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...although at the terminus one is actually heading pretty much east.  At the time of this photo, the endpoint was at the junction with US 17...

​...but in 2006 mainline US 17 traffic was rerouted onto a bypass.  US 258 still ends at the same intersection...

​...but that road is now designated Business 17, as the signage ahead indicates:

This next image shows the view from northbound Business 17:

The south beginning of US 258 is to the left, as indicated by this assembly posted in the gore ahead:

...and then the assembly shown here is posted on the gore:

Drivers who turn that direction are soon greeted with a "Begin" confirming assembly:

This photo was looking east on what is now Business US 158.  But originally, US 158 came in from the left (with the "Do Not Enter" sign) and continued straight ahead, so this is where US 258 ended:

This shot was taken from the opposite direction,looking west on Business 158.  But it was originally mainline 158, and it continued to the right, so straight ahead was the north beginning of US 258:

That is a dead-end road now; the signal visible straight ahead (at the west end of Business 158) is the modern functional equivalent of that historic junction:

I am unaware of any evidence that the route has ever been cut back from Old Point Comfort, but at times thede facto endpoint of US 258 has been at its junction with VA hwy. 143, because beyond there was a gate to the military base, and it has not always been open to civilians.  This photo was looking south on Mercury Boulevard, and the light ahead is VA 143:

Just beyond the light, the gatehouse at the entrance to Ft. Monroe is visible.  That became an inactive base in 2011, so now one can freely continue to the official end of US 258, which is where Ingalls Road ends at Old Point Comfort:

According to VA DoT records, that is still the official endpoint of US 258.  

​Heading the opposite direction, the sign shown in this photo was formerly posted at the junction with VA 143:

The faded directionals in that photo read "West 143" and "South 258".  Astute observers might well wonder: if west was to the left, then how could south be to the right?  The answer is that this is one of those examples where a US highway whichultimately tends in a particular direction (south) cantemporarily head in another (north).  In this case, US 258 ultimately goes south from the Hampton Roads area and ends in North Carolina.  But from its "north" terminus, it actually heads further northward into Hampton, before turning to the west to serve Newport News, and then to the southwest to cross the James River.  For this reason, the "northernmost" segment of US 258 may have been signed east-west at one time. 

Anyway, those 143 and 258 signs were removed years ago.  Now, if drivers stay to the right and continue up Mercury, they must go another mile or so before encountering the first indication that they are on US 258.  This photo shows the reassurance sign posted after the junction with VA 169:

​That perspective is actually looking northwest, and ahead the road bends even more towards the north for a couple miles, before curving more towards something resembling a southbound direction of travel.