|Length:||8.1 miles (13 km)|
|Meets:||A355, B4441, A4154, B485, B4505, A41, A4251|
|Old route now:||A404|
|Route outline (key)|
We start on the A355 on the edge of Old Amersham, outside Amersham's large TESCO superstore, and travel up Station Road to Amersham on-the-Hill. After passing under the railway (the London Underground roundel on the bridge reminding us that this part of Buckinghamshire is served by the Metropolitan Line), we skirt the edge of Amersham's main shopping area, turning right at Dr Challoner's Grammar School and veering left at the double mini-roundabout with the B4441 at Oakfield Corner. We meet the A4154 from the A404 towards Little Chalfont outside the Boot and Slipper pub and enter Chesham Bois.
The A416 in Chesham Bois avoids much of the village - going through the woods on the west side of the village, with houses on side roads (and the few on the A416) set back a long way from the road. However, there is some development close to the road near the north of the village. We continue north, and head down the hill into Chesham.
At the bottom of the hill, we hit a roundabout next to the Football club and the A416 becomes built up again. We cross the river Chess and then go alongside it until a right turn with the former B485 for Waterside and Chesham Moor. We avoid the pedestrianised High Street on a purpose built relief road. After a roundabout (which gives access to the B485 from the north, via a U-turn, as well as to a car park), the road is briefly D2 with very narrow lanes, until the B485 junction, which only allows access to the northbound carriageway. We head alongside the Chess, which has joined us again, and Chesham Park as an S4, still with very narrow lanes, and have a big roundabout for Chesham Town Centre and the road to Chartridge. We rejoin the original route at a roundabout, where turning up White Hill cuts a corner en-route to Hemel Hempstead.
Heading through a densely built-up part of Chesham, the A416 feels hemmed in, with houses close to the road and slightly narrow lanes. After the B4505 leaves for Bovingdon and Hemel Hempstead to the right, the right hand-side opens up a little bit. At a mini roundabout, the A416 turns right while the road up the valley to Cholesbury continues straight on. The road ceases to be built up, but still has narrower lanes than to the south of Chesham. The road reenters open country and passes through the village of Ashley Green.
We cross the county boundary into Hertfordshire and almost immediately come to a roundabout with the westbound slips to the A41. We cross the A41 on what seems like a long and bent dumbbell to a second roundabout with the eastbound slips. Ashlyns School lays straight ahead and we take a sharp left than right and enter Berkhamstead. we start a gradual descent surrounded by large houses and large gardens, this must be the posh end of Berkhamstead. We pass Berkhamstead Collegiate School on the right with its playing fields below us in the bottom of a dip.
We at last come into Berkhamstead town centre and terminate at a staggered cross roads traffic light junction with the A4251 in Berkhamstead High Street which seems remarkably busy despite its traffic calming and bypass.
From 1922 to 1935, the A416 was twice as long as now, going from the A4 to the west of Maidenhead to the A41 (now A4251) at Berkhamstead. However, in 1935, it was decided that the Amersham-High Wycombe-A4 road would be better numbered as an extension of the A404. The A404 between High Wycombe and the A4 has been massively upgraded over the years, and little runs on the A416's original route (which went through Marlow and Bisham, for instance, before ending on the A4 at Littlewick Green).
In Chesham, St Mary's Way was built and a one-way system created in the early 1970s. Then the High Street was downgraded and St Mary's Way made two-way.