The B744 is a secondary road in Ayrshire. The road was originally unclassified but gained its number in 1935.
The road starts on the A70 at Belston, a couple of miles east of Ayr, and heads northeastwards. It's not long before the River Ayr is crossed via a narrow bridge, after which the road continues on to Annbank, where it runs along the main street to a T-junction on the B742. The road turns right for the first - and shortest - multiplex along its route: little more than a bridge over a railway line.
After regaining its number at a triangular junction the B744 continues its northeasterly course across undulating terrain, although the road is now narrower than before. After another railway bridge we reach another T-junction and there's another multiplex east, this time along the B743 for a short distance uphill. Another mile or so across the open fields (now S2 once more) takes us to Tarbolton. We reach the B730 on the southern edge of the village and multiplex with it through town along Montgomerie Street. As the B730 bears left to pass the church the B744 turns right to regain its number. It heads north along Burns Street to a T-junction on Garden Street. A spur of the B744 heads left to rejoin the B730 whilst the mainline TOTSOs right and zigzags back into open country.
After crossing the Water of Fail the road climbs onto a ridge and shortly TOTSOs left; the unclassified road ahead continues to Mauchline. We descend to cross a railway line and then meet the A76, which is crossed at a slightly offset crossroads. After crossing the Cessnock Water the road turns more northerly and continues across the fields. There's a detour to the east for no apparent reason, after which the road descends steeply into Galston. The road ends at a T-junction on the A719 on the western edge of town.