teenSMART® safety training that pays off
Smarter driving skills today can mean savings tomorrow.
Get StartedSimpson’s Olde Towne Insurance has over 50 years of experience in the insurance industry and takes pride in serving its Southern Maryland roots. Our agents are licensed in Maryland, DC, and Virginia and are ready to provide you with professional, friendly, and courteous service.
We offer personal insurance, business insurance, and life insurance products from a variety of reputable insurance companies to ensure we provide you the product that best fits your needs at the most affordable price. If you are ready to save some money on your insurance give us a call or stop in and see us. We are located on Route 301 just two miles south of La Plata. We look forward to serving you!




Posted: October 4, 2026
Every October, the Cybersecurity and Infrastructure Security Agency (CISA) leads Cybersecurity Awareness Month, a nationwide effort to help individuals and organizations better protect themselves online. For small and mid-sized businesses, it's also a timely reminder to think about how a cyberattack or data breach could affect operations, and whether cyber liability insurance has a role to play in your risk management plan. Why Cyber Risk...
Posted: October 2, 2026
Every October, the National Fire Protection Association observes Fire Prevention Week, which falls on October 4-10 in 2026. The observance began over a century ago to mark the anniversary of the Great Chicago Fire, and it remains a helpful reminder to check the basics of home fire safety before colder weather sends more people back to their stoves, fireplaces, and space heaters. Common Causes of...
Posted: September 19, 2026
Working for Yourself Comes With Its Own Insurance Needs More people than ever are working as independent contractors, consultants, or freelancers, whether as a primary career or a side business. While this type of work often offers flexibility, it also means you're generally responsible for your own insurance protection, since you likely won't have coverage through an employer. Taking time to understand your options early...
Posted: September 16, 2026
September Is a Popular Month for New Leases Many apartment leases and off-campus housing arrangements begin in September, as students head to college and young professionals relocate for new jobs. If you're moving into your first apartment this fall, renters insurance is worth understanding before you sign a lease, even though it's easy to overlook amid the excitement of a new place. What Renters Insurance...
Smarter driving skills today can mean savings tomorrow.
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