Speaking of Old Maps (because I was, below)...

You can access lots of great ones online. Trinidad doesn't appear on this 1792 map, but I did find Jamaica (kind of near Columbia Heights)and Mexico (appears to be between Georgetown and Foggy Bottom).

Looking around at some old maps that do show Trinidad you can see that the old B&O Railroad once ran down West Virginia Avenue and turned onto I Street. I think the route changed around 1907-8 when Union Station opened.  Here is a map of the current route. And that Graceland Cemetery that shows up where the CVS now sits? It was an integrated (but predominantly Black) cemetery founded in 1872. Starting in 1895 (the Federal Government closed the cemetery to future occupants in 1894) the more than 6,000 people buried there were disinterred and reburied across town at Woodlawn Cemetery. The process took three years. As for the race track that shows up north of Ivy City, I haven't got a clue.

Interesting side note:
Architect Daniel Burnham designed Union Station. His name will be familiar to any of you who read Erik Larsen's terrific book The Devil in the White City. Larsen's work tells the story of the 1893 World's Fair in Chicago. Burnham worked extensively on that project along with Landscape Architect Frederick Law Olmsted. Nearly thirty years before he took on work at the Fair Olmsted was in DC designing Kendall Green at what would later become Gallaudet University. Interesting, no? And here are some old photos of Gallaudet.