| 1936 | Founded by Samuel G. Colt and appointed the district agency for Aetna Life Insurance Company. |
| 1939 | Samuel Adelson joined the Agency as vice-president. |
| 1952 | George R. Lagarce joined the Agency from Aetna Life. He became shareholder in 1956. |
| 1957 | Colt Agency purchased the Flournoy Agency of Pittsfield. The acquired agency was owned by Thomas Flournoy, MD a Pittsfield Physician. This acquisition brought with it the Pittsfield General Hospital Account. |
| 1958 | Colt Agency purchased the Sullivan and Farr Agency of Pittsfield. John A. Farr came with the acquisition and was appointed Treasurer of the Colt Agency. |
| 1959 | Mark L. Selkowitz joined the Colt Agency out of St. Lawrence University as a Sales Associate. His first purchase of Colt Agency stock was transacted in 1962. |
| 1961 | Colt Insurance Agency moved into its present location 101 South Street, Pittsfield. |
| 1962 | Colt Agency acquired the Robertson Agency of Pittsfield. |
| 1966 | Samuel Adelson retired as vice-president of the Colt Insurance Agency, Inc. |
| 1976 | Raymond P. Dotchin joined the Colt Agency from Crum & Forester Insurance Company where he was manager of their Springfield, MA regional office. |
| 1977 | Raymond P. Dotchin purchased shares of Colt Agency stock. Samuel G. Colt retired as President of the Colt Agency. |
| 1981 | W. Kelly Collins, Jr. joined the Agency from Aetna Casualty and Surety Company where he was a Commercial Lines underwriter in the Boston Office. |
| 1982 | W. Kelly Collins, Jr. purchased shares of the Colt Agency stock. |
| 1987 | George R. Lagarce retired as President of the Colt Agency. |
| 1997 | Mark Selkowtiz retired as President of the Colt Agency. |
| 1997 | Raymond P. Dotchin was elected President of the Colt Agency and W. Kelly Collins, Jr. elected Vice-President, Treaurer and Clerk of Corporation. Dotchin is responsible for Company/Industry Relations, Sales and Account handling. Collins is responsible for the Treasury, Personnel and Internal Operations, is Clerk of the Corporation and is also responsible for Sales and Account handling. |
| 1997 | Carolyn DiCarlo was promoted to Account Executive & Sales Associate. |
| 1998 | David M. Milligan joined the Colt Agency forming Colt Investment Services specializing in both Brokerage Services and Asset Management including Stocks, Bonds, Mutual Funds and Small Business Retirement Plans. |
| 1999 | Formed Main Street Insurance Agencies L.L.C. A marketing joint venture with Colt Agency, Wheeler & Taylor Agency and Blair Cutting & Smith Agency. |
| 2000 | Expanded Main Street Insurance Agencies with two additions to the venture. Herlihy Agency from Worcester, MA and Canary Blomstrom Agency from Feeding Hills, MA. |
| 2000 | John P. Quinto joined the Colt Agency as a Life Insurance and Financial Services Specialist. |
| 2001 | Formed a joint venture with Wheeler & Taylor and Legacy Banks to sell insurance products to Legacy employees and customers. |
| 2002 | Carla Prendergast appointed Sales Executive. |
| 2004 | Expanded the Colt Agency office to include 2500 square foot of 2nd floor office space. |
| 2005 | Raymond P. Dotchin passed away before he was to retire at year end 2005. |
| 2006 | W. Kelly Collins becomes President of Colt Insurance. |
2006
| Formed Main Street Program. A marketing joint venture with the Main Street Agencies. |
2007
2008
2010
2011
2012
2013
| Kim Knights promoted to Director of Operations and Account Executive.
Carolyn Dicarlo promoted to Director of Sales and Marketing.
Jenifer Powers promoted to Commercial Lines Manager. Heidi Gingras promoted to Personal Lines Manager.
Anderson, Bagley & May Insurance joined Main Street Insurance Agencies.
Audrey Hartley joined the agency as an Account Executive.
Main Street Insurance Agencies added six new partners from the former Alliance Berkshire, creating the new name Alliance Main Street.
Carolyn Dicarlo retires after 25 years of service.
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