Pretty much every "downtown" station on the New Haven main line in Fairfield County has at least one bar/restaurant in or adjacent to the station ("downtown" = more than a parking lot and a platform a la Green's Farms or Riverside). They range from the swanky (Tarantino Restaurant on Railroad Place in Westport) to the not-so-swanky (the pizza joint in the eastbound station at South Norwalk).
Away farther east, the deck of the Dog Watch Cafe in Stonington Borough https://goo.gl/maps/t1NobL5W39J2
has a Trains
-photo-issue worthy view of the Shore Line main crossing the Lambert's Cove causeway.
And up in Litchfield County, The Collins Diner in Canaan is actually in the forecourt of Canaan Union Station https://goo.gl/maps/LfACyRbvHLM2
, where once upon a time the Central New England crossed the Berkshire Line.
Somewhat related to this thread-- back in 2011 I mentioned the Berkshire Steel Rail Pale Ale at the Little Pub in Branchville (also still going strong, btw). I know nothing about this brewery other than they make good beer and are in Western Mass. However, in going to their website, it sure seems someone there knows his trains-- in addition to Steel Rail, their offerings include Gold Spike Kolsch and Hoosac Tunnel Amber Ale (with a locomotive emerging from the East Portal on the label.)