Starting at Boston North Station, it ran to Fitchburg, MA, diverging from the Fitchburg Division in South Ashburnham, MA, and then through to Keene, NH, Bellows Falls, VT and White River Junction, VT.
[2] During the 1944-1945 season, buffet service allowed passengers to purchase light breakfast items such as eggs, cereal and toast from the Armstrong Company.
On August 28, 1945, the Flying Yankee was transferred to the Mountaineer but returned to the Cheshire Branch on October 15.
On February 1951, a Budd Rail Diesel Car, dubbed Highliners by the B&M, performed a week-long test on the line and replaced the Flying Yankee by 1952.
In December 1956, the Flying Yankee returned to the Cheshire route but retired on May 7, 1957 due to looming major maintenance needs[5] In October 1957, the Cheshire's route was curtailed to Bellows Falls and passengers bound for White River Junction had to transfer.