​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. ​

---