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

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 Supplements

Whether you’re setting the world on fire in your 20s, saving large in your 40s and 50s or settling into your 70s, 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.

How We Invest in Your Future
Auto Insurance
Home Insurance
Business Insurance
Life & Disability Insurance
Medicare Supplements