About Stonewall Insurance Group

Stonewall Insurance Group is an insurance agency based in New England that focuses on getting their customers the best coverage for the best price. Nowadays, customer service seems to have become a thing of the past for many businesses, especially in the insurance industry. At Stonewall Insurance Group, our main priority is providing excellent customer service while getting you the best coverage possible.

The best customer service, the best coverage, the best price

We’ll take care of your insurance, so you can focus on what’s important.

Our History

Back in 1988, Jeff DeMarey was helping out his father’s insurance agency when he saw a pattern of big box stores putting small mom-and-pop shops out of business. He watched as companies like CVS, and Home Depot took out their local competitors and he realized it was only a matter of time before the same was done in insurance. In hopes of fighting this, he started looking for a niche to specialize in and naturally, he landed on classic and collector car insurance. Over the next 15-20 years, he was able to grow the agency to over 3,500 policies, finding new ways to automate and streamline the insurance process.

In 2008, he decided to branch out and start Stonewall Insurance Group. Still specializing in classic and collector cars, Stonewall is now able to write insurance for everything you own, in any of the 50 states. 

About Stonewall Insurance Group

Years of Combined Experience

Largest Hagerty Top Gear Agency

Different Insurance Companies

Why Stonewall Insurance Group?

We're on your side

Being that we are an independent insurance agency, we are able to work with the top insurance companies without being tied to one. This means that we can shop around to find you the best coverage for the best price. If a better deal comes up later on, we’ll notify you so you never miss out.

Service with a smile

Over the years, customer service has gotten worse and worse, especially in the insurance industry. At Stonewall Insurance Group, customer service is our top priority, so we always go the extra mile no matter the size of your policy.

Custom Policies

A one-size-fits-all policy really doesn’t fit anyone. That’s why we tailor each and every policy to your specific needs. We’ll make sure you’re adequately covered and not paying for things you don’t need.

Experience you can trust

Throughout our 75+ years of experience, we’ve seen it all so know what coverages you need to stay safe based on your situation. Other agents might try to cut corners and reduce your coverage to make your policy seem cheaper, but it might cost you far more in the long run. 

One-Stop Shop

Stonewall Insurance Group was built to be a one-stop shop for all of your insurance needs. We can insure all of your Vehicles, Businesses, Properties, and more. The best part is that when you bundle your policies with us, we can save you up to 25%

Our Customers

Read some of our reviews or ask any of our customers about us to see why 99.25% of our customers choose to stay with Stonewall Insurance Group every single day.

Meet the Team

Jeff DeMarey, President of Stonewall Insurance Group

Jeff DeMarey


Jeff started his insurance career in the late 1980s working with his father. Shortly after, he took over the business and started specializing in insuring classic cars.

Outside of working in insurance, he is truly passionate about the automotive world. He currently serves on the National Board of Directors for the Classic Car Club of America, where he has been heavily involved for many years. He also serves as a judge at some of the most prestigious auto events in the country, such as The Amelia and Greenwich Concours d’Elegance. He has recently started the Springfield to Boston Education Foundation, a charity foundation to help educate children about the world of classic and collector cars.

First Car: 1968 Ford Mustang GT Fastback

Call Jeff at (413) 566-0091, Ext. 30

Jeff DeMarey, President of Stonewall Insurance Group

Lori Sheehan

V.P. Personal Lines

Lori started her career in the insurance industry in 1998, working for CNA Insurance. Encompass soon acquired CNA, and she continued to work there for another 17 years as an underwriter and customer service representative. With her years of experience working as an underwriter, her knowledge of all personal lines products, including automobile, homeowners, and umbrella insurance, is unparalleled.

Outside of working in insurance, Lori has always loved fast cars and any sort of American muscle. She has owned a variety of fun cars from a 1980 Chevy Chevette to a Ford Ranger with a 5.0 mustang engine in it, outfitted for racing.

Fav Car Owned: 1989 Shelby Shadow CSX

Call Lori at (413) 566-0091, Ext. 33

Jeff DeMarey, President of Stonewall Insurance Group

Alyson Reed

V.P. Commercial Lines

Alyson started her career in the insurance industry in the late 1980s working in commercial insurance for several large agencies in the Western Ma and Worcester areas. She also spent time as a national broker and salesperson for some of these agencies. After knowing Jeff for over 20 years, she agreed to direct the commercial division of Stonewall Insurance in the fall of 2019.

Alyson specializes in finding businesses the insurance they need. Many classic car restoration shops or clubs have never been properly insured until Alyson fought for them.

First Car: 1972 Chevy Nova

Call Alyson at (413) 566-0091, Ext. 35

Chris DeMarey, Marketing Manager for Stonewall Insurance Group

Chris DeMarey

Marketing Manager

Chris is a recent graduate of Bryant University, with a  major in Marketing and Applied Analytics. Noticing the help his father needed in the marketing side of Stonewall Insurance Group, in the fall of 2022, he offered to help get it on track. Since then he has been working on web design, search engine optimization, organic traffic generation, social media content, paid advertising, and more. 

Outside of Stonewall Insurance Group, Chris is also heavily involved in the automotive world. He is on the Board of Advisors for the New England Region of the Classic Car Club of America and is a judge at some of the most prestigious car shows in the country, such as The Amelia and Greenwich Concours d’Elegance. 

Fav Car Owned: 2012 Jeep Grand Cherokee SRT8

Call Chris at (413) 454-7600

Shawn Jones, V.P. of I.T. for Stonewall Insurance Group

Shawn Jones

I.T. Director

Shawn has been in the I.T. industry since 1989. Beginning his career as a programmer, he has since moved on to databases, email, virtual servers, and many others. In his time in I.T., Shawn has worked for companies like Hanes, OPTUM, and the National Crop Insurance Services.

Knowing Jeff for many years beforehand, Shawn has been at Stonewall since the very beginning, in 2008. He has set up all of the computers, servers, software, backups, and security. He is continuously learning new programs and software to keep Stonewall Insurance Group safe, and running smoothly.

Fav Car Owned: 1991 Firebird Formula

Call Shawn at (413) 566-0091, Ext. 36

Our Affiliations

AIG Insurance

American International Group, Inc. (AIG) is a leading international insurance organization serving customers in more than 130 countries and jurisdictions. AIG companies serve commercial, institutional, and individual customers through one of the most extensive worldwide property-casualty networks of any insurer. In addition, AIG companies are leading providers of life insurance and retirement services in the United States.

Travelers Insurance

In an uncertain world, Travelers is an insurance leader, committed to keeping pace with the ever-changing needs of our customers, and anticipating their needs for the future. There is no stronger testament to our dedication to protecting customers from loss than our continued innovation and ability to transform our industry.

Safety Insurance

Safety Insurance was founded in 1979 with a belief that we would succeed as a company if customers were given the best possible service. As we’ve grown and expanded our product line to include a full range of property and casualty insurance products, staying committed to that belief has meant even more.

Safeco – A Liberty Mutual Company

We know that trust matters when it comes to some of your biggest investments, like your home, car, and even your boat. From the smallest fender-bender to a storm-damaged home, we’re standing ready at life’s trying moments – here for you at any time, at any day of the week.

Chubb Insurance

If being treated fairly and paid quickly are important to you when you or your company has a property or casualty insurance loss, then you want Chubb. When you insure with Chubb, you’re buying real insurance.

For 130 years, the Chubb Group of Insurance Companies has been delivering exceptional property and casualty insurance products and services to businesses and individuals around the world.

Encompass Insurance

At Encompass, our focus is on personal insurance policies. We strive to provide a simpler insurance experience by offering protection for your homes, autos, powersports, jewelry, valuable collections and more under one package policy—The Encompass OneSM Policy—that comes with unparalleled customer service and superior hassle-free claim service.

Swyfft Insurance

Swyfft uses patented analytical methods and unique data sources to more accurately assess the risks to your home and property. In most cases, this enables us to provide a premium quote in a few seconds using just your address, and we can usually offer you a lower premium, too.

Usaig Insurance

For more than eight decades, we’ve been a leading provider of insurance to the aviation and aerospace industries. We’ve been there, time after time, to support the innovations that have pushed aviation to the next chapter.

Global Aviation Insurance

Global Aerospace is a leading provider of aircraft insurance and risk management solutions for the aviation and aerospace industries. Our over 95 years of aviation insurance experience enable us to develop customized insurance programs structured around the needs of our clients. 

AIG Aviation Insurance

For over 70 years, AIG has provided innovative aerospace insurance solutions for nearly every type of industry using aircraft, from agriculture to space. Our aviation professionals will work with you to customize coverage options that can help minimize risks and maximize safety – to help keep your operations aloft.

Hagerty Insurance

It’s all about passion. Over the last 25 years, we’ve grown to be the global leader for collector car and boat insurance. But we’re still just a family business built on love for the hobby. Our passion drives us to keep improving our product, and to keep giving our clients the best service imaginable.

American Collectors Insurance

American Collectors Insurance is a recognized leader and innovator in our industry. With over 30 years of experience, we provide affordable agreed value insurance for collectibles and collector vehicles. We strive to earn our customers’ repeat and referral business by employing professional, experienced personnel and cutting edge technology to provide the highest level of customer service.

Condon & Skelly Insurance

Since 1967, we have been helping our customers protect their classics with affordable, industry-leading insurance coverage. We’re a group of collectors, enthusiasts, and professionals who specialize in insuring all types of collector vehicles – from antiques and classics, to specialty and exotic cars.

American Modern Home Insurance

American Modern is a widely recognized, national leader in the specialty insurance business. With close to 50 years experience in the manufactured housing insurance sector, the company delivers specialized products and services for residential property and the recreational market. One of our newest lines is pet health insurance.

 Vault Insurance

Vault is made up of more than 100 smart, dynamic and driven professionals throughout the United States, each one of us ready to exceed agent and customer expectations every day. That’s what we do, because that’s who we are.

Infinity Insurance

At Infinity, we understand that great service to you is related to a great working environment for our team and that is why we establish goals and objectives for all employees that measure respect and teamwork in the workplace. In the end, Infinity creates an environment for team members to excel, which places us among industry leaders nationwide, so that they can continue to provide an ever-better experience for you.

Foremost Insurance

We’ve spent the last 60 years getting to know the markets we serve exceptionally well. We understand the coverages you are looking for with the specific types of policies you may want. We’ve taken what we learned and turned that expertise into a solid business.

Specialty Aviation Underwriters

Specialty Aviation Underwriters is the aviation underwriting company for Old United Casualty Company also d/b/a Vantage Casualty Company in the State of California. Located in Merriam, Kansas, Old United Casualty Company has an A.M. Best A rating

National Marine Underwriters

A leading underwriter of recreational boats/yachts and six passenger charter boats. Marine Insurance is all we offer. We have been successfully underwriting this class of business since 1983. Focusing on one class of insurance allows us to concentrate our efforts and provide a comprehensive all risk policy with competitive terms. Coverage is available in most states, with additional territorial extensions available.

Markel American Insurance

With 70+ years of experience, helping our customers find solutions for unique, unusual, and hard-to-place risks is what we do every day. Unmatched experience and knowledge of niche markets help us guide our customers and provide meaningful insurance solutions. Exceptional customer service has always set us apart. Selling a policy comes second to providing customers the guidance and support they need and deserve.

Progressive Insurance

The Progressive Group of Insurance Companies has always lived up to its name by being one step ahead of the insurance industry, and finding new and affordable insurance solutions. We began in 1937 with the first drive-in claims office, became the first to introduce reduced rates for low-risk drivers, and then changed the insurance shopping experience by offering comparison rates on the Web.

Starr Aviation Insurance

The size and complexity of today’s aviation marketplace is constantly changing, requiring new levels of risk management, innovative insurance solutions, and financial security. Starr Aviation is already there… meeting these needs for you and your business.

United Marine Underwriters

Boating, what a grand lifestyle, the vast waterways of the United States offer all boaters an excellent resource. Whether pleasure boating on the inland waterways, sport fishing off the Florida coast, or cruising in the Pacific, the rest of the world and its worries can seem a million miles away. United Marine Underwriters specializes in protecting this lifestyle. 

Have any questions? We're here to help

Contact us today to talk about getting your business the coverage it needs.