I've said for years, properly done (and right now I don't see HRCC doing it) weekend service to GCT (or even exchange at Danbury for now) is an option.
Leave Friday: 4:00 PM, arrive Canaan by 7:00 PM. You can turn on the wye, or continue to Great Barrington or even Pittsfield. Return Sunday.
If you really want, run a Saturday train down and back.
Yes, slower than driving, but no weekend traffic and most weekenders already have a car at their weekend place, or the rest of the family is there while they work in NYC so don't want a car in the city.
Yes, I know folks can drive over to NY and take the train from there, but that's still inconvenient.
You're not going to get enough traffic for daily service, but on the weekend, you just might get enough to cover operations.
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