The MTA experimented with such a bus, on weekends only, but there has been no bus service to Wassaic in recent years. A Great Barrington resident, Chip Elitzer, has been trying to see if we can get a bus service established that would meet all or most trains arriving/departing Wassaic, and make express stops along Rte. 7 in the Berkshires. He wrote about this in the Berkshire Edge (click to read the article) in 2017. Elitzer’s financial model, he said, demonstrated a possible break-even scenario that wouldn’t require a public subsidy, but to date there have been no further developments.
North of Danbury there is a 10 mph speed limit up to Brookfield depot and then 25 mph. in the last 20 years, Mr. Hanlon has done the absolute minimum maintenance on the line. It is very hard to run passenger trains on this. CT is interested in Shore Line revamping and speed increases. NARA is the best bet for Housey passenger rail, possibly HSR from Pittsfield to Montreal
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I would be optimistic about the prospects for the Flyer if Connecticut would join the effort. CT wants MA to subsidize the construction costs in CT, something that MA seems unwilling to do. CT would benefit from the Flyer. Even if their benefits were less than MA’s, I think it would be enough to justify their participation without a subsidy. Besides the conventional economic benefits, CT would see fewer cars using their roads as a throughway between NY and MA.
Peter Pan ran a bus service between NYC and the Berkshires. They have stopped it, and it is not clear if they will resume service. The fact that they still run other service, but not NYC–Berkshires, makes me doubtful. A bus service between the Berkshires and the Wassaic train station could be a good alternative. But passengers need to be confident that delays on a travel leg would not cause them to miss the connection and strand them.
On a longer term basis, train service between NYC and the Berkshires would be great. The construction and operating costs would be a small fraction of the East–West proposals that have attracted much attention in recent years. But NYC– Berkshires has been talked about on-and-off since the early 1970’s. Even if the various authorities approved it, it would take time to upgrade freight-only tracks and other facilities. I am not holding my breath for it.
Your information is generally correct but out of date. You should consider reading about what has already been done, and the contract related to restoring passenger rail signed by the MassDOT in 2014. The track in MA is being upgraded now at a cost of some $30 million.