US 44 is an east/west route from Kerhonkson, NY, to Plymouth, MA. It begins at US 209 and runs east. It is multiplexed with NY 55 for about half of its length in New York. At Mohonk Preserve, there is a switchback, and US 44 turns to the south for about a mile before curving to the east again. It passes under the New York Thruway (I-87), but there is no interchange. US 44 reaches US 9W in Highland. The two routes are multiplexed for about half a mile, and then US 44 splits off and runs east again to the Mid-Hudson Bridge, a suspension bridge across the Hudson River to Poughkeepsie. On the other side of the bridge, US 44 is routed along parallel sets of one-way streets. Eastbound traffic follows Church Street, Baker Street, and West Haight Avenue. Westbound traffic follows Maple Street, Mill Street, and Columbus Drive. After about two miles, the eastbound and westbound lanes come together. US 44 and NY 55 split at this point. US 44 is called Dutchess Turnpike east of the split. It is a four-lane divided highway for a short distance, after which the divider ends and US 44 narrows down to two lanes. It runs northeast, to Amenia, where it joins NY 22. The two routes are multiplexed for a few miles to Millerton, where they split. US 44 runs east as Main Street for about a mile to the Connecticut border. It continues into Connecticut as Millerton Road.
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