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Westfield Insurance, the primary subsidiary of Westfield Group, is a multi-line provider of business property & liability insurance, personal lines insurance (including auto, homeowner's and specialty), agribusiness insurance, and surety bonds. Based in Westfield Center, Ohio, Westfield employs over 2,400 nationwide including 1,700 in their home office. Despite its rural location, it is the largest employer in rapidly-growing Medina County.

Westfield began as Ohio Farmers Insurance Company in 1848, when a group of farmers joined forces to insure their properties. In 2010, the company collected $1.4 billion in premiums. At the helm are Bob Joyce, Executive Chair of Westfield Group, Jim Clay, CEO of Westfield Group, and Ed Largent, President of Westfield Insurance.

Westfield's products are distributed through a network of more than 1,200 independent insurance agents, and now the company has grown to become one of the top 50 property-casualty insurers in the U.S. It is also one of the nation's top-ten providers of farm insurance.

In addition to providing insurance and financial services, Westfield owns the Westfield Group Country Club, a 36-hole championship golf course which hosted the Junior PGA Championship until 2007. Also on company grounds are the Blair Center (a convention center), Westfield Bank, and Westfield Inn, a newly-renovated private hotel. The Home Office, Country Club, Blair Center, Bank, and Inn are all situated in the heart of the small Village of Westfield Center. The Colonial & New England architecture of the company buildings lends a distinct appearance to the town square.

Westfield Insurance also sponsors seven televised High School Scholastic Competitions including the Brain Game, Academic Challenge, Hometown High-Q, In the Know, Quizbusters and BrainBusters.