During the Fall and Winter of 2002, Bernard Forgea, Service Director for Cummington Ambulance, Francis Dresser, Service Director for Goshen Ambulance, and Douglas Mollison, Service Director for Ashfield Ambulance began meeting together to resolve an operational problem that was plaguing the 3 ambulance companies. All three ambulance services were staffed by volunteers and it was becoming more and more difficult to find volunteers who would serve during weekday business hours. They concluded that the only viable solution to this problem was to have full time paid staff during weekday business hours. Since none of the ambulance services had enough volume to afford to pay full-time staff, the three service directors resolved to join together as a new ambulance company.

Invitations were sent to the select boards of the towns of Ashfield, Goshen, Chesterfield, Cummington, Plainfield, and Williamsburg to send a representative to an informational meeting to discuss the issues. These representatives agreed that the proposed solution made sense and agreed to participate in the formation and operation of the new company. David Dann of Ashfield, Spencer Timm of Chesterfield, James Drawe of Cummington, John Monaghan of Goshen, Joe Sabourin of Plainfield, and Christopher Smith of Williamsburg along with the three service directors began meeting in the spring of 2003 to create the new ambulance company. From the Spring of 2003 through the Spring of 2004 they met weekly to develop the Articles of Organization, The Bylaws, the Personnel Policy, the pro forma budget, and all of the other necessities of an operating ambulance company. Highland Ambulance EMS, Inc. became an official corporation of the State of Massachusetts on September 17, 2003 and received 501(c)3 status from the IRS shortly thereafter.

After reviewing the run and billing histories of the three ambulance services and projecting expenses for fiscal 2005, the board determined that there would be a shortfall of $92,000. It was determined that the best way to make up this shortfall was to assess each of the member towns proportionately based on their annual town clerk census. This was done and all six towns voted unanimously to approve their assessment.

Highland Ambulance EMS, Inc. began operating on July 1, 2004. Michael Rock was hired as the Service Director on July 12, 2004.

Highland Ambulance operated in a management capacity for the three ambulance companies pending approval of Highland Ambulance's application for a state ambulance license. By late August, Michael had put together a consolidated run schedule for the three ambulance companies. Starting September 1, 2004 all personnel were scheduled through Highland and Cummington Ambulance ceased to operate as a Class I service. In March, 2005, Highland Ambulance EMS, Inc. received their license to operate as a Paramedic Level Class I Ambulance Service, leasing one of Goshen's ambulances. On July 1, 2005, Highland leased Ashfield's ambulance and the Ashfield Ambulance ceased to operate. Highland will continue to manage Goshen ambulance for billing purposes until Highland ambulance receives all of their insurance provider numbers. Highland will then lease Goshen's second ambulance and Goshen Ambulance will cease to operate as a Class I service.