US 250 all over the place 1936 Augusta County

US 250 rebuilt 1958 Augusta County

In May 1939 (CTB), The Route 250 Association requested that US 250 be extended along US 60 east to Old Point Comfort. There was no decision given on that in the CTB but this did not ever happen.
US 250 had a gap in it at Shadwell. To connect, one had to use VA 22 to SR 729 (no longer connects to VA 22) south to SR 731 east to US 250. The gap was closed about 1939 with US 250's current bridge over the railroad at Shadwell.

US 250 gap at Shadwell 1936 Albemarle County

US 250 continuous 1958 Albemarle County

Sometime in the late 30s, US 250 was given its current routing just west of US 29, leaving behind SR 601/754.
In Jan 1941 (CTB), US 250 was given its current routing bypassing the village of Afton, leaving behind SR 750 and a bit of VA 151 (now VA 6).
In Nov 1942 (CTB), US 250 was removed from Crozet and placed on its current bypass there. This was a replacement of VA 240. The E-W part of the old route became VA 240 and the N-S piece became VA 230 (now also VA 240).

US 250 through Crozet 1936 Official

US 250 bypasses Crozet 1944 Official

In Sept 1945 (CTB), US 250 was removed from SR 796 in western Albemarle County. Also, US 250 bypassed Yancey Mills, leaving behind SR 797.
In Nov 1948 (CTB), US 250 was rerouted within Charlottesville. In this change, WB now used High/Preston/Grady/Rugby/Main (this is still WB US 250 Business' route). EB now used Main/Water/7th/High.
The Nov 1953 (CTB) reroute of US 60 WB in Richmond to leave Broad at 11th may have extended US 250 along Broad to 11th. Almost certainly US 60 WB traffic would've seen a US 250 shield there, though this 1960 picture (Adolphus Rice) showed a TO US 250 shield.
Between 1955-58, US 250 was moved to its bypass of central Waynesboro, replacing US 250-A. The old route on Main St remained US 340.
In March 1962 (CTB), US 60 WB left Broad at 9th instead of 11th, so US 250 was likely truncated back to 9th. Unfortunately, county maps of the 1950s and early 60s do not show detailed routings in downtown Richmond.
In Oct 1968 (AASHO), US 250 was placed on its current Charlottesville Bypass replacing US 250-A. US 250 through Charlottesville became US 250 Business (EB has been rerouted since).

US 250 initial C'ville route (shown as then-VA 5) 1933 Official

US 250 loops up on Locust east of Downtown 1945 Albemarle County

US 250 wide splits in C'ville 1958 Albemarle County

US 250 bypasses C'ville 1970 Official

US 250 shown explicitly ending at I-95
AASHO Route Log late 1960s

US 250 overlay shown to end at 9th 1969 Henrico County

US 250 extended east. 1975 Henrico County

Improvements: Upon designation, US 250 was paved everywhere except WV Line to Monterey.
US 250 was paved west of Monterey in 1939.
The first multilaning of US 250 occurred by 1954, on Broad St out to Staples Mill Rd
In 1958, 4-laning was extended west to Dickens Rd
In 1969, US 250 was 4-laned from US 29 east to just short of US 250 bus/VA 20 when it was placed on the Charlottesville Bypass.
In 1970, US 250 was widened from SR 654 Barracks Rd to US 29; Broad St was 4-laned out to Glenside Dr.
In 1972, US 250 was 4-laned from US 250 Bus west of Charlottesville halfway to SR 654 Barracks Rd
In 1975, US 250 was multilaned the rest of the way between US 250 bus and SR 654.
In 1978, US 250 was multilaned around the I-64 Short Pump area
In 1979, US 250 Broad St was 4-laned from Glenside Dr to Parham Rd.
In 1983 or 1984, US 250 Broad St was 4-laned from Parham Rd to VA 157.
In 1988, US 250 was widened from Staunton to Waynesboro
In 1992, US 250 was 4-laned from VA 157 west to I-64 Short Pump
In 1993, US 250 was 4-laned from I-64 Shadwell west to Locust Ave (Charlottesville Bypass now all 4-laned, even though officials all through the 1970s showed this erroneously).
In 1997 or 1998, US 250 was widened from I-64 Short Pump west to the Goochland Line.
In 2003, US 250 was multilaned from the Henrico-Goochland Line west to SR 623
US 250 has substantial sections of 6 or more lanes: VA 288 east to downtown Richmond
Posted:  Fully posted; Staunton cutouts replaced about 2013; Highland County still had a couple sets into 2013 (status unknown); Richmond cutouts went away in mid-2000s.
In the late 1990s there was an error VA 250 shield WB leaving VA 157.
US 250 is poorly posted east of US 1-301 and back to at least 1981 is not posted east of I-95.
Multiplexes:  VA 42 (0.47 mi)
US 11 Bus (0.76 mi)
US 11 (0.07 mi)
US 340 (0.19 mi)
US 29 (2.21 mi)
VA 20 (0.26 mi)
US 33 (3.06 mi)
Legislative names: The Jefferson Hwy, from Staunton to Shadwell except not Charlottesville Bypass (3/9/22 designation predates US 250); The Woodrow Wilson Pkwy, from ECL Staunton to the Blue Ridge Pkwy (since 2/28/66);
Other names:  Highland Tpk (Highland Co); Hankey Mtn Hwy (Highland Line to Churchville); Churchville Ave (Churchville to Staunton); Augusta St/Johnson St/Greenville Ave/Richmond Rd (Staunton); Main St/Broad St (Waynesboro); Rockfish Gap Tpk (Blue Ridge Pkwy to Mechum River); Ivy Rd (VA 240 to US 29); Monacan Trail Rd (US 29 duplex); Long St (Charlottesville); Richmond Rd (Albemarle Co east of Charlottesville, Fluvanna Co); Three Notch Rd (w Louisa Co segment); Broad Street Rd (Goochland Co, E Louisa Co segment); Broad St (Henrico Co, Richmond)
Scenic Byway:  Blue Ridge Pkwy to US 29/250 Bus (12/17/83)
Truck Route: A posted truck route for Staunton appeared about 1999. Runs from US 250 along VA 261 to US 11 north to VA 262 west back around to US 250 west of Staunton. It is very well posted.
Comment: US 250 is kind of a forgotten highway in most parts of Virginia. It is closely paralleled by I-64 from Staunton to Richmond and west of Staunton runs through pretty unpopulated territory.
US 250 is however a wonderful, peaceful drive when not in the cities. West of Staunton it is quite scenic, especially in Highland County.
US 250 has several mountain range crossings west of Staunton. The worst is at the Augusta-Highland Line but the others are not all that bad. The crossing at Afton Mtn can actually be driven at 55 mph.
VDOT Traffic logs back to at least 2001 say that US 250 is on split streets in downtown Staunton, with WB using New St. However, US 250 is not posted this way in the field.
US 250 is misidentified as VA 5 in both the Staunton and Charlottesville insets of the 1936 Official.