This line was built in 1880 as part of the New York City and Northern Railroad between New York City and Brewster. The original route included a wooden trestle over recently created Tarrytown Reservior. The 80-foot trestle proved troublesome for a number of reasons, so a longer route was laid around the western end of the reservoir the next year. (The route over the reservoir was abandoned in 1882, with the trestle coming down the year after.)
Coincidentally, the route cut through the property of one John D. Rockefeller at Pocantico Hills. Disturbed by the frequent passings of both passenger and freight trains across his otherwise serene bit of land, he eventually worked a deal with then owner New York Central to reroute the entire line to the east side of the hills along the Saw Mill river (a shorter route, which also moved the line out of sight of Rockefeller's lavish home) for the grand sum of $200,000. Thus, in 1929, the NYC abandoned the line between Eastview (which Rockefeller also razed after paying its residents to move away) and Briarcliff Manor in favor of the newly-laid line between those same points.