In celebration of the New Year, we will close at Noon on Thursday December 30th and all day Friday December 31st. Be safe this New Year's Eve.

Auto Insurance

Roads may be full of twists and turns, but your insurance coverage & premiums shouldn't be! We'll find you the best protection at affordable rates.

Protect Your Vehicles Today

Home Insurance

Whether you dwell ina 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.

Protect Your Home & Belongings

Business Insurance

Strategic solutions to your small business needs. Our employee benefit program and commercial products ensure that your company - and your team - are safe, supported, and suited for success.

Protect Your Business & Employees

Life & Disability Insurance

Life is short. While we want you to play hard, we also want you to think hard about the legacy you’ll leave behind—especially if you’re injured on the job or if you pass unexpectedly. Life and disability insurance are simple, economical ways to plan ahead while enjoying the now.

Protect Your Family

Medicare Insurance Plans

Navigating Medicare can feel overwhelming, but we’re here to help make it simple. We offer guidance on Medicare Supplement (Medigap) plans, Medicare Advantage plans (Part C), and standalone Prescription Drug Plans (Part D) to help you find coverage that fits your needs and budget. Whether you’re turning 65, retiring, or becoming eligible for Medicare for another reason, our team can walk you through your options and next steps with confidence.

Explore Medicare Coverage Options