Southport to Fayetteville:
NC 87 was born in late 1937 as a replacement for the second NC 28. It initially ran from Fayetteville southeast through Elizabethtown and ended at US 74-76 near Acme.

NC 28 #2

NC 87 replaces NC 28

In 1952, NC 87 was extended east along US 74-76, then southeast as new primary routing to US 17 Winnabow, then southeast replacing NC 303 to end at NC 130 (now NC 211) in central Southport. NC 87 duplexed with NC 130 to this location.

NC 303 #2

NC 87 replaces NC 303

In 1969, NC 87 was routed around Acme, leaving behind "Old NC 87"
In 1980, NC 87 was placed on new limited access routing in the I-95 area, leaving behind Wilmington Hwy.
Sometime after 1968, NC 87 was removed from its NC 211 duplex into Southport's downtown. A good guess would be when NC 211 was extended out to the ferry between 1988-90.
Between 1969-82, NC 87 was rebuilt northwest of Duart to the sweeping arc it uses to reach Cumberland County. Most of the old road which passes near the Huske Lock and Dam is not public road today.
In 1997, NC 87 was added to more limited access routing from the I-95 area to US 301, leaving behind more Wilmington Hwy.
Also in 1997, NC 87 was placed on a new bypass south of Elizabethtown, leaving behind NC 87 Business.

NC 87 through Elizabethtown

NC 87 bypasses Elizabethtown

Fayetteville:
From 1937-40, NC 87 north ended at the US 15A-301 jct (Gillespie at Person). In 1940, NC 87 was extended through the city, replacing NC 24. NC 87 headed west on Person St, Hay St and Fort Bragg Rd out of town.
Between 1945-49, NC 87 was rerouted by switching with NC 87-A. Now NC 87 left Hay St at Robeson St then curled northwest on what is now Bragg Blvd.
In 1958, NC 87 was rerouted from the south. NC 87 now followed the new (current) US 301 alignment north to Grove St, then went west until the road (now Rowan St) ran into Bragg Blvd. The old alignment became all secondary except Gillespie St was still part of US 301-A.
In 1970, NC 87 was removed from Bragg Blvd and instead left Rowan St with NC 210 Murchison Rd. Bragg Blvd remained part of NC 24.
In 1997, NC 87 was placed on new freeway which connected to US 401 Bus. NC 87 then was placed back on NC 24 Bragg Blvd. The old route remained US 301 and NC 210.
In 2015, NC 24-87 was removed from Bragg Blvd from Spring Lake south to the 295 freeway. Instead it was placed onto 295 over to NC 210 then follows NC 210 north to Spring Lake.

NC 87 extended through city

NC 87 swaps with NC 87-A

NC 87 rerouted to new US 301

NC 87 moved to NC 210

NC 87 moves back to NC 24

Fayetteville to Graham:
NC 87 was extended northwest of Fayetteville in 1940, replacing NC 24 through Spring Lake to Jonesboro Heights; duplexed with US 421 to Sanford, then multiplexed with US 15-501 north to Pittsboro, then replaced NC 93 from Pittsboro to Graham.

NC 24 Fayetteville to Jonesboro Heights

NC 87 replaces NC 24

NC 93 Pittsboro to Graham

NC 87 replaces NC 93

Between 1963-68, NC 87 was rerouted between Jonesboro Heights and Sanford onto its current routing, leaving behind Lee Ave and a snippet of NC 78.

NC 78 ending at Lee Ave

NC 78 extended east

Between 1954-57, NC 87 received bypasses around Pineview, Olivia and Swann - all in Harnett County, leaving "Old NC 87s" in its wake.
In 1970, NC 87 was moved off NC 24 and onto NC 210 south of Spring Lake.
In 1997, NC 87 was moved off NC 210 and onto NC 24 south of Spring Lake.
In 2000, NC 87 was rerouted to avoid Pittsboro, using new construction between US 15-501 and NC 902. NC 87 then duplexed with NC 902 to US 64.

NC 87 through Pittsboro

NC 87 bypasses Pittsboro

In Aug 2013 (NCDOT), NC 87 was placed on a bypass to the east of Sanford, along what had already opened as SR 9000 plus a little new construction. The piece between NC 87 Business and US 421 south of Sanford had been briefly contemplated as being US 421 CONN.
The substantial "Old NC 87" northwest of Pittsboro has never been NC 87. It was still NC 93 when it was bypassed.

Graham to Virginia:
The 1940 extension of NC 87 north continued from Graham through Reidsville and Leaksville-Spray (now Eden) into Virginia. This was a renumbering of NC 54.

NC 54 Graham to Virginia

NC 87 replaces NC 54

It is unclear if NC 87 used Wentworth St SR 1998 to leave Reidsville in its earliest days. NC 87 definitely is shown on Harrison on 1941 maps.
Before 1944, NC 87 was split into one-way alignments through Burlington. Westbound used the original NC 87 routing: Webb Ave, Front St to Trolinger. Eastbound NC 87 was added to the existing NC 100 routing: Trolinger to Davis St. which 87 followed back to Webb.
In 1949, NC 87 was rerouted to bypass Ossipee and Altamahaw in northwestern Alamance County, leaving behind SRs 1558 and 1569.
Between 1958-62, NC 87 was changed in Burlington to run two-way on Webb and Park. The entirety of NC 87 EB from before became secondary.

NC 87 on one-way splits

NC 87 consolidated

In 1961 or 1962, NC 87 was moved to its current routing from NC 65 to NC 770, leaving behind SR 2203 Ashley Loop Rd.
In 2000, NC 87 was removed from Reidsville. Up to then, NC 87 came in on Barnes St, then west on Harrison. Now, east of US 29, NC 87 cuts west over to US 29 Business, which NC 87 follows west around town to NC 65-87.

NC 87 in Reidsville

NC 87 avoiding central Reidville

Also in 2000, NC 87 was placed on a perimeter road around the south of Eden, then matched with NC 14 north around to the Virginia line. The old route through Eden is S. Hamilton St into central Eden; Stone Hwy east to Bridge St.; N Oakland Ave back to NC 14-87 (except used Meeks through Fairview)

NC 87 in Eden

NC 87 avoiding central Eden

In Aug 2014 (per Bob Malme), NC 24-87 was added to the new Outer Loop (future I-295) between Bragg Blvd and NC 210, to get NC 24-87 off of Bragg Blvd through the military base.
In Feb 2015, NC 87 was placed on newly constructed freeway around the east of Sanford. The old route through town is bannerless NC 87 while a BYPASS banner is on the freeway, along with some erroneous US 87 shields.

NC 87 through Sanford

NC 87 bypasses Sanford