A 2-year pilot program begins in July that provides rail service from New York City to the Berkshires. The Berkshire Flyer service will run on weekends leaving from Penn Station in New York Friday afternoons arriving in Pittsfield Friday night. The return Flyer will depart from Pittsfield on Sunday afternoon returning to NYC according to WWLP.

The service has had its skeptics. They claim that one train in and one train out two days later is not at all convenient if the goal is to enhance tourism traffic to the Berkshires. Also, the route has come under fire with additional stops in Albany and other NY locations. The return route heads north to Albany before heading south toward NYC.

Massachusetts Governor Charlie Baker sees the rail service as a positive for bringing tourists to the Berkshires. WWLP posted a statement by Baker… “Western Massachusetts and the Berkshire region offer a whole host of cultural and recreational opportunities during the summer and we hope this pilot service will encourage even more visitors to this part of our state.”

An evaluation following the 2-year test will determine whether it is feasible to continue the program after the two-summer test according to WWLP. In addition to Amtrak, the Massachusetts and New York Departments of Transportation collaborated on the service. The first Berkshire Flyer is scheduled to leave Penn Station on July 8th.

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Stacker compiled a list of 50 attractions--state by state--to see along the drive, drawing on information from historic sites, news stories, Roadside America, and the National Park Service. Keep reading to discover where travelers can get their kicks on Route 66.

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