Across the Many Aspects of Your Life

We provide expert guidance and superior solutions to help preserve the milestones and navigate the complexities of your journey.

Strategic Advice. Comprehensive Plans. Personalized Service.

A Long-Term Partner

Helping You Make Smart Risk Management Decisions Throughout Your Life

As your life evolves and successes add up one by one, it becomes increasingly important to surround yourself with a team of trusted professionals to help you manage and protect what you are building. The Bailey Howes Insurance team would be honored to be part of this advisory group. Our goal is simple: to assist you in safeguarding your most valued assets and complex exposures with the commitment, care, and clarity that has been applied to every other area of your financial life.

Personalized Risk Management and Insurance Strategies

Access the proactive advice, exceptional service, and superior solutions you deserve—and that a lifetime of accomplishments requires.

Consult

Our Professional Advisory Team

We craft risk management and insurance strategies that cover your whole life—not just one piece of it. This is a collaborative effort that involves giving careful attention to every detail, from your family and lifestyle to your assets and long-term goals. We believe this is the best way to design a comprehensive program that helps you confidently manage life’s risks and safeguard its rewards.

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Experience

Our Holistic Approach

At Bailey Howes Insurance, we are committed to providing you with an experience that feels different from the very beginning. We know your time is valuable, so we have made the insurance process as thorough yet simple and seamless as possible. From our initial discovery of your complete life, assets, and risks to our ongoing role as your risk management advisor, you will feel supported, confident, and empowered in every insurance decision you make.

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Explore

Our Specialties & Solutions

From your exceptional homes and luxury collections to your investment properties and business assets, your life is full of personal and professional successes. To protect what you have worked so hard to achieve requires not only a broad mix of insurance products but also regular assessments of these risk management solutions to make sure they evolve with your changing needs and potential exposures. This is our specialty at Bailey Howes: evaluating, planning, and coordinating a complete asset protection plan with exceptional and customizable services and solutions.

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Image of a beautiful New England style home

Hear From Our Clients

What Makes the Bailey Howes Insurance Experience Different?

    
 
 
       Posted on Google  
   
   Lee-Ann Norman 
 8 September 2025
 
 
 Trustindex verifies that the original source of the review is Google. Catherine Washington is excellent to work with!  She has helped me with my personal insurance questions as well as preparing to open a business questions.
  
 
      Posted on Google  
   
   Anders Beer 
 26 August 2025
 
 
 Trustindex verifies that the original source of the review is Google. I have had nothing but good experiences with Howes insurance group. Greg Howes, Traci Madigan, and Mike Umano were all really responsive and articulate when it came to finding the right insurance and answering questions regarding home, umbrella, and auto policies.

I have had plenty of questions for all of the people I named, and every one of them has been really insightful and articulate. Most recently I asked about those consumer insurance policies that are often sold by retailers and what differentiates them from the coverage under our homeowners policy. Mike was kind enough to go into detail about it and I really appreciated his objective breakdown on how the coverage works.

Keep up the fine work, Howes Insurance Group :)
  
 
      Posted on Google  
   
   Robert Stemple 
 18 August 2025
 
 
 Trustindex verifies that the original source of the review is Google. Over 30 years of helpful, quick answers. They treat you as friends not customers😀👍👍👍
  
 
      Posted on Google  
   
   Roger Beatty 
 4 December 2024
 
 
 Trustindex verifies that the original source of the review is Google. Howes is a small agency staffed with highly knowledgeable insurance professionals -- they're large enough to attract and retain experienced pros, and small enough to ensure personal contact in all business interactions. No voice mail maze, no call center, no chatbots -- they'll answer the phone directly, or call you back same day. When I call, I usually reach somebody I already know on my first attempt. I've been with them for years, and they've always done a great job.
  
 
      Posted on Google  
   
   Irwin Hipsman 
 26 November 2024
 
 
 Trustindex verifies that the original source of the review is Google. We have both our home and auto with Howes Insurance. Recently, we had a very challenging purchase of an auto and damage to our house. In both situations they were incredibly helpful and reassuring. Highly recommend the team and a special shout out to Traci.
  
 
      Posted on Google  
   
   Gregory Ladd 
 30 October 2024
 
 
 Trustindex verifies that the original source of the review is Google. The personalized service and breath of offerings really makes a difference!
  
 
      Posted on Google  
   
   Steve Neff 
 3 October 2024
 
 
 Trustindex verifies that the original source of the review is Google. The Howes team has been a valued services and support team. They are knowledgeable, proactive and we have a comprehensive umbrella policy for multiple properties, cars etc. Also a big shout out to our Account Manager Jennifer Drasser.
  
 
      Posted on Google  
   
   Jack 
 23 September 2024
 
 
 Trustindex verifies that the original source of the review is Google. From the moment I placed a call to Greg Howes, I knew I was in good hands. He took the time to explain every detail of the half dozen properties and autos I wanted to insure and came in less than other quotes at a higher level of coverage! Jennifer continued the process with countless phone conversations and emails. She's knowledgeable, patient, helpful, empathetic, experienced and extremely affable. I can't say enough and am grateful to have found Howes Insurance Group. You will be too!
  
 
      Posted on Google  
   
   Sylvia Diaz 
 6 September 2024
 
 
 Trustindex verifies that the original source of the review is Google. It's' a comfort for me to know that I have The Howe's Insurance Group behind me to help me navigate the complex business of insurance.

The Howe's Insurance Group is very responsive to my questions and needs. Together, we review, my family's insurance needs every year.