Though physically within the city, Chesterton retains a village high street, a good way to the east of the main town, though with New Chesterton running all along the north bank of the river from there to Castle Hill, the original village is physically joined to Cambridge itself.
A large council estate makes up part of the East Chesterton area. Milton Road (the A1309 and A1134) is the major arterial road through Chesterton, linking the centre of Cambridge to the southwest with the A14 road to the northeast.
The many pubs in Chesterton were a favourite refuelling place for the bargees when the river was the main local transport route.
It is believed that Grantaceaster to which Bede refers was Chesterton (not Grantchester, which took that name far more recently); Bede reports that Grantaceaster was the site of an old Roman town, to which monks rowed to salvage stone.