Starting September 11th, our offices will close at 4 PM on Fridays.
We’re your neighbors, helping you protect what you love
Planning for the future can feel uncertain, but protecting what matters most shouldn’t be. With Ashland Insurance, you can have peace of mind knowing that you’re covered in all the important areas of your life.
Whether it’s your home, business, income, or health, we’re here to provide the right insurance to safeguard your future and well being of your loved ones.
As a veteran-owned, local agency serving the community since 1981, we’re committed to delivering personalized coverage – both personal and commercial – designed to fit your needs, no matter the size of your concern.
When life takes an unexpected turn, you can count on us to be there.
Contact us today for a no-obligation insurance consultation: 541-482-0831 or 541-857-0679
Areas of Insurance We Cover
Personal insurance coverages protect your most valuable assets—your home, your vehicles, and most importantly, your income.
Businesses need a wide variety of insurance coverages. Almost every business requires property insurance to protect its assets.
The Affordable Care Act health insurance reform law requires most people, including children, to have health coverages or pay a penalty.
Develop your retirement plan strategy, and keep your heirs' interests at heart.
Superior Customer Service
It's more than just a slogan, it’s our promise.
Rick S
I have been more than satisfied with great customer service for nearly a decade. In both business and for my personal insurance needs, I know where I stand because they take the time to make sure I understand. Even better, when we transferred our business insurance, we saved 40% per year for better coverage. I can easily recommend Ashland Insurance to anyone.
Garrett K
I have worked with Ashland Insurance for six years now. The whole team is top-notch and very knowledgeable. I highly recommend them in their areas of expertise including property and casualty as well as life insurance.
Crystal R
I switched my home owners' insurance to Ashland Insurance because their price was better than I could find anywhere else and the service was excellent. They were persistent when mortgage company kept losing the paperwork. They took care of me and made sure nothing was missed. I highly recommend Russ S. & all the folks at AI!
Emily T
I am a HUGE FAN of Matthew Shilts and Russ Schweikert. They are absolutely the BEST when it comes to insurance. Excellent customer care and prices. I highly recommend.
Lauren T
I have worked with several of the agents at Ashland Insurance including Matthew Shilts and Russ Schweickert, Sue Carney as well as Lori Grigsby. All have been helpful, honest and I have felt very cared for. Matthew has gotten me such competitive rates on my auto and he is very easy and professional to work with. Russ has helped my family with our complex life insurance needs and Sue and Lori make sure that we are taken care of with our healthcare coverage. I love having all of my insurance at one location with agents I can trust. Thank you Ashland Insurance for your level of customer service and integrity.
Colbee M
I am very grateful for the folks at Ashland Insurance. Everyone there has been so friendly and helpful. After reviewing my auto and home policies they were able to give me better coverage at a third of the price. It doesn't get much better than that!
Sabrah M
Russ Schweikert and Matt Shilts have been so helpful for me and my business. Not only did they inform me of the insurance I needed, but found the best rate and the perfect fit for me. Matt has been an ongoing resource as questions come up as well, which I really appreciate. I highly recommend Ashland Insurance to anyone needing help navigating the insurance offerings and what they need to be protected.
Teri B
I have worked with several agents in this office - Russ Swikert, Matthew Shilts, and Sue Carney. My experience with all of them has been pretty awesome. Each one has gone above and beyond for me, and demonstrated their high level of knowledge and commitment. I highly recommend Ashland Insurance for any insurance needs you may have. They work with many companies to find you the right coverage and something that will work for your budget.
Robynne W
Matt Shilts at Ashland Insurance is knowledgeable and responsive. He does homeowners, renters, and commercial coverage, and will review your coverage to see if he can save you money. If he can't do better, he'll tell you. And if he doesn't have the type of coverage you need, he'll refer you to someone who can help. It's that kind of customer service and integrity that makes Matt my go-to insurance guy!He's licensed in California, too!
Joel D
Ashland Insurance is the one-stop-shop in Jackson county for Auto, Home, Life, and even Business! Many of my friends and clients have been impressed with the level of service, attention, and creative solutions they’ve experienced working with this group of professionals.
Anna D
Great group of professionals. I recommend them to my friends and family all the time.
Josh M
Very helpful staff and friendly environment.
Ericka P
Tom was a great help!
Steven S
Great pricing, exceptional service! A winning combination!
Jeffrey N
I have been using Ashland Insurance for five years now, for my home, auto, and motorcycles. They have been great! I called my agent and told him I was buying a motorcycle - by the time I had finished the paperwork and paid the seller, I was insured on the bike! Fantastic service, amazing low prices.
Ellen S
First of all, I'm biased because this is my dad's company. BUT this gives me a lot of insight into how they operate and I can share some of that with you!- This is actually a family-owned company. The Wilson's have owned Ashland Insurance for decades and while they are retired, their sons and my dad continue their legacy and love what they do. - They are happy to quote your Insurance and if you can get it cheaper somewhere else, they tell you. - They explain the full benefits of insurance with them and if you're missing something on your current insurance and need to switch, they tell you why and how to get the best price for the most coverage. - They are actually licensed in many states all over the country, so you can get amazing insurance even if you have business/homes in multiple states. This is unusual for a small Family-owned company! - They are much more concerned with amazing follow-up and treating their employees well than with trends or fads. They have over a dozen employees but it is not unusual for them to stay for decades!I highly recommend them not just because they're family, but because they do a really amazing job.
Jeff B
“I am extremely impressed with the service my wife and I received from Tom Wilson at Ashland insurance. We sought out his advice regarding new health insurance policies. Tom helped us to navigate through the maze of options, and find a policy that was within our family budget and fit our needs. Having his help made all the difference in the world!”Ashland, OR
Scott P
“Matt Shilts totally takes the effort and stress out of the insurance process. He's a pro and will find you the best fit with ease. I personally use his services and have never felt so confident in the process.”Ashland, OR
Ben W
“Russ Schweikert and Matt Shilts have been so helpful for me and my business. Not only did they inform me of the insurance I needed, but found the best rate and the perfect fit for me. Matt has been an ongoing resource as questions come up as well, which I really appreciate. I highly recommend Ashland Insurance to anyone needing help navigating the insurance offerings and what they need to be protected.”Medford, OR
Ashland Insurance is Committed to Community
We’re your neighbors, helping you protect what you love.
When Ashland Insurance was founded in Ashland, Oregon, in 1981, the Wilsons knew that connecting with their friends and neighbors would be the best way to grow their small-town insurance business. Nearly four decades later, their legacy continues—we’re still locally owned, and we’re invested in our community and committed to making a positive impact.
Community Organizations We Support
When life doesn’t go as planned, we’re here for you. Our customized personal, business, retirement planning, health, and life insurance coverage keeps you protected.
Community Organizations We Support
We build long-term relationships with our clients. Whether you’re seeking medical, home, or auto insurance coverages for the family, a business policy to secure your assets, or researching life insurance to match your financial goals, we’re here to make the process painless. We represent over 200 companies.
Insurance? We’ve Got You Covered
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Business
Health & Life
Pet
Current Information
Black Bears Are In Ashland: What We Can Learn From Fat Bear Week
I know, I know, it’s a lot to unpack here, but don’t stress, because we’ve got you covered. First off, Yay! It’s Fat Bear Week! We get to learn about (and laugh at) some extra chunky ursids. Second, Oh no…there are black bears in my backyard? Black bears have been spotted in Ashland, and not […]
Celebrating Autumn: Discover the Magic of the Fall Harvest Festival
Can you feel it? The air is starting to cool down, days are getting shorter, and now when you catch that whiff of smoke on the breeze, it smells like fireplaces warming homes instead of the wildfires evacuating them (if you’re from the area, you know what I mean). That’s right, we’re entering autumn, and […]
Wine Crush: 3 Essential Strategies to Secure America’s #1 Wine Region During Harvest Season
Picture this: It is two in the morning, the de-stemmers are roaring, and the most important wine crush of your career is in full swing. The bins are overflowing with premium Syrah, and in just a few short days, your entire year’s revenue will be sitting inside those active fermentation tanks. The energy is electric, […]