InsuringThe ShoreSince 1959

Welcome to Riddleberger Insurance. We've updated our name but are still the longest-running insurance agency on the Eastern Shore and remain dedicated to serving you and your family, just like we have since 1959.

60 Years As A Proud Member Of The Eastern Shore Community

Like you, we've made our home here and our roots grow deep. You'll see us in the grocery store, at Friday night football games, enjoying a day at the beach or out for an afternoon cruise on the water.

As a service to our neighbors we have expanded our insurance carriers and offerings which means you now have even more options to secure the best rate and coverage you need.

Family Holding Hands


Your home shelters what matters most to you - your family. Make sure it's always protected with our range of residential coverage options.

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Commercial Building


Make sure your business can support you for years to come. Get the insurance coverage you need.

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From your livestock and crops to your equipment and structures, we have the insurance options to ensure your future is protected.

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What Our Neighbors Say About Us

"Friendly, Helpful, Considerate."

Rhoder Goldborough

"Even with the vast array of local, TV, internet competitors, we have never considered leaving Riddleberger insurance. For over 20 years , our agent Brenda Wroten has provided us with accurate efficiently delivered advice and information about insurance coverage for our home, vehicles, and barn. She has earned our trust and respect. Thanks Brenda!"

Ed & Bonnie Baker

"I am extremely happy with the work that Riddleberger Insurance has done for me and my family over the years and hope I have many more years with you. The staff there are very kind and helpful and I am happy with their service. "

Jackie Cheezum

"I like coming into the Agency to see their smiling faces!"

Ethel Smith

"I have personally and professionally known Lisa Balderson for over 30 years. She has facilitated with my auto, home, business and life insurance policies. Lisa’s vast knowledge of the complicated, ever changing insurance industry, has guided me throughout the years. Her knowledge and advisement has allowed me to confidently make important decisions. My family has experienced accidents and losses, including a chimney fire. Through each claim, Lisa made the process go quickly and smoothly. Her commitment and dedication to her clients are unsurpassed. Over the years, I have compared insurance rates. Nationwide Insurance rates are competitive. However, nothing compares to the customer service and “one on one” communications that I have with Lisa and the staff at Nationwide Insurance. "

Elizabeth Luckett

"I have worked with Julie for over 10 years with all of my insurance. She is always pleasant and professional to work with, and treats me like I am the most important customer. She always answers my questions in a timely fashion, suggests new products, and ways to save me money. I would highly recommend Julie and Riddleberger Insurance."

Ms. Suzanne P. Jefferson

"I have used Riddleberger Insurance for over 20 years. I have never been dissatisfied even once. They are professional, knowledgeable and friendly. Riddleberger Insurance has made life easy whether explaining my options or making claims. They’ve had my family’s back in every circumstance and made us feel like they work solely for us. Loyalty like they provide is hard to find now a days. "

Jody and Tracy Ward

"Brenda Wroten has always be on top of things when it comes to insurance. Same day quote , need to know about adding on to an existing policy no problem same day answers. I always ask for Brenda when I call with insurance questions about my rentals."

Charlie Thomas

"There are a lot of overwhelming tasks that come with buying a new house. I thought changing our homeowners insurance would be one of them. Not thrilled with the provider we were using we decided to contact Jennifer at Riddleberger Insurance. She made getting a new homeowners insurance policy easy. She was wonderful to work with and even reviewed our other policies and was able to bundle our other insurances to save us additional money. She was knowledgeable, thorough, and seamlessly got all our existing policies switched over very quickly. It was a pleasure working with her and even better she made what I thought would be a daunting task very pleasant. We highly recommend Riddleberger Insurance and Jennifer for all your insurance needs."

Amy Slowe

"Cindy has always been reliable and pro-active in seeking out the best type and amount of insurance coverage for our business. She is dependable and very responsive when we have questions or concerns. It is always reassuring to know she is constantly looking for ways to improve our coverage and business relationship."

Michele Towers Bodine

Towers Concrete Products, Inc.

"My insurance needs are always met, thanks to the great work by my insurance manager Sandy Higdon, She is very easy to get a hold of any time, great working with them."

John Coursey

Owner of John W. Coursey and Son, building contractor

"Shannon, thanks for all your efforts in acquiring the best coverage for my insurance needs. You are truly an asset to Riddleberger Insurance."

Dennis Lanham

" The Chestertown office is the BEST!!! The ladies in the office are very nice and efficient. When you call in they are always there to help you whatever your needs are. Also would like to Thank Lisa for her friendly reminders about your insurance payments."

Laura Brilz

"For the past 30 years, I have known Lisa B through our time working together as our Nationwide Insurance agent. Lisa is a hard working friendly and dedicated individual. Every task Lisa takes on is done to perfection handling our many different insurance policies (farm, house, vehicles and commercial). I have been able to ask her many question and seek advice. Lisa has become a major player in our family. "Just hearing Lisa's voice brings me comfort, before we get down to insurance business". It is true Lisa B is always on our side."

Joyce Biddle

"Always friendly smiles and good service. They are willing to let me know where I can save money and gives me good advice. "

William Robare

"Dealt with many insurance companies in the past but don’t ever plan to leave Riddleberger insurance! Sandy always provides exceptional customer service, always quick to respond, and treats you like you are her only customer! "

Lori Bishop

Rock Creek line Construction

"I have been a customer for ten years and will continue to work with Sandy Higdon and the team at Riddleberger insurance because they value their customers. I can call Sandy anytime day, night, weekend, or holiday and get any help I need which is extremely important for a full time working mother of three small children 5 and under who knows very little about insurance. She reminds me when payments are due, sets up automatic payments and gives honest recommendations for what policies to carry and go without. I trust Sandy and Matt. "

Kasey Royer

The Insurance Freedom You Need

In order to provide the best insurance options for the Eastern Shore, we’ve become an insurance broker. That means instead of just selling one insurance brand, we can now search a variety of insurance carriers to find the best option for your specific needs.

To us, this means we can give you the best insurance coverage for your home, business or farm, all on a budget that fits your needs.

We've spent the past 60 years earning your trust, taking care of you and we're looking forward to providing good ol' insurance coverage for the good folks who've made this community strong and prosperous. We're focused on giving a century of service to our community.

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We Help Protect What Matters


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Let's Talk About Your Insurance Options

Choosing the right insurance can be tricky but we are here to help! Click the button below, tell us a little bit about yourself and which insurance options you would like to see.

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