Walking Riverside Drive, A “The City I love” project Part 1: Uptown Beginings

The Project

The goal is to walk the entire length of Riverside Drive where possible from Inwood down to the Upper West Side. I’ll try to average one mile per day and try to write or document via photos what I see along the way. Riverside Drive has a very diverse history and exploring it from stem to stern sounds like a fun project. After all, if The New York Times could do it why not me?

The reason why I decided to start from the north and not the south is to in order to get the trickiest part, which is the highway sections out of the way. Also as you head south the Drive gets progressively wealthy as you go along so you get a chance to notice the change in subtle ways. If you choose to head from North to South you may also notice that you are going back in time with much of the northern section predominately 1920-s 1930’s to the southern half which is more late 1800’s inspired. Also Riverside Drive is one of the least altered streets in Manhattan so it will be easier to notice the difference as you walk from one end to the other. If you choose to do this project you don’t have to do all but pick parts of the drive to explore on your own.

So let’s begin.



Riverside Drive during the 1910’s Photo by The American Art Publishing Co.

If Park, Madison, and Fifth Avenue are to the east side of Manhattan island in terms of New York City’s upper crust, then its west side counter parts should include Riverside Drive. A street with a colorful history, with railroad barons, gilded age mansions, trophy wives and of course the ‘Master Builder’ Robert Moses. A man which no neighborhood of this great metropolis was spared, for better or worse from his influence.

Riverside Drive, a byproduct of the creation of Riverside Park is one of the city’s most scenic areas that is often overlooked compared to its flashier neighbor to the east, Central Park. Riverside Park and Riverside Drive were started in the late 19th century as part of the development of the West Side of Manhattan. For much of the 19th century, the area was a hodgepodge of estates, industry and small villages clustered along the Hudson River.

That all changed when Fredrick Law Olmstead, the creator of Central Park was given 191 acres to play with to create a new park in 1872. Essential to the design was the Drive which Olmstead merged with the park plan to create one singular project between the two. Olmstead’s former collaborator, Calvert Vaux did the landscