From left to right, top to bottom:
USA Enterprise Star Trek is… (Concept Artwork, 1964)
Spaceship Enterprise Star Trek is… (Concept Artwork, 1964)
U.S.S. Enterprise (Prototype) - 2243 and U.S.S. Enterprise NCC-1701 (Pre-Launch) - 2243 Star Trek: Final Frontier (Pocket Books, 1988)
U.S.S. Enterprise NX-0002 - 2242 Star Trek: Crew - “Shakedown” (IDW Publishing, 2009)
Enterprise The Star Trek (Lianhuanhua, Huacheng Publishing House, 1983)
U.S.S. Enterprise NCC-177 Mego Toys (Packaging Artwork, 1975)
U.S.S. Enterprise (“Space Academy” Variant) - 2257 Star Trek: The First Adventure (Concept Artwork, 1989)
U.S.S. Enterprise NCC-1701 (Smithsonian | Alt. Future) - 2254 | 2293 Star Trek: Early Voyages (Marvel Comics, 1997-1998)
U.S.S. Enterprise NCC-1701 - 2270 Star Trek: Planet of the Titans (Concept Artwork, 1976)
Enterprise Star Wars and Other Space Themes (Album Cover, 1978)
U.S.S. Enterprise NCC-1701 (Autobot) - 2270 Star Trek vs. Transformers - “Prime’s Directive, Part Three” (IDW Publishing, 2018)
U.S.S. Enterprise NCC-2813 (Kelvin Universe) - 2262 Star Trek/Green Lantern - “Spectrum War” (DC Comics, IDW Publishing, 2015)
U.S.S. Enterprise (Refit) - 2271 Star Trek: The Motion Picture, vol. 1, no. 1 (Marvel Comics, 1980)
U.S.S. Enterprise NCC-1701 (Phase II) - 2270s Star Trek: Waypoint (IDW Publishing, 2017)
U.S.S. Enterprise NCC-1701 (Alternate Kelvin) - c2259 Star Trek: Countdown to Darkness, No. 2 (IDW Publishing, 2013)
U.S.S. Enterprise NCC-1701-C - 2340s Star Trek: The Next Generation (Andrew Probert, Concept Artwork, 1987)
U.S.S. Enterprise NCC-1701-A - 2293 Star Trek: The Ashes of Eden (DC Comics, 1995)
U.S.S. Enterprise NCC-1701-E - 2387 Star Trek: Coda - “Moments Asunder” (Pocket Books, 2021)
U.S.S. Enterprise NCC-1701 (Kelvin Universe) - 2261 Star Trek: Parallel Lives, Part 2 (IDW Publishing, 2014)
I.S.S. Enterprise (Kelvin Mirror Universe) - 2263 Star Trek: Live Evil, no. 2 (IDW Publishing, 2015)
The various renderings of ships in the image were crafted by the Roddenberry Archive team to represent some of the myriad Enterprises that have been featured in various beta-canon works from novel covers to comic books, unused concept art, and more.