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Our independent insurance agency has years of experience in financial services.

About Our Agency - Young Man with Suit on Smiling and Standing with an Officer and Firefighter in Front of a Yellow Firetruck

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Let the professionals at our insurance agency help you forge the strongest shield possible to help you protect the things you are working hard to build.

Who we are.

We are an independent insurance agency specializing in a variety of insurance solutions to meet your needs. Established in 1979, we have served our clients throughout the Mid-Atlantic region for over 42 years. Landmark is committed to the highest ethical and business practice standards. Our team has a history of leadership in our industry, the business community, and the area we serve.

Our Mission

At Landmark Insurance & Financial Group, Inc., our mission is to help you. Protection, education, and integrity are the foundation of what we do. Utilizing the power of an independent agency, Landmark Insurance & Financial Group, Inc. is “Large Enough to Serve You, Small Enough to Care!™”


Years in Business

What makes us different.

Because we are independent, we work with a variety of top-rated companies to help you find insurance and financial solutions that work for your needs, and we are always looking for ways to use new technologies and innovations to serve you—in fact, our office was the first in town to have a fax machine back in the day. But more than that, we’re your neighbors. We protect businesses and people we know and care about, and that means we always look for ways to protect you better.

Doing More Than Just Insurance

We love to get involved with our community and local events, and we love to give back however we can. That’s one of the reasons we sponsor the Charles McClenahan Technical School Scholarship.

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Contact Landmark Insurance & Financial Group, Inc.

Our Princess Anne, MD Office

30386 Mt. Vernon Road
Princess Anne, MD 21853

 410-651-2110 local
 888-651-2111 toll-free
Email Us
 410-651-9288 fax

Our History


Landmark Insurance & Financial Group, Inc. was first established in 1979 by Charles McClenahan, aka Charlie Mac, in Crisfield, MD. Even as the business grew, Charlie, served his community as Mayor of Crisfield from 1978-1982 and then served as a Member of the House of Delegates for Somerset, Wicomico, and Worcester Counties from 1992-2003. As the business grew, Charlie Mac relocated to a more centralized location in Princess Anne, MD, where it remains today.


Charlie built a loyal and successful team around him, bringing in K. Jill Hall in 1995, and she grew the health, life, employee benefits, and financial planning departments of Landmark Insurance. “Jill,” as she is widely known and respected within the community, became part owner in 1997.


As time passed, both of Charlie’s children, Ryan and Heather came to work at Landmark, eventually taking on more responsibility as Charlie prepared to retire. When Charlie Mac retired in 2014, Jill took over as president and CEO, with Ryan and Heather stepping into vice president and managerial roles.


Charlie Mac passed away in 2017 at the age of 76; however, his legacy still lives on, with Landmark Insurance just celebrating its 40th anniversary in August 2019.

Personalized Solutions

Get the power of choice with insurance that’s designed for your unique needs.

Knowledgeable Service

We’ll be there for you with reliable service and support to help you make informed decisions.

Trusted Relationships

You can rely on us to simplify the insurance process and advise you on your insurance.

Landmark Insurance & Financial Group, Inc. is located in Princess Anne, MD, and licensed to serve clients throughout Maryland and several other states.

Let’s Get Started

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  2. Step 2Review your options with us.
  3. Step 3Get the coverage you need.

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