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Bossola's Insurance - Insuring Cheswick and All of Pennsylvania

Bossola’s Insurance Agency has been serving the Alle-Kiski Valley since 1942. It is the oldest business in Cheswick. We are a family owned and operated business now owned by Robert Tomayko the 3rd generation to own Bossola’s Insurance. Agents include Robert Tomayko with 34 years experience, my aunt Dorothy Tomayko with 41 years experience, and my daughter Nicole Tomayko (who is the 4th generation) with 4 years experience as of 2018. We specialize in Auto, Home, Life, and Commercial Insurance.

At Bossola’s Insurance you are always welcome to come in to make your payments or file a claim in person, or just stop in to say hello. We even have some clients who like to stop in just to hear or tell a new joke. Bottom line we are a family owned and operated business and your family is extremely important to us.

Specializing In Erie Insurance

Erie Insurance has been helping customers since 1925 with their auto, home, business, and life insurance needs.
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Robert Tomayko
Robert Tomayko
President
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Auto Insurance

Paying too much for auto insurance? With our flexible coverage options and expert service, you’ll know that your vehicle is getting the best protection possible.
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Home Insurance

Your home is your greatest investment, but you shouldn’t have to break the bank to insure it. Find out how much we can save you on your policy.
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Business Insurance

As a business owner, you have enough on your mind without having to worry about your insurance needs. Let us find the best coverage at the best rates for you.
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Recent News & Updates

Home & Auto Spring Maintenance Checklist

Posted: March 16, 2026

Spring maintenance keeps your property in good condition and helps you get better insurance rates. Evaluating your home exterior after winter is a critical step in identifying minor problems before they turn into major structural damage. You must prioritize inspecting your roof, cleaning out gutters, and checking proper soil drainage. Confirming your sump pump works correctly will further reduce your risk profile. Factors that affect...

Beyond the Workplace: Extending Group Benefits to Families

Posted: March 13, 2026

Many companies find that offering family coverage drives employee retention. It reduces costs from frequent turnover. Employees stay loyal when employer-sponsored plans protect their spouses and children. This stability helps maintain a positive workplace culture. It ensures institutional knowledge stays within the company. Investing in the health of an entire household strengthens the business. Resources show that the organization values people beyond professional contributions. This...

Hydroplaning: What is It and How Can You Avoid It?

Posted: March 9, 2026

It doesn’t matter the season: heavy rain and wet roads can occur at any time of the year. That means slick roads, limited visibility and yes, hydroplaning. No matter the weather, having the right auto insurance can give you peace of mind. But hydroplaning can be scary – so it’s important to understand the conditions when it’s likely to occur, and what to do if it...

Key Questions for Your Business Insurance Renewal

Posted: March 4, 2026

Your upcoming policy renewal constitutes a crucial business risk checkup rather than just another administrative bill to pay. As your company grows and evolves over the next 12 months, your baseline exposure to operational risks naturally shifts in parallel. Expanding operations by adding new locations, purchasing upgraded equipment, launching new services, or hiring extra staff significantly changes your specific liability profile. Factors that affect the...