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MiddleOak Specialty®, in partnership with the finest independent agencies in your community, helps provide the financial security and peace of mind that you want and should expect from an insurance company. Our distinctive specialty coverages for personal and commercial protection are crafted with you in mind. From the Worlds Apart® coverage for a professional property owner, to protecting your Yacht or Vacation Income Property, MiddleOak Specialty® provides the detail, experience and protection that you want.

MiddleOak Specialty® has the financial strength and resources of one of the nation’s fifty largest property-casualty companies* which holds an A+ (Superior) financial rating from A.M. Best. This allows our agents and customers to feel financially secure with their insurance decision while still enjoying the convenience and strong relationships that come from working with a local agent.
Our commitment to serving our customers through the Independent Agency System results in strong personal and professional relationships that deliver the ultimate in value to policyholders. Find an Agent near you now !


* A member of the COUNTRY® Financial group

We are pleased to introduce our new Brand Name, MiddleOak®. While much has changed over the decades, the core values of our founding companies—Middlesex Mutual Assurance Company and Holyoke Mutual Insurance Company in Salem—have not. Our dedication to doing things right, to working with the “best of the best” independent agents, to innovation and strength through underwriting, our quest for market leadership, and to providing policyowners with the highest value and quality in insurance protection still guides our actions everyday.

To learn more about our Insurance Programs and the independent agents who offer them, please select the State in which you reside from the State Choice selection (upper right).


MiddleOak Specialty® on the move

MiddleOak Specialty® has introduced two new insurance programs in selected states. CAPsure is a comprehensive program for condominium associations offering protection for commercial property and liability exposures "VIP" is a program for vacation income properties. Please call 800-225-2533 Ext. 2211 for further information.


Policies issued by Holyoke Mutual Insurance Company in Salem - Salem, MA and Middlesex Mutual Assurance Company - Middletown, CT
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