Currently updating as part of a site revamp.
Before 1940: As far as we know, this was an unnamed county road (it probably had a number) going from Highway 6 (Wellborn Road) to S. Holik Farm (the border of which is now Glade) (internal link)
1949: "The Knoll" planned out, and built by 1955.
1960s: County Road renamed to Holleman.
1970s: The road builds an extension from Winding Road (where it had previously curved into), re-routing west from its straight-away connection, and going to the modern day Texas Avenue, as well as a little bit past modern-day Lassie.
1972: Pooh's Park opens on the north-of-Texas-Avenue side (source: clipping)
Late 1970s: Tinley's Chicken 'n Rolls opens near Pooh's Park (though their website mentions a 1968 Tinsley's opening?)
Late 1970s or early 1980s: Holleman Drive West opens (likely opened under a different name, though I can't confirm or deny that) and builds its first duplexes along the road. Meanwhile, "Sutton Place" builds off the bypass with several residential lots facing south. None are developed. This why Holleman bends a little toward the highway, it's the old Sutton Place road.
Late 1982/early 1983: Holleman extends to the new bypass to provide access to Post Oak Mall. As a whole, this section is Holleman Drive East (and does not have striping)
Mid 1980s to Late 1980s: Holleman Drive West crosses the railroad (ultimately resulting in the closure of the Luther Street crossing)
1990s: A shopping center (Plantation Shopping Center) builds at the corner of Holleman and Texas Avenue in the early 1990s. Over the years, this would include H-E-B Pantry, then Target, then Hastings (circa 1997), then finally Old Navy (circa 1999)
March 2002: H-E-B opens at the corner of Texas Avenue and Holleman. The new store is much bigger than the Pantry it replaced. The old Pantry is replaced by Gattitown a few years later.
1996: A stoplight is funded for Anderson and Holleman. [source]
Late 1990s: A four way stop is built at Welsh and Holleman, near the Checkers gas station. The eastbound Holleman stop sign is affixed to a metal power pole.
Early 2000s: The Glade stoplight opened. This replaced a four-way blinking light, suspended by four wires, creating an "X" over the intersection. I kind of miss it. Also, in this era (though a few years later) was the Dartmouth stoplight (replaced stop signs) though the area continued to be undeveloped for several years.
November 2004: A road opens from North Dowling Road to Rock Prairie Road W., incorporating part of Abbate. This is called "Jones-Butler Road", in anticipation that it would connect to the Jones-Butler on Holleman.
December 2004: A gas station opens at Harvey Mitchell and Holleman, featuring Rattler's convenience store and Wendy's, as well as a dry cleaners. Subway comes later.
2005: At about this time, Lincoln Center adds on a new addition.
2006: Previously, in the "main stretch" of Holleman, there were four lanes (no left hand turns) from Wellborn to Eleanor (the rest was two lanes with a turn lane and shoulders). In 2006, this is reduced to the four lanes stopping at Oney Hervey. This allows better left-hand turns into Arizona and Oney Hervey. Also, Marion Pugh extends to Holleman.
2007: Holleman opens a stoplight at Harvey Mitchell.
2008: A right-turn yield lane to Harvey Mitchell is added.
2008-2009: At about this time, a four-way stop sign is added near the Lincoln Center. Also, the Lofts at Wolf Pen Creek open, featuring Red Mango, Honeybaked Ham & Deli, and Tutta Pasta. Within a few years, all of these but Red Mango are closed.
Late Summer 2010: Jones-Butler (between North Dowling and Rock Prairie) renames to Holleman Drive South (as well as I-GN between Rock Prairie and North Graham), as Holleman prepares to extend. Around this time, Saddle extends to Holleman.
Spring 2011: Holleman finally finishes its extension to North Dowling. It's four lanes and concrete. The section between North Dowling and Saddle closes for reconstruction.
Summer 2011: The reconstructed area opens, creating a solid Holleman Drive that goes from the mall to North Graham Road. The Cottages of College Station begins construction.
Spring 2012: Deacon Drive builds a small stub off of Holleman Drive South but goes nowhere. It is a nice two lanes + turn lane + bike lanes + sidewalk concrete road with eventual connections into the Barracks. There is a turn lane on Holleman in this area. Despite the speed limit temporarily lowered to 45 MPH during construction, it goes back up to 60 MPH soon after.
Fall 2012: Maroon U opens in the old CC Creations spot.
HOLLEMAN DRIVE WEST
Originally a small stub extending from the "West Loop" with a few duplexes on it, Holleman expanded with the Woodway duplex subdivision and Woodway Park, with the connection to Holleman completed in late 1985.
HOLLEMAN DRIVE SOUTH
Originally, as a result from the abandonment of the I&GN railroad, there were two generally unimproved roads: "I&GN Road", which stretched from Straub to Gandy (it curved east to Gandy), and another unnamed road (which had the tar-and-gravel mix in the 1990s at least) from FM 2818 (it wasn't Harvey Mitchell Parkway at the time) to North Dowling Road. In the late 1990s, this unnamed stretch was renamed as Marion Pugh in preparation to connect to the Marion Pugh segment north of Holleman. However, plans changed (partially because some of the ROW was already bought), and when a new, paved and flattened (at 60 MPH) road that opened in November 2004, Jones-Butler Road, Marion Pugh was soon renamed to Jones-Butler Road after being repaved. The new Jones-Butler Road (with a full four-way stop at North Dowling within less than a year) connected North Dowling Road to Rock Prairie Road. Frustratingly, not too long after Jones-Butler opened, the entire intersection was closed due to culvert installation, forcing cars all the way down to Cain or Rock Prairie, and the construction left a bumpy patch where it had been nicely done less than a year prior.
As the years went on, another segment of Jones-Butler opened, this time connecting Harvey Mitchell Parkway up to where Jones-Butler terminated at Harvey Mitchell Parkway, a right-in-right-out thing. This was originally supposed to go under 2818 when they built the overpass, but TxDOT didn't want to do a longer viaduct and ended up justing cutting it off, so a third plan was formulated. This time, Holleman would curve into the existing Jones-Butler, but due to some land swap issues, wasn't even started until after the FM 2818 overpass project had been completed, forcing the old Jones-Butler segment north of 2818 to be dead-ended, and the south part to be right-in-right-out. North Dowling Road at Harvey Mitchell was also closed.
In 2010, the segment north of Dowling was "de-named" (now just a detour route) with Holleman Drive South being the name adopted for the road between North Graham and North Dowling (part of I&GN had been improved around 2005). Saddle Lane was also extended and repaved in preparation for the detour. In 2011, soon before the overpass completely finished up, Holleman Drive South opened, with many stubs (red barricades with "Road Closed" signs, these were taken down when the Cottages of College Station began construction). Phase One of the detour involved the former Jones-Butler being cut off at Saddle with cars forced to abruptly make a left turn and wind through Quail Run. By 2011, all this was sorted out, though a few things changed: the fall 2012 of the Cottages of College Station (lots of traffic) and the slight, cheap expansion of Holleman at Deacon Drive West in Spring 2012.