[1] The A249 begins close to Maidstone town centre, heading eastwards from the southbound A229 Lower Stone Street along first Mote Road and then along Wat Tyler Way.

At the top of Wat Tyler Way, where that road meets King Street, the A249 occupies a small gyratory system that joins the A20 (heading east to Ashford).

After passing Vinters Park, it reaches the north end of the town at the Chiltern Hundreds roundabout (named after the adjacent pub).

This break occurred during the 1990s, as the result of works to widen and upgrade the former A20(M) Maidstone Bypass section of the M20 to remove a bottleneck on the newly completed motorway.

Further on, the road passes a large lay-by on the northbound carriageway, which was closed in 2005 after local residents complained that it was a haunt of doggers.

In 2020, Kent County Council installed mobile CCTV cameras along the A249 in anticipation of HGV backlogs due to Brexit.

[5] From September 2021, National Highways are carrying out improvements to J5 of the M2 at Stockbury, which will involve the construction of a new flyover of the roundabout for A249 traffic heading through the junction, and new slip-road connections between the M2 and the A249.