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Insurance Outfitters

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Shepherdstown, WV
Insurance Outfitters

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Founded March 3, 1989, Insurance Outfitters® is award-winning and family-owned, independent insuran Our goal is to write insurance in all 50 states.
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Due to extensive online advertising, the unique & distinctive name, Insurance Outfitters®, is widely recognized by the general public in the United States. Today, we write insurance in the District of Columbia, Maryland, North Carolina, Pennsylvania, Tennessee, Virginia, and West Virginia. Since its founding on March 3, 1989, this award-winning, family-owned, independent insurance agency has grown from a one-person operation to a team of motivated, high achievers committed to delivering innovative and tailored risk management solutions from Shepherdstown, West Virginia, to protect individuals, organizations and businesses. Our founder & CFO, Tom Maiden, is a Captain (select) in the Navy Reserve, an Iraq war veteran, a CERTIFIED FINANCIAL PLANNER™ practitioner, and Chartered Life Underwriter®, specializing in risk management & insurance planning. He has a Master of Business Administration degree from West Virginia University and over 32 years of experience. Co-owner, Michele Ours Maiden, joined the family business after serving 23 years in management with Pfizer, one of the world's premier innovative biopharmaceutical companies. She has a Master of Business Administration degree from Loyola University Maryland. When local consumers have a risk management or insurance planning related question, their friends and neighbors will answer, “Ask Insurance Outfitters®!”

Insurance Outfitters® is committed to building safer, greener, better educated, diversified, and inclusive communities where we serve. Our intent is to be a good corporate citizen. The annual Insurance Outfitters® Guide Awards are scheduled around our anniversary, March 3rd, every year. The Insurance Outfitters® Guide Awards was developed to thank those people and organizations who may not make the front page news, but who change the world around us for the better in the following categories:
1. Conservation and Outdoor Recreation
2. Health and Human Services
3. Education
4. Culture and the Arts

Insurance Outfitters® has built a reputation for being honest, ethical, genuine, energetic, and reliable. All of the guides at Insurance Outfitters® are committed to delivering exceptional customer experiences, individualized service, and a deeper appreciation of what “locally inspired” means. As a matter of fact, our tagline is, Locally Inspired Insurance®.

10/27/2026

This Halloween, the scariest thing your business can face is not a ghost or goblin — it is finding out too late that your policy does not cover what you thought it did. From cyber threats to liability claims, the risks that haunt businesses most are the ones nobody planned for.

This month, let's keep the unexpected frights to the haunted houses! Give us a call today for a complimentary portfolio review.

10/24/2026

Michele & Tom Maiden’s Insurance Outfitters® would like to thank The Rotary Club of Shepherdstown for making our fall 2026 Adopt-a-Highway roadside cleanup a success! We collected 20 bags of trash along Martinsburg Pike between the Shepherdstown Fire Department and the Berkeley County line.

10/20/2026

As the days get shorter, deer become much more active and are more likely to cross roadways — especially around dawn and dusk. This increased activity can pose serious risks to drivers, and hitting a deer can be a distressing and upsetting experience.

With that in mind, our team wants to share a few reminders to help keep you and your passengers safe this season and navigate the aftermath of striking a deer. Swipe for more.

If you're not sure what your current policy includes or would like to review your coverage this fall, feel free to reach out. Our team would be happy to answer your questions and help you understand your options.

10/15/2026

Most homeowners or drivers have some form of homeowners and auto insurance; however, their coverage might not be enough to protect them in the event of a major claim.

When a serious accident or unexpected lawsuit exceeds what your existing policies can cover, the gap between what you owe and what your insurance pays becomes very real, very fast. That’s where umbrella liability coverage comes in.

Umbrella liability insurance covers costs that would otherwise come straight out of your pocket. With relatively low annual costs, this comprehensive coverage can be one of the most affordable ways to fully protect what you love.

So, if you’re curious about whether umbrella insurance makes sense for your situation, please don’t hesitate to reach out to our team. We are here to help you run the numbers and see what makes sense.

10/06/2026

Cyber threats are not just a concern for large corporations. In fact, small- and mid-sized businesses often face increased risk. This Cybersecurity Awareness Month, we are sharing a reminder of a few practical ways to strengthen your cyber defenses.

Of course, even with strong prevention measures in place, a cyber incident can still happen, and the cost of recovery can add up quickly. Having the right cyber liability coverage can help your business respond more effectively.

Have questions about cyber insurance or want to review your current coverage? Reach out to our team today.

09/22/2026

Can you believe there are only 100 days left in the year? Before the final stretch gets away from you, it is worth pausing to ask one simple question: has your life changed this year?

A new car, a home purchase, a career change — these are the kinds of milestones worth celebrating. They are also the kinds of changes that can quietly create gaps in your insurance coverage if your policies have not kept up.

Here are some of the most common life events that can affect your coverage:

✅ You bought a new home or renovated your home. A new home purchase or extensive renovations require coverage that reflects the property's true replacement cost, not just its market value.

✅ You purchased a new car. Purchasing a new car is a change that always merits a check-in about your insurance coverage, especially if you purchased a car worth more than the vehicle you were previously driving.

✅ Your family or household situation changed. Marriage, divorce, welcoming a new child, adding a teen driver, sending a child off to college, or welcoming an adult child back home are all changes that can affect your auto and homeowners coverage.

✅ You’ve acquired new valuables or heirlooms. If you’ve recently obtained or inherited new jewelry, art, or other collectibles, it may be worth reviewing whether these items would be fully covered under your current homeowners policy.

✅ Your income, assets, or career changed. A promotion, a new job, a side business, or an inheritance can all increase your financial exposure in ways your current coverage may not reflect.

If any of these sound familiar, our team would love to take a few minutes to review your policies together and ensure everything still aligns with where you are now. It's a simple conversation that can make a real difference.

Feel free to reach out anytime. We are here to help ensure your coverage keeps up with your needs.

09/15/2026

Medicare Annual Enrollment begins October 15th, which means now is the time to watch for an important document from your current Medicare Advantage or Part D plan: your Annual Notice of Change (ANOC)

Typically mailed in September, and no later than September 30th, your ANOC outlines any updates that may take effect on January 1st. Even if you’ve been happy with your current coverage, reviewing these changes carefully can help you avoid unexpected costs or coverage gaps in the year ahead.

Your ANOC may include updates to:

✅ Monthly premiums and other out-of-pocket expenses.
✅ Prescription drug coverage and formularies.
✅ Doctor, hospital, and pharmacy networks.
✅ Copays, deductibles, and additional plan benefits.

Small plan changes can make a significant difference in your health care costs and provider access. Taking time to review your ANOC now can help you make more informed decisions during Medicare Annual Enrollment.

If you would like help understanding your plan changes or comparing your Medicare options before enrollment begins, contact us anytime. We are here to help you review your coverage and find a plan that fits your needs for 2027.

09/10/2026

Have you heard of term life insurance and are wondering if it might be right for you? Term life coverage is designed to provide a financial benefit to your chosen beneficiaries if you pass away during a selected coverage period, often 10, 20, or 30 years.

Here are a few reasons many people choose this type of coverage:

🔹It can be a good fit during life’s busiest financial years, when others may be relying on your income the most.

🔹Coverage may be more affordable when purchased earlier, as premiums are often based on factors such as age and health.

🔹You can choose coverage that aligns with your goals, like paying off a mortgage, supporting children through college, or preparing for retirement.

🔹It can provide protection at a lower cost, allowing individuals to obtain higher coverage amounts for a lower premium.

🔹 Some policies offer flexibility for the future, with options to convert to permanent life insurance later on.

If you’d like to explore coverage options or see what a policy may look like for your situation, feel free to reach out. We’d be happy to answer questions or put together a quote for you.

09/04/2026

We wish each of you a wonderful Labor Day! During this annual celebration of hard work, may you enjoy a well-deserved, restful break.

Please note that our office will be closed on Monday, September 7th, in observance of the holiday, and will reopen on Tuesday, September 8th.

08/26/2026

As you may know, it’s almost time for Medicare’s annual enrollment period (AEP). The Medicare AEP runs from October 15th to December 7th every year, making now a potentially advantageous time to review your current coverage and plan ahead for any changes next year.

Thinking about this now, before the period opens, can make the process easier and give you enough time to compare options and make an informed decision about your care. Swipe for a few areas to revisit as you prepare for the beginning of the AEP.

The AEP is your yearly opportunity to review your Medicare coverage and make changes for the next plan year. A little preparation now can make the process simpler and help you choose coverage that fits your needs. That said, if you’d like to go over your current plan, feel free to reach out. We are always here to help you carefully assess your needs so you can make an informed decision.

Address

7866 Martinsburg Pike
Shepherdstown, WV
25443

Opening Hours

Monday	9am - 5pm
Tuesday	9am - 5pm
Wednesday	9am - 5pm
Thursday	9am - 5pm
Friday	9am - 5pm

Telephone

+13048760822

Website

http://www.InsuranceOutfitters.com/

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