• Business Insurance

    Smallwood and Small’s “fit experts” tailor strategic solutions to your small business needs. Our employee benefit programs and commercial products ensure that your company—and your team—are safe, supported and suited for success.

    Business
  • Auto Insurance

    Life on the open road is full of twists and turns, but Smallwood and Small lets you enjoy the ride with confidence. We’ve been providing some of the best auto insurance in Martinsburg, West Virginia. Our experts customize your policy at “wheely” great rates—without compromising the coverage you deserve.

    Smallwood and Small
  • Home Insurance

    Whether you dwell in a dream home or a DIY labor of love, Smallwood and Small takes your domestic aspirations to heart. We’ve been supporting residents of the Eastern Panhandle with quality homeowners insurance for over 30 years.

    Smallwood and Small
  • Life Insurance

    Whether you’re setting the world on fire in your twenties or settling into your seventies, preparation is the true path to financial enlightenment. In an economic landscape characterized by high expenses and fewer holiday bonuses, we must enjoy the journey, but anticipate the destination.

    Smallwood and Small
  • We're in the Fan Zone

    Shepherd University and Smallwood and Small Insurance have agreed to a unique new comprehensive campuswide partnership program.

    Learn More »

Save with Bundling

Confused about your coverage? Get to know Jack about your insurance.

Who We Are

Smallwood and Small cuts tall problems down to size.

Your one-stop-shop for short and long-term life planning, Smallwood and Small creates integrated insurance solutions for your personal and business needs. From auto policies to annuities, homeowners’ policies to health insurance, our experts are seasoned, savvy and ready to serve customers in West Virginia’s Eastern Panhandle and throughout the tri-state region.

Solutions for Small Businesses

Learn More Smallwood and Small

Smallwood and Small

Approachable and Acclaimed

Learn More Smallwood and Small

Smallwood and Small

We Make Insurance EZ®

Learn More Smallwood and Small

Smallwood and Small

The Smallwood Scoop

travel insurance benefits

Travel Insurance Benefits

Posted on July 26, 2017

So you’ve just booked a trip across the country or perhaps to some far-away destination abroad. Time to kick back and start counting down the days until your […]

Read More

Travel Insurance Policies

Travel Insurance Policies

Posted on July 19, 2017

Know Before You Go If you live to vacation, you’re in mighty good company. In 2014, the U.S. Travel Association estimated that Americans spent $927.9 billion on travel. […]

Read More

123_2

Our Tribute to James Smallwood

Posted on July 11, 2017

The family of Smallwood and Small Insurance sadly announces the passing of one of its founders, Mr. James W. Smallwood. He passed away on July 4th and was […]

Read More

Quick Quote

Get the Smallwood and Small solution.
For excellent service and cost saving insurance, request a custom quote today!