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Trucking Insurance in Annapolis, MD

Trucking Insurance

Protection you need and Coverage you can afford


Businesses that depend on vehicles to get the job done need insurance to protect against the risks that drivers and other employees face.  Whether it’s a collision, weather-related damage, or equipment-related loss, insurance protects trucking businesses from liabilities that cause financial peril. 


At Old Bay Insurance, we understand the risks and exposures that truckers and trucking businesses face and we know how to mitigate these risks and exposures through insurance solutions.  We also understand that not all insurance providers are the same.  We are independent, which means that we have the ability to specialize.  Specialization results in meaningful coverage. 


For your business, accept no less than customized coverage tailored exactly to your needs.  Also, ensure that your agent knows the details of your situation, market, and operations.  These details are keys to proper coverage.  At Old Bay we make detailed assessments of each client’s needs and situation fundamental elements of our products and services.  For this reason and others, we are one of the most successful and trusted trucking insurance providers in the Midwest. 


Who do we cover and what Coverages do we provide?

Some of the coverages you buy are required by USDOT.  Others are required by state authorities or by shippers.  Sometimes you may need worker’s compensation and other times you may not.  You may need uninsured motorists insurance (UIM), personal injury protection (PIP), and bobtail insurance in some cases and not in others.  These and other coverages are important to consider but may not be essential.  It depends on your case.


At Old Bay we evaluate your unique situation and assign coverage to each element of your situation so that you are completely covered and pay minimal costs for the coverage.  Our coverage options include:



  • Primary Liability
  • General Liability
  • Bobtail Liability
  • Workers’ Compensation
  • Occupational Accident
  • Cargo
  • Physical Damage
  • Excess Liability
  • Owner Operators
  • Contingent Coverages
  • Fleets
  • Car haulers
  • Tow trucks
  • Long haul truckers


We have long list of optional coverages not mentioned above that protect you against liabilities that you face through your unique operations.  These options cover businesses in varying industries and that use different kinds of trucks.   Whether you’re an owner-operator, motor-carrier, private-carrier, or other; and whether you use box, semi, flatbed, or other trucks; we can help protect you. 


Our specialists will help you select coverage and outline all pertinent benefits and discounts.  They will also provide you with ongoing support. 


How is Old Bay Insurance Unique?


Value.  Time, money, and convenience of products and services all contribute to overall value.  An agency’s claims procedures should be easy to follow and the agency’s turnarounds should be quick.  The staff should be helpful, knowledgeable, and accessible.  In all cases, the agency should be prompt and should provide skilled assistance in protecting against risk, reducing accidents, and passing DOT audits.  They should do this without saddling you with extra charges.


The agency should be transparent.  When dealing with you, the agency should translate all terms, stipulations, and agreements into understandable language.  You should be empowered to make your own decisions.  An agency should not offer products at the lowest prices and claim that these products are equal to competitors'.  They should prove that you’re buying ‘peace-of-mind’ by helping you compare their coverage to competitors’ and by providing exceptional services.


At Old Bay, we prove it with every product and in every service provide.  We do more than provide you with coverage; we help you file claims, maximize discounts and benefits, offer comprehensive quotes, and lower the frequency and severity of losses.  We also protect your company’s assets by emphasizing the link between good driving and cost reduction.  In the event of an incident, a full-time, dedicated claims manager will make it easy to report a loss, track its status, and receive prompt payment. 


We keep your business moving forward.  From determining the right deductibles and coverage limits to helping your employees operate more safely, we provide products and services that give you confidence.  We have been doing it for more thirty years, and there is nothing that gives us more satisfaction than helping a business operate successfully.  The pride and joy that we take in this is expressed in every service we provide.  


Please contact us today to find out more about how we help secure your operation.

