Our Story
Hillock Insurance Group is a locally owned, full service independent agency dedicated to doing what’s best for clients. Carrying on the values of this community-owned business since 1999, Hillock Insurance protects individuals, families, and businesses. By offering all forms of health and life, property, and casualty insurance, we pride ourselves on making it simple and convenient to find affordable insurance that meets our clients’ diverse needs.
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Hillock Insurance was founded by Kathleen and Leroy Bennett as "Bennett Insurance" in 1999. Hailie and Jared Hillock purchased the agency in 2017 to carry on their legacy of care and compassion for insureds. Through several rebrands, two office locations, and broadly expanding our list of carriers, our core has always stayed the same: To bring excellent service to the community we love.


An Homage to the Mountains
Owner, Hailie Hillock, has spent her entire life in Wallowa County and has grown a passion for exploring the majesty of the surrounding mountains. The mountain featured, Sacajawea Peak, not only reflects that, but also the value and strength of community. Unexpected times and occurrences require support and it means a world of a difference to be able to reach out to someone close, someone you know, and someone that understands where you are coming from.
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Sacajawea Peak's namesake was a Lemhi Shoshone woman who, at 16, helped the Lewis & Clark expedition as a guide and interpreter through their journey. The Hillock Insurance team helps clients navigate too: from determining the best protection to helping as guides through challenging times.
Our logo reflects the beauty of our Wallowa Mountains and our promise to you. It's an honor to be trusted with supporting the most important areas of our community's lives.
Meet Our Team
Dedication. Expertise. Compassion.
Our agents are dedicated to doing what's best for you. Bringing expertise in a variety of insurance products from personal and business to life and health, it's our pleasure to help you find coverage that protects without breaking the bank.
Let's Work Together
541-426-4208
209 Hwy 82 Enterprise, OR 97828
Mon - Thur
Friday
9:00 AM - 4:30 PM
9:00 AM - 3:00 PM