North of Middleport, NY 271 traverses an area of the county dominated by farmland.

The routes head north on Main Street, passing two large residential blocks and the Middleport post office before entering the village's central business district.

[4] As the route leaves Middleport for the town of Hartland, the homes become more spread out as the residential areas give way to open farmland.

The route joined NY 3 here, following it northeast through the village on Telegraph Road and Main Street.

[2] NY 271 was truncated on its southern end to Telegraph Road in Middleport in the early 1940s.