An antique map of my imagining of Pre-Classical Equestria, showing things as they are at the beginning of my fan-fiction, The Tale of Two Sisters. Based on the latest official Equestria map, this parchment was drawn in a Tolkin-esque style to evoke a simpler time, featuring archaic spellings and various locations not officially placed!
Feel free to download for the full size and use for any Pre-Classical era roleplays, to give your players the lay of the land. At a later date I will draw a Post-Classical map to reflect the events of the story.

Some bonus information about this map you might like to know:

The Crystal Spire is a recently reclaimed ruin; having once belonged to the Crystal Empire under the rule of Queen Amore, the Empire collapsed many moons ago, leaving only the large crystal tower at its centre. The building was captured by Canterlot's forces during the Great Griffon War to defend the Yak front, lead by Commander Sobra, who was awarded the region for his heroics. With his newfound Dukedom in a post-war world, Sobra named the building and began settling the area.
Sombra would later become corrupted by a strange crystal found in the Spire, enslaving those who had come to live in his land and becoming a threat to Equestria himself.

The Ruins of New Canterlot were once a budding offshoot of the capitol, turned to a defensive point against the Changlings during the Great Griffon War. Despite the eventual victory, New Canterlot itself was decimated by enemy forces, leaving it nothing but rubble.

While marked as a "Hippogryph Effigy", this is in fact a massive statue of a seapony. As contact with the hippogryphs has been limited and cold at best, the origin or meaning of the statue is unknown to ponies.

While the existence of Kirin has been noted by pegasi explorers, actual contact has not been made and sightings are rare. While a tribe is known to live on the south-eastern island, their settlements or numbers are unknown.

The Windigo Wastes in the South are named after the Hearth's Warming tale, with the creatures being said to have turned the southern cap of the world into their own frozen wasteland, where they live to this day. Be it from danger or superstition, no pony has dared to explore that far south to found out.

The Kluuj people (a race of fish- and reptilian-like anthropods) began as a half-land, half-sea town on the southern shore of Equestia, only travelling North to run a large marketplace just north of the Cloud Ridge Mountains, trading with any creature without prejudice, as long as they have the coin.
With the success of their race-blind trade-based economy, the Kluuj people eventually moved north to settle the marketplace itself, given that transporting rarer cargo in by airship was more profitable than fishing and handmade seaside trinkets. Their name was later corrected with the naming of their new city, Klugetown.

The airspace South of South Sea Port is known for an abundance of Sky Pirates, known for pirating sea and airships alike, to and from the Kluuj market, particularly those to the West coming from Abyssia—another reason that pegasi expeditions have not travelled too far South.

Built in the natural bottleneck of the Macintosh Hills, Fort Macintosh was the front line against the coordinated Diamond Dog invasion during the war, and was ultimately successful in its purpose. Ironhide, a war hero from this station, was promoted to Commander of the Valkyries on his return to Canterlot.

The South-East of the map would have an arrow pointing towards Saddle Arabia, if the two nations had made contact at this point, which they have not.

Edit: Fixed some unerased parts and improved some shapes of the border.
Edit 2: Fixed accidentally leaving the background opaque.
Edit 3 (11/09/20): Added the absent Fort Macintosh to the map; removed the western "Mount Everhoof" and renamed "Mount Olympus", as I discovered an official map had already named it as such; renamed the "Crystal Outpost" to "Crystal Spire", because if the map was updated to show the ruins of New Canterlot, it should have reflected this change as well, as well as labelling it as an annex; minor alterations to some landscaping for biome clarity; added arrow to Neighjing, which was more recently added to head-canon, as well as a marker for the comic-canon Forest of Leota; also added additional lore to the description for anyone who is interested.