The A523 enters Cheshire from Staffordshire near Rushton Spencer, and shortly afterwards meets the A54 at the Bosley Crossroads. For the next few miles north, the road parallels the Macclesfield Canal until the town of Macclesfield itself is reached. Moss Rose, Macclesfield Town Football Club's ground, is adjacent to the A523 in the south of the town. Most of the town centre is bypassed by The Silk Road, a 1990s relief road, partially built on the former Macclesfield to Marple railway line. After meeting the A536 and A537, a dual carriageway is reached for a few miles. North of Macclesfield, the road heads along a single carriageway towards the small town of Poynton. The centre junction in Poynton with the A5149 was recently remodelled as a "shared space" junction with equal priority for pedestrians and motor vehicles. A full bypass of Poynton is planned, to meet up with the A555 SEMMMS Relief Road, which is progressing towards construction in the next few years.
Beyond Poynton, the A523 enters Greater Manchester for its last 3/4 mile.