U.S. Route 44 is an east–west United States highway that runs for 237 miles (381 km) through four states in the Northeastern region of the United States. The western terminus is at U.S. Route 209 and New York State Route 55 in Kerhonkson, a hamlet in the Hudson Valley region of New York. The eastern terminus is at Massachusetts Route 3A in Plymouth, Massachusetts.
US 44 begins at US 209/NY 55 in the hamlet of Kerhonkson in Ulster County. Route 44 is about 66 miles (106 km) long in the state, progressing through Ulster and Dutchess Counties. The route crosses into Connecticut after intersecting with New York State Route 22 in Millerton.
From the New York state line at Salisbury to the Rhode Island state line at Putnam, US 44 runs for a total of 106.03 miles (170.64 km) in Connecticut. Most of US 44 is known in the state as the Jonathan Trumbull Highway. It begins as rural arterial road in Litchfield county, going through the towns of North Canaan, Norfolk, Colebrook, Winchester, Barkhamsted, and New Hartford. It is a 2-lane road with 4-lane sections in Winchester.
In Canton, US 44 is joined by US 202 and becomes a mostly 4-lane principal arterial road serving the Hartford metro area. US 44 continues through Simsbury, Avon, and West Hartford. US 202 splits from US 44 in Avon following the route of Route 10 after overlapping for 5.3 miles (8.5 km). US 44 then enters the city of Hartford along Albany Avenue, then goes up onto I-84/US 6 to cross the Connecticut River on the Bulkeley Bridge. In East Hartford, US 44 then returns to surface roads right after crossing the river. It becomes a 2-lane minor arterial road through Manchester, Bolton, Coventry, and Mansfield, then becomes a rural road through Willington, Ashford, Eastford, Pomfret, and Putnam. In Manchester, US 44 overlaps with US 6 for 6.9 miles (11.1 km) up to Bolton until just after the eastern terminus of I-384. This segment of US 44 up to Willington is known as the Boston Turnpike while the segment approaching Rhode Island is called Providence Pike.
US 44 runs 26.2 miles (42.2 km) in Rhode Island. During this part of the road, Route 44 is often referred to locally as "Putnam Pike" as the road runs through Rhode Island and into Putnam, Connecticut. US 44 enters the state at Glocester, traveling through Chepachet and Harmony, villages of Glocester, as it heads towards the village of Greenville in the town of Smithfield. US 44 has a junction with I-295 in Smithfield at a cloverleaf interchange. Soon after the I-295 junction, US 44 enters the town of North Providence along Smith Street, then enters the city proper of Providence after another 1.7 miles (2.7 km). In downtown Providence, US 44 separates into one-way pairs. Eastbound US 44 runs along Canal Street and South Water Street (via a section of Memorial Boulevard). Westbound US 44 runs along South Main Street and North Main Street. US 44 joins I-195/US 6 at Exit 1E as they cross the Seekonk River into East Providence. US 44 leaves I-195/US 6 at Exit 1G just after crossing the river and continues east towards the Massachusetts state line along Taunton Avenue.