Day Insurance began its presence in St. Stephen in 1874. J. T Whitlock established a general insurance agency on Milltown Blvd. His son, William T. Whitlock, would take over the business when he passed.
In 1922, Guy R. Day joined Whitlock and together they renamed the business Day & Whitlock. Whitlock’s retirement in 1941 allowed Guy’s son Raymond to join the family business. This new era saw the business renamed again to Guy R. Day & Son Ltd.
In the 1960’s, the Day family moved the business to it’s location at 27 King Street; a home the business would have for more than 50 years.
At this time, the business had many irons in the fire as they sold insurance, real estate, and travel packages.
When Guy passed in 1971, Tim Eagan became partners with Raymond. In 1981, Daryl Spires and Raymond’s daughter, Lorraine Richard, also joined the family. In 1989, Tim and Daryl purchased the business from the Days, and Lorraine became a shareholder.
In 2002 the travel portion of the business was sold to St. Stephen local Crystal Burgess and became Maritime Travel; currently located on Milltown Blvd.
In 2006, Guy R Day & Son Ltd. purchased the Exit Realty franchise for this area and created Exit Realty Charlotte County.
In 2008, Daryl and his wife Chris purchased the remaining shares of the business, and brought in Brandon McGee as Sales Manager.
In 2014 and 15 Daryl and Chris purchased Max Hayre Insurance (previously on Carleton Street) and Olmstead Insurance (previously on Milltown Blvd). With the added clients and 3 additional brokers, the business was becoming too big for 27 King.
In 2016 Guy R. Day & Son Ltd., now operating as Day Insurance, moved to its current location at 78 Milltown Blvd; the Clark building. The new location boasts waterfront views, better accessibility, and ample space for brokers and real estate agents alike.
Day Insurance was founded on the principles of fair and honest business practices, and has promoted that ideology in the area for more than 140 years. The business remains a staple in the community.