I finished the East Village walk today and made it a couple blocks into the Lower East Side, going from E. 7th St. down to Rivington St.; about 8 miles.
The walk started across from Cooper Union, which is a college founded in 1859. Lincoln gave a famous speech here in 1860 and until last year it offered all of its students free tuition. Along the way I almost unknowingly passed by the former site of the Fillmore East theater (thanks rock and roll walking tour!), where one of my favorite Grateful Dead albums was recorded. As before, the blocks between Bowery and Ave. B are largely older walk-up apartments with some restaurants, bars and boutique stores at street-level. Between about Ave. B and Ave. D is a Puerto Rican neighborhood with a bunch of community gardens. East of Ave. D are the Jacob Riis Houses, public housing projects named for the famed tenement photographer and author of "How the Other Half Lives".
I kept walking for a couple blocks after going down Houston (pronouned "how-stun", not "hyoo-stun"), into the Lower East Side (or "LES"). I've heard that back in the day the East Village was considered a sub-neighborhood of the LES, but I think today it's generally considered to be the area east of Bowery between Houston to the north and Canal St. to the south (roughly).
Getting south of Houston is where this gets tough - you leave the numbered streets and avenues along with the nice grid-layout from the Commissioners' Plan of 1811. The Plan laid out the development of Manhattan north of 14th St. before it was heavily developed so that the rest of the island wouldn't evolve into a morass of streets strewn haphazardly at odd angles with no common naming convention.
So even though the Plan only really applies to the island north of 14th St., with the exception of the West Village, the area between 14th St. and Houston St. mostly adheres to some form of grid, which makes setting out a logical/efficient path easier for me.
Not quite ready for the chaos of Lower Manhattan, so I'll probably head back north for my next couple walks.