When the NY 29 designation was created in the 1920s, the route extended from Barneveld in the west to Salem in the east.

Since that time, the route has remained virtually unchanged, excluding minor realignments in Fulton County.

NY 29, however, curves south, paralleling Spruce Creek to the village of Dolgeville, located on the Herkimer-Fulton County line.

After crossing downtown, the concurrency ends with NY 67 following East State Street toward Amsterdam.

NY 29 then reaches Comrie Avenue, turning left to join with NY 30A briefly to an intersection with Briggs Street, a westward extension of the major business section of that stretch of Comrie Avenue.

Past Mayfield, NY 29 passes through both the village and town of Broadalbin before crossing into Saratoga County.

Upon crossing into Milton, the route initially curves south to serve the hamlet of Rock City Falls before resuming an easterly track south of the Milton-Greenfield town line into the Saratoga Springs city limits.

At first, the land surrounding NY 29 is largely undeveloped; however, the amount of open space rapidly declines as the route continues toward the city center.

NY 29 then follows Ferry Street out of the village and across the Hudson River on the Schuylerville Bridge into Washington County.

Route 37, meanwhile, was altered twice by 1912 to begin in Dolgeville and follow modern NY 29 east to Johnstown.

East of Johnstown, it was tentatively routed on Fulton County's CR 107 and current NY 30 to Broadalbin, where Route 37 rejoined the path of modern NY 29 and followed it east to Saratoga Springs.

The segment of current NY 29 between Saratoga Springs and Grange Hall Road west of Schuylerville became part of Route 25 by 1920.

The route also extended farther out in both directions as it initially began in Barneveld and ended south of Salem.