05/19/2026
From May 15 to May 21, 1938, the United States observed National Air Mail Week, marking two decades since the inception of the U.S. Air Mail. Berkshire County Postmasters, under the guidance of Pittsfield Postmaster Dennis P. Sweeney, organized a special celebration to honor this milestone, culminating in a historic event in Pittsfield on May 19, 1938. On the morning of May 19, special mail planes departed from Dalton, Great Barrington, Sheffield, and North Adams, each carrying mail with commemorative markings, or cachet. These planes arrived at Pittsfield Municipal Airport, near Barker Road, where their cargo was transferred at a temporary mail field station. The collected mail, weighing 300 pounds and representing a total of 25,000 letters, was carefully transferred to the cargo area of a Waco J5 aircraft. The manager of the Pittsfield Airport, H. Roscoe Brinton, who had recently taken an oath as an Official US Air Mail pilot, was selected to make the First Scheduled Air Mail Flight from Berkshire County. At 1:40 pm, Roscoe Brinton took off for Westfield, cheered on by an excited crowd that included Mayor Fallon and photographer Leo Lincoln, son of photographer Edwin Hale Lincoln. Lincoln, serving as Chairman of the Cachet Committee of the Berkshire Stamp Club, assured attendees that their letters, each bearing the special commemorative seal, would be delivered that very evening, May 19. It was a landmark day for Pittsfield and Berkshire County.
Images:
Preparing for the flight. Leo Lincoln, right, holds a bag of mail. Collection of the Berkshire County Historical Society.
“H. Roscoe Brinton signs receipt for Berkshire County mail at the request of Matthew D. Guiltinan, Pittsfield Postoffice foreman.” Berkshire Eagle, May 20, 1938
“Postal workers and others wave farewell to Brinton as he soars into the air with first air mail flow out of Pittsfield.” Berkshire Eagle, May 20, 1938
Berkshire County airmail cachet, featuring the Veterans War Memorial Tower on Mount Greylock, which had been dedicated five years earlier.