[4] The Boston section of Amtrak's Lake Shore Limited serves Pittsfield with one train in each direction daily.

[1] Peter Pan Bus Lines serves Pittsfield with two daily round trips on its Albany-Springfield-Providence route.

Peter Pan's Bonanza Bus division serves Pittsfield with two daily round trips on its New York-Danbury-Williamstown route.

[9][10] An 1876 history of the city reported that:[9] The flames presented a beautiful spectacle, as they swept through its large, hollow, wooden columns, and no regret for the loss of the building checked the enjoyment of the scene.

[9] On April 7, 1866, the Massachusetts General Court passed a law authorizing the construction of a union station at West Street facing Park Square.

Berkshire County was authorized to build a bypass of West Street under the tracks to eliminate the level crossing and provide room for the depot.

[13] Four decades after its construction, Union Station was proving too small for its role as the principal railroad hub of Berkshire County.

In 1908 local residents began agitating for a larger station, and William H. MacInnis made it a platform of his mayoral candidacy.

[1][12] Constructed in the Beaux Arts style of red brick with white terra cotta trim, the station was more than twice its predecessor's size at 17,953 square feet (1,667.9 m2).

[1][12] Modern conveniences included all-electric chandeliers, thermostat-controlled heat, an intercom for announcing trains, and a restaurant inside the station building.

[8][17] Around 1913 the New Haven planned to use the Housatonic as part of a New York-Montreal through route to compete with the NYC, but this never materialized and service levels were never high.

[21] Berkshire Division service began to decline before World War II, when increased automobile availability reduced the appeal of travel by train.

In March 1964, the Interstate Commerce Commission authorized the NYNH&H to cut all Berkshire Division services except the weekend trips.

[18] B&A service was also cut due to financial problems in the late 1930s and again after World War II; by 1950, Pittsfield was served by eight Boston-Albany round trips per day.

[17] The two daily trips to North Adams (which ran as shuttles from the Harlem Line at Chatham or the Water Level Route at Albany in their final years) ended in 1953.

In January 1960 the NYC received permission to discontinue all B&A service that April, but public outcry prevented full cancellation.

[17] Still facing losses, the B&A was finally fully absorbed into the NYC in 1961, effectively subsidized by its popular New York commuter service.

[1] Although preservation attempts were made in 1966, the Union Station building was too deteriorated to save, and it was demolished for urban renewal efforts in 1968.

[25][26] An Amshack (a small aluminum and Plexiglas bus shelter) with a bare asphalt platform was built in downtown Pittsfield near the former Union Station.

[25] In the late 1980s, local officials began to consider constructing a new station to serve both Amtrak trains and the Berkshire Regional Transit Authority, which had taken over private bus services in the area in 1974.

Groundbreaking was held in August 2002; completion was originally scheduled within a year but delayed due to an unusually cold winter and the primary steel supplier going bankrupt.

[30] In May 2018, the Massachusetts Senate approved funds for a pilot of the Berkshire Flyer, a seasonal extension of one weekend Amtrak Empire Service round trip to Pittsfield.