[1][2] Eight round trips per day would have followed the Housatonic Railroad from Pittsfield through Connecticut to Southeast, New York, where they would have taken the Harlem Line to Grand Central Terminal.

[5] The commuter rail project failed to progress due to lack of interest from the administration of Connecticut Governor Dannel Malloy.

[6] In 2017, the Massachusetts legislature began new efforts toward a summer tourist train, not commuter rail, between New York City and the Berkshires.

Eddie Sporn, a Berkshire-based consultant, was researching the topic of restoring passenger rail service and sent an outline of plans to State Senator Adam Hinds.

[9][10][11] The service pilot was originally scheduled to begin in June 2020, but was delayed due to the COVID-19 pandemic and questions around the program's legal sponsorship.

[18] The 2022 season saw nine total Berkshire Flyer round trips, carrying 401 passengers northbound to Pittsfield and 418 riders southbound.

This required a new agreement with track-owner CSX, who desired the construction of a passing siding at Joseph Scelsi Intermodal Transportation Center.

[23] Connecting bus service (possibly Amtrak Thruway) between Albany–Rensselaer and Pittsfield may be added after the Berkshire Flyer season ends.