After entering the state from the town of North East, New York just east of the village of Millerton, US 44 is a rural arterial road. It is briefly duplexed with Route 41 for 1.67 miles through the center of Salisbury. After crossing into North Canaan, it is duplexed with US 7 for 0.33 miles through the village of Cannan. After leaving the village, it enters Norfolk, where it has a brief (0.34 mile) duplex with Route 272 in the center of town. After passing through the western part of Colebrook it enters the town of Winchester. As US 44 enters the village of Winsted, it begins a 2.14 mile concurrency with Route 183, 0.33 miles of which is joined by Route 8 in a triplex. At the east end of the village, Route 8 leaves to the south on an expressway, while Route 183 leaves to the south about 100 yards later. US 44 continues southeast through the towns of Barkhamsted, and New Hartford before entering Canton. In Canton, US 44 becomes a 4 lane primary suburban arterial road as it is joined by US 202 for a 4.3 mile concurrency to the center of Avon. As US 202 leaves to the north, US 44 is joined for the next 0.74 miles by Route 10. After climbing Avon Mountain, it enters West Hartford, passing along the northern part of the town and becoming an urban street as it entes the northern part of Hartford. After passing along Albany Avenue, and Main Street, US 44 turns east onto a pair of one-way streets (Morgan Street North and Morgan Street South) that straddle I-84 and US 6 and cross under I-91 with the only direct access being from Morgan Street South to I-91 South. US 44 then joins I-84 and US 6 for about 0.25 miles to cross the Connecticut River on the Bulkeley Bridge into East Hartford before exiting almost immediately onto Connecticut Boulevard. It briefly duplexes with US 5 on Main Street in East Harford center before turning east onto Burnside Avenue. After entering Manchester, it meets I-84 once again at exit 60, and is joined in a concurrency for the next 7 miles by US 6, which leaves its I-84 concurrency at this point. The road then enters Bolton, where it meets the east end of I-384 at Bolton Notch. US 44 and US 6 briefly join the stub end of the expressway before US 6 splits off to the southeast.