Who's supposed to install the rail? And pay for such installation? That could be your problem right there.
Here's the link to the piece: http://railfan.com/housatonic-today/
There's also a pretty good Facebook page, of which Mr. Jacobs I think is the admin: https://www.facebook.com/groups/fansofthehrrc/
Brief, fair-use quote per forum policy:
Nestled in the Berkshire Hills of western Massachusetts and Connecticut is a hidden gem of railroading. Housatonic Railroad is a 120-mile short line, headquartered in Canaan, Conn., a small town 47 rail miles north of Danbury, Conn., and 37 rail miles south of Pittsfield, Mass. Canaan is the base of operations, home to the locomotive shops, dispatcher, clerk, main office, and maintainers, and is where most of the train crews report for duty.
The “new” Housatonic Railroad Company (HRRC) was chartered in July 1984 by entrepreneur John Hanlon, who began running passenger excursions from Canaan to Cornwall Bridge, Conn., a distance of approximately 15 miles. Enjoying modest success, the remainder of the line was reopened in 1989 all the way to New Milford, where HRRC could interchange with Conrail. It was then Housatonic began servicing its first freight customers in Canaan.
By the time Housatonic took over in 1993, the only remaining freight customers on the upper Harlem Line were King Lumber in Golden’s Bridge and a Grand Union warehouse in Mount Kisco. The warehouse was closed by 1995 when the supermarket chain went bankrupt, and King Lumber switched to truck delivery soon after HRRC began regular operations. Despite a lack of customers, freight rights remain active…
I thought MNRR terminated the freight rights, and MNRR now owns the portion west of the state line. AFAIK, the last train HRRC operated over the Beacon west of Danbury would have been Strates.
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I know there's a fair amount of derision on here for the HRRC; certainly, some of it is justified. But without them, this route through the Berkshires would be a rail trail. Keep that in mind. I drove it a couple weeks ago as far as Canaan from Danbury. Stopped at a few old station, got some nice shots. I'll say this much: there's a WHOLE LOT OF NOTHING along the Housatonic River Valley! Very scenic though. Route 7 is in pretty bad shape.
At most, regular passenger service should be extended to New Milford, but I'd add that a weekend excursion train during spring/summer/fall up to Kent and back would be nice; very touristy type towns.