Old Bay Insurance Agency - Main Office

133 Defense Hwy, Suite 214

Annapolis, MD 21401

Main office: 410-777-5390
Fax: 410-774-5240

Office Hours:

Mon: 9:00 AM - 5:00 PM
Tues: 9:00 AM - 5:00 PM
Wed: 9:00 AM - 5:00 PM
Thurs: 9:00 AM - 5:00 PM
Fri: 9:00 AM - 5:00 PM
Sat: Closed
Sun: Closed

Our Providers


Phil ROCKS! He not only saved us a TON of money on our insurance but is friendly & helpful with any & all reminders & questions! You will not be disappointed! Thank you for all that you do for us!
Megan Rosendale
Neal Tatterson is very knowledgeable and attentive. Going with Old Bay Insurance saved my family a bunch over our previous insurer.
Sean Lyon
Neal is Amazing! I have my business insured with him As he helps with all aspects and his speed of response on answers to questions and documents needed is quicker then ever expected and always appreciated. When running a business it is nice to have someone to count on!
Daniel Reall
Highly recommend this agency. Great prices and great service.
Samantha Tatterson
I've know Neal Tatterson for over 20 years. Always been a pleasure doing business with him. He is knowledgable about all aspects of insurance. I would highly recommend him as an agent
Albert Lee
Amazing Amazing Amazing!!! Neal Tatterson was a tremendous help saving us on our Flood Insurance ,(previous company had our elevation wrong), home owners, car and boat insurance policies. Over all it was close to $2,000 a year in savings.Yipee!!! I spread they great news to my neighbor, they switched all their policies as well for substantial savings in premiums.
David Mewshaw
I switched to Old Bay insurance years ago. Neal has always acted promptly and professionally to all my insurance questions and concerns. Regardless of the type of insurance, Old Bay, has numerous products that can be tailored to fit your needs and budget. I highly recommend them.
Randall Zyvoloski
Neal Tatterson and Old Bay Insurance have been fantastic to work with over the years. Neal is always prompt in his replies to my requests and always finds ways to get my family exactly what we need for our insurance needs. I highly recommend Neal and his company!
Joe Burcham
Amazing service! Got me set up with insurance speedily and efficiently. Very helpful in laying out the options and letting me decide what best suited my needs.
Elizabeth Anne Odell
We moved our policies over to Old Bay Insurance around 3 years ago and have not looked back. Neal and his team have worked hard to ensure that we have the best packages for all of our rentals and business/personal needs. They even helped us with advising our neighbor (who was not a client) when their house caught fire. I highly recommend Old Bay Insurance!
Julie Mast
Neal and company have superseded great customer service. He produced the best products to meet my family's needs. Hands down, best insurance advocate you can get. Thank you.
Anthony Jordan
Neal was great. Always promptly emailed me back when it was needed, called when I asked him to do so. Was flexible with my insurance quotes. As a first time home buyer I had a ton of questions about having my own insurance. Neal answered them as quickly and truthfully. Highly recommend this agency to anybody looking for one. You won't go wrong.
Matthew Thomas
Old Bay Insurance Agency has always taken phenomenal care of my family! The company has consistently put my needs first. The employees are personable and efficient. Every experience I've had with Old Bay has exceeded my expectations. I would highly recommend this insurance agency because of their genuine concern for their customers!
Kate Gicking
Neal is a great and reliable resource to both my wife and me. I am very grateful for his help and guidance in times both good and bad. He is quick to answer a phone call and email and has a great personal touch. I highly recommend Neal to all my friends and family.
Robert Gicking
Totally professional, answered everything and saved me a bunch of money.
Frank Black
Neal has saved us money while providing optimal insurance coverage for our family. He is very knowledgeable and quickly responds to any questions that arise regarding our insurance needs. We are very happy with Old Bay's professional and prompt service. When we had an auto claim, they thanked US for being a valued customer! We didn't have to worry about a thing during the claim's process. So go with Old Bay. Neal will take good care of you!
Leigh Ann Miller
AWESOME, AWESOME, AWESOME ! Since finding Old Bay Insurance, I have not desired to go no place else! I am confident in saying that Neal has been there for every type of commercial insurance that I have requested. Being a new business owner comes with a lot of insecurities, but finding an agent that does it all and can be counted on as " always being there" has definitely turned into a blessing. If I might add, I am always satisfied with the quotes that I receive which further helps me to conclude that he has searched for the best rate possible! I am an actual client and am extremely satisfied with my experience and growing business relationship with Neal of Old Bay Insurance!!!!
Building Bondz Kids Services
I have dealt with a series of "big box" insurance companies, and been loyal to each of them in turn, only to have (especially in the most recent instance) a series of impersonal "representatives" with whom I had little or no contact unless there was an issue (and even then, they changed so frequently that it was like starting all over again). Imagine my delight at having a real insurance agent, someone who took the time to understand me and my needs, and help me find the best coverage for my situation! I can't praise Neal's warmth, competence, and honesty enough! I really feel that, this time, I have someone I can trust (rather than someone whose name I barely remember, and need not memorize, because it will be likely to change tomorrow), and someone who sees me as a person rather than as an "account." I'd recommend Old Bay without reservation to anyone who is tired of dealing with the corporate monolith, and wants to interact with a caring human being again.
Phoenix Rising
Quick and easy - Neal made the whole process of getting set up with auto insurance completely effortless! A++
Kyle Barry
GoodHe was so active and conveyed a lot of useful information's.
Justin Judith
Excellent service by Neal Tatterson. I am happy for being your customer.
John Johnson
Neal is very professional and courteous. I used this company for my last two home purchases and highly recommend them for their insurance quote prices and their lightning-fast responses to any of my questions.
Stephen Van Devender
For several years I was looking for an insurance company. I found Neal and Old Bay Insurance and gave them a shot. They took my business. Over the years there was a choice for us to make. Stay with Neal and change my carrier, or stay with my carrier and let Neal go. We considered and decided to stay with a local business , Old Bay Insurance. We have been satisfied with this decision. and now Endorse Neal and Old Bay Insurance. Our feelings are work with local business. We consider where our money goes. And how it is used. We want local companies to develop and local lives to prosper. And from this though process today years later we are happy with our choice of insurance provider. Of note Neal has grown with us in his customer service. Which is important to us. We do endorse Old Bay Insurance and Neal Tatterson.. And are satisfied with their work and product.
Terry Black
Neal and his team are so wonderful to work with, you can even text with them if you need anything. They were able to lower my auto insurance rates, and do the same for my brother and a good friend of mine - all with great coverage. Highly recommend them for anyone looking for an independent insurance company.
Niki Rogers
Neal Tatterson reviewed my insurance coverage and was able to lower my cost by 50%!!! Old Bay Insurance Agency has amazing customer service. I will be referring all my friends and family to Neal and his team!!
Leticia Bustamante Guzman
Neal is awesome - and he looks so suave in his picture. Kinda like a secret agent, agent.
Erik Lytikainen
Neal was a great help switching our insurance and saved us about $400.00 this year!! We highly recommend Old Bay Insurance!
Jennifer Tollberg-Van Breevoort
Neal did a great job with helping my daughter switch her auto to a lower rate and got her homeowners insurance. All was done fast and precise.
Mary Stokes
I just wanted to drop you a short line and thank you for always being their for our families' insurance needs. First off, you have been our agent through many transitions and challenging times, whether it be a car accident or just questions about how to proceed next. You have been our agent for about 15 years and I would never change insurance agents, as you are the best!!! You always seem to have the answer to whatever issue comes up and the resources and ability to solve it quickly. Case in point, when I called yesterday to ask you a question about the MVA and a recent letter they had sent me, you said let me check it out on the internet and then call them directly. Within twenty minutes you called me back to say that it was all worked out and that it was just a mistake in their computer file for our car. That saved me the potential headache and aggravation with having to make a personal visit to the MVA to resolve the situation. Thank you for that and so many other situations that you have helped us out on through our long relationship. The other thing that I have to say is that working with Allied Insurance has been quite wonderful as well. I always liked Erie insurance too when we were with them for all those years. I have to say though, the ease of contacting them and paying my bill or talking to an agent on the phone, has always been easy and pleasurable and I like them even more than Erie. You teamed up with Allied, makes a pretty amazing combination for anyone's insurance needs!!! Thanks as always and peace to you and your family.
Chris Luzier