Locally Inspired Insurance™

Insurance, Handled Personally


At Insurance Outfitters®, we do insurance differently. We’re not a franchise. Not a faceless call center. We’re a locally grown, community-rooted team based in Shepherdstown, WV—and we’ve been earning our neighbors’ trust since 1989.
Whether you need home coverage, a million-dollar umbrella, or specialty protection for your distillery, we’ll match you with the right policy and walk you through it like a neighbor, not a salesman.

Contact Us

Read our Privacy Policy. 

What We Offer

We work with individuals, families, and business owners across West Virginia, Maryland, North Carolina, Pennsylvania, Tennessee, and DC. Here’s what we specialize in:

A black and white shield with a person 's face inside of it.

Personal Insurance

A black and white check mark in a square on a white background.

Homeowners

A black and white check mark in a square on a white background.

Auto

A black and white check mark in a square on a white background.

Umbrella Liability

A black and white check mark in a square on a white background.

Life

A black and white check mark in a square on a white background.

Classic Cars

A black and white check mark in a square on a white background.

Motorcycles & Boats

A black and white check mark in a square on a white background.

Vacation & Rental Properties

A black and white icon of a bottle with a lightning bolt and a shield.

Business Insurance

A black and white check mark in a square on a white background.

Small Business Coverage

A black and white check mark in a square on a white background.

Distillery & Brewery Insurance

A black and white check mark in a square on a white background.

Liability, Property, Auto & More

Why Choose Us

Local, Boutique Service

Every quote comes from a real person—usually Tom, not an automated system.

Five-Star Reputation

Over 170 Google reviews. All five-star. All real.

Referral-Driven Trust

We’re the go-to agency for local lenders and new residents alike.

Trusted by over 175 5-star reviews

clients worldwide

A woman is standing in front of a red wall in a circle.
A black and white cat is laying on top of a woman 's head.
A man wearing sunglasses and a bandana is in a circle.

Insurance Outfitters of Shepherdstown is the very best and only place you should be shopping for your insurance needs!! My wife and I have been a client for many, many years and they have never failed to meet our needs for auto and home insurance coverage. No matter our questions, they always had the answer and explanation. Always priced exceptionally well, but just as important, guided us through the buying process to ensure we had exactly the proper coverage to protect our assets. Each insurance product was tailored exactly to our needs. We never felt it was just a "rubber stamped" package and process to sell insurance. It was always the personal touch. Give them a call and be surprised at how enjoyable buying insurance can be.

John T.

Satisfied Client

If you’re looking for someone to guide you through the investing process, Tom is your guy. He sat down with us and thoroughly explained how the process works and which options would fit our needs. Fun and courteous to work with. He showed us how his rates compare with other institutions but never pressured us on decision making.

Dave S.

Satisfied Client

I've had my flood insurance for my home through Insurance Outfitters for several years now. I've worked several times with Shelley and others in setting up and making changes to the policy (never a claim - knock on wood!), and everyone in the office are always very helpful, quick to respond, and extremely nice to work with. Their rates are also really good compared with other quotes I've received. I highly recommend Insurance Outfitters!

Elizabeth P.

Satisfied Client

Licensed States


We are proud to be fully licensed in:
A black map pin icon on a white background.

West Virginia

A black map pin icon on a white background.

Maryland

A black map pin icon on a white background.

Pennsylvania

A black map pin icon on a white background.

North Carolina

A black map pin icon on a white background.

Tennessee

A black map pin icon on a white background.

District of Columbia

Stay Informed With Our Blog

Explore the Blog for expert advice, industry updates, and tips on insurance and risk management.

More On Our Blog
There are footprints in the sand on the beach near the ocean.
By duda September 5, 2023
The new season is a great reason to make and keep resolutions. Whether it’s eating right or cleaning out the garage, here are some tips for making and keeping resolutions.
A man is walking past a blue food truck on the side of the road.
By duda September 5, 2023
There are so many good reasons to communicate with site visitors. Tell them about sales and new products or update them with tips and information.
A woman is drinking a cup of coffee in a park.
By duda September 5, 2023
Write about something you know. If you don’t know much about a specific topic that will interest your readers, invite an expert to write about it.
Ready to chat?

Ready to Start a Quote?

It’s easy—just a name, contact, and what you need help with. We’ll take it from there.