From an 1888 mutual insurer to a 1960s IT shop — a look at the Chatham-Kent businesses with the longest documented operating histories in 100CK's directory.
These are the Chatham-Kent businesses with the longest continuously documented operating histories in 100CK's own directory — sourced from each business's own published company history, not survey estimates. This isn't a comprehensive census of every long-running business in the municipality; it reflects founding years we've been able to confirm so far. See the Business Index for the full, live count.
Kent & Essex Mutual Insurance — founded 1888
Kent & Essex Mutual Insurance holds the oldest confirmed founding date in 100CK's directory, providing farm, home, auto, and commercial coverage across Chatham-Kent and Essex for well over a century.
Maple Mutual Insurance — founded 1910
Maple Mutual Insurance, headquartered in Dresden, has served agricultural and rural communities in the area since 1910.
Capitol Theatre — founded 1930
The Capitol Theatre opened in downtown Chatham in 1930 as a movie palace. Restored and now operated by Chatham-Kent Arts + Culture, the 1,210-seat venue hosts more than 100 concerts, live theatre, comedy, and film performances a year.
Summit Roofing & Sheet Metal — founded 1948
Summit Roofing & Sheet Metal has provided roofing and sheet metal services out of Blenheim since 1948.
Simpson's Fence Ltd. — founded 1948
Simpson's Fence Ltd. has installed and supplied fencing across Chatham-Kent since the same year.
Chatham Toyota — founded 1955
Chatham Toyota has operated as an authorized Toyota dealership in Chatham since 1955.
Syd Kemsley Florist Inc. — founded 1956
Syd Kemsley Florist has been a full-service Chatham florist since 1956.
Chatham Maroons — founded 1959
The Chatham Maroons junior "A" hockey club traces its roots to 1959, playing out of the historic Chatham Memorial Arena in the Greater Ontario Hockey League and winning Sutherland Cup championships in 1999 and 2025.
MC Business Solutions — founded 1960
MC Business Solutions has provided business technology and IT services in Chatham since 1960.
Brown's Auto Supply — founded 1965
Brown's Auto Supply, a family-run wholesale collision repair supply company, has served collision centres across southwestern Ontario from Chatham since 1965.
Want the full, current list? The Business Index tracks every confirmed founding year live, along with how many listings have a documented operating history of 50 years or more.
