are known for hiring a variety of drivers, including OTR, reefer, tanker, and flatbed drivers, offering team driving opportunities and dedicated routes.
Among the benefits offered by N.S. Trucking are a competitive sign-on bonus, safety bonuses, health insurance, dental and vision coverage, paid time off, and a robust retirement plan with 401(k) options. The company emphasizes driver satisfaction with guaranteed home time, although certain benefits, like allowing passengers or pets and offering ongoing training and development programs, are not provided. Despite these limitations, N.S. Trucking has managed to maintain a strong reputation for their comprehensive benefits package.
Employee reviews on Indeed give N.S. Trucking a rating of 4.2, while their Glassdoor rating is 4.0, highlighting high levels of satisfaction in compensation, benefits, and job security. Positive feedback often praises the work culture and benefit offerings, though some employees note that work-life balance can be a challenge and that route assignments may sometimes lack organization. As the company continues to grow, they aim to address these challenges to further enhance driver satisfaction.
Driver Options
- OTR
- Local
- Dedicated
- Team
- Flatbed
- Tanker
- Reefer
Benefits
- Health insurance
- Dental insurance
- Vision coverage
- Life insurance
- 401(k)
- PTO
- Guaranteed home time
- Dedicated routes
- Sign-on bonus
- Safety bonus
Safety
- Crashes: 1
- Unsafe driving: 10.0
- Driver fitness: 0.0
- Hours-of-service compliance: 0.0
- Vehicle maintenance: 0.0
- Controlled substances: 0.0
- Hazardous materials violations: 0
Service Transfer, Inc.
4101 Wilcox Street, Chesapeake, VA, 23324- Salary range: $55,000-$65,000
- Routes: interstate
- Power units: 267
- Drivers: 267
- Revenue: $12,076,000
- Miles driven: 18,000,000 (2024)
Service Transfer, Inc. (DOT: 139659) was established in 1970 and is located in Chesapeake, Virginia. The company operates primarily in the transportation industry, carrying general freight and intermodal containers. They are equipped with a fleet of dry vans and flatbeds to handle a variety of cargo, and they primarily hire flatbed and over-the-road (OTR) drivers.
Service Transfer, Inc. offers competitive driver benefits, including health, dental, and vision insurance, as well as a retirement 401(k) plan and paid time off. Although they do not provide a sign-on bonus or guaranteed home time, they support new driver programs to help entrants transition into their roles. Despite not allowing passengers or pets, they maintain a modern fleet with an average age of three years.
On Glassdoor, Service Transfer, Inc. receives a high rating of 4.2, with employees praising the company for its fair compensation and benefits, as well as the supportive work environment. However, reviews on Indeed, which average around 3.8, highlight concerns regarding the lack of flexible scheduling and sometimes insufficient home time. Overall, employees appreciate the company's robust health coverage and retirement plans, although some express a desire for more structured driver support programs.
Driver Options
- OTR
- Local
- Flatbed
Benefits
- Health insurance
- Dental insurance
- Vision coverage
- Life insurance
- Disability insurance
- 401(k)
- PTO
Safety
CSA safety score: Satisfactory
- Crashes: 33
- Unsafe driving: 1.8
- Driver fitness: 0.01
- Hours-of-service compliance: 0.17
- Vehicle maintenance: 3.64
- Controlled substances: 0.0
- Hazardous materials violations: 0
Davis Trucking
305 Reflecting Ln, Hampton, VA, 23666- Salary range: $55,000-$65,000
- Routes: interstate
- Ongoing training: Paid CDL training
- Power units: 1
- Drivers: 1
- Miles driven: 1 (2022)
Davis Trucking (DOT: 459004) is situated in Hampton, Virginia. The company specializes in hauling a diverse array of cargo, including beverages, fresh produce, meat, general freight, and refrigerated foods. Though the exact founding date is not provided, Davis Trucking stands out with their focus on full truckload and less-than-truckload (LTL) services. They pride themselves on their fleet's youthful average age of three years and hire drivers in operations such as flatbed, reefer, and dry van trucking, particularly for over-the-road and local routes.
Davis Trucking emphasizes driver benefits, offering a competitive salary range of $55,000 to $65,000. Drivers can expect guaranteed home time, health insurance coverage including dental and vision, disability insurance, and a retirement plan with a 401(k) option. The company also incentivizes drivers with sign-on bonuses and safety bonuses. Although they don't allow for passengers, the company embraces a driver-friendly approach with ongoing training and development programs.
The company has garnered solid employee feedback with an Indeed rating of 4.2 and a Glassdoor rating of 4.0. Employees frequently commend the company for its comprehensive benefits package and consistent home time, contributing to a positive work environment. However, some reviews suggest the need for improved flexibility in scheduling to enhance work-life balance. Despite these challenges, Davis Trucking remains a respected and well-regarded player in the trucking industry.
Driver Options
- OTR
- Local
- Flatbed
- Reefer
Benefits
- Health insurance
- Dental insurance
- Vision coverage
- Life insurance
- Disability insurance
- 401(k)
- PTO
- Guaranteed home time
- Ongoing training
- Rider & pet allowances
- Sign-on bonus
- Safety bonus
Safety
- Crashes: 0
- Unsafe driving: 0.0
- Driver fitness: 0.0
- Hours-of-service compliance: 0.0
- Vehicle maintenance: 0.0
- Controlled substances: 0.0
- Hazardous materials violations: 0
Sapphire Courier Service, Inc.
1616 Centerville Turnpike #207, Virginia Beach, VA, 23464- Salary range: $45,000-$55,000
- Routes: interstate
- Power units: 4
- Drivers: 6
- Revenue: $1,098,000
- Miles driven: 485,000 (2023)
- Glassdoor:
- Indeed:
Sapphire Courier Service, Inc. (DOT: 813738) is headquartered in Virginia Beach, Virginia. The company specializes in courier and delivery services, primarily operating within the general freight sector. Despite the absence of an exact founding date, Sapphire Courier Service has established itself with a fleet size of 4 trucks and 8 trailers, while employing and hiring local as well as over-the-road (OTR) drivers.
Sapphire Courier Service offers a range of benefits that make working for them appealing. Employees receive health and dental insurance, life insurance, vision coverage, paid time off, and a retirement plan (401k). However, there are no sign-on bonuses or driver referral bonuses currently available. While they do not expressly allow passengers or pets, their employee-focused benefits establish a supportive work culture.
On Glassdoor and Indeed, Sapphire Courier Service maintains favorable ratings, with scores of 4.0 and 4.2, respectively. Employees frequently commend the company’s solid compensation and benefits packages. However, some critiques highlight the lack of guaranteed home time and limited flexible scheduling as areas for improvement. Overall, employee feedback suggests a generally positive work environment with room for growth and advancement.
Driver Options
- OTR
- Regional
- Local
Benefits
- Health insurance
- Dental insurance
- Vision coverage
- Life insurance
- Disability insurance
- 401(k)
- PTO
Safety
- Crashes: 0
- Unsafe driving: 0.0
- Driver fitness: 0.0
- Hours-of-service compliance: 0.0
- Vehicle maintenance: 0.0
- Controlled substances: 0.0
- Hazardous materials violations: 0
What To Look for in Chesapeake Trucking Companies
In Chesapeake, VA, the trucking company you choose can greatly impact your career satisfaction and success. Be sure to consider these important points when reviewing potential employers in Chesapeake:
- Pay range & career growth: A good paycheck is only the start — make sure you’ll have room to grow. Search for Chesapeake trucking employers that offer skill-building programs, raise opportunities tied to training, and clear advancement paths with bonus incentives.
- Benefits: The best benefits go beyond the basics. Consider companies with added perks like employee stock plans, deadhead pay, and lease-to-buy options, which show they value long-term employee success.
- Culture: Look for Chesapeake companies that make work-life balance a priority, offering extras like pet and rider allowances or regular time off on weekends.
- Employee feedback: Pay attention to which companies receive praise from employees for being fair, supportive, and a great place to build a career.
Types of Driving Jobs Available
In Chesapeake, you’ll find many trucking job options tailored to your skills, experience, and preferred work style:
- Long-haul: Suited for those who enjoy lengthy trips and traveling to distant cities, sometimes across the entire country.
- Regional: Offers routes that keep you within Virginia and nearby states, letting you return home more often than long-haul.
- Local: Provides consistent, short-distance routes inside Chesapeake and its surrounding areas.
- Specialized: Involves transporting niche cargo types like liquids, frozen goods, or dry freight within Chesapeake’s unique shipping industry.
How To Choose the Right Company for Your Career Goals
As you decide on the best trucking company in Chesapeake for your career path, be sure to:
- Make a list of what matters most. Decide if income, health benefits, flexible scheduling, or preferred routes will influence your decision the most before you start applying.
- Look at local companies. Review the pay structures, benefit packages, and reputations of Chesapeake, Virginia trucking companies to see which ones stand out.
- Get input from drivers. Speak with local drivers about their personal experiences and use sites like Glassdoor and Indeed for further insights.
- Think about your career goals. If you're just starting out, CDL sponsorship and skill development opportunities may be crucial. For seasoned drivers, long-term stability and advancement options may take priority.
How To Apply
Ready to start your trucking career in Chesapeake? Here's how you can apply to the top companies:
- Update your resume. Make sure to highlight your driving experience, certifications, and any specific skills that are relevant to the local job market.
- Research companies. Visit their career pages to see available job openings and learn about their work culture in Chesapeake.
- Submit your application. Apply directly online through the company's website or job boards like Indeed and Glassdoor.
- Follow up. After applying, follow up with recruiters to show your continued interest and ask about the next steps.
Frequently Asked Questions
Below are answers to common questions truck drivers have when considering trucking companies in Chesapeake:
Is a truck driving career worth it in Chesapeake?
A truck driving career in Chesapeake can be highly rewarding, especially with the growing demand for freight movers in the area. Drivers can earn competitive wages, enjoy job security, and find plenty of opportunities for career growth in the local trucking industry.
Which company in Chesapeake offers the best benefits for long-haul drivers?
Sysco Hampton Roads, Inc. is known for excellent long-haul benefits, including health insurance, retirement plans, and bonuses.
What type of driving jobs are most available in Chesapeake?
Most trucking companies in Chesapeake are hiring for regional and local driving positions, with some also offering specialized roles for more experienced drivers.
What is the best trucking company for new drivers in Chesapeake?
Sysco Hampton Roads, Inc. is known for its exceptional paid CDL training and offers strong career support for new drivers starting out in Chesapeake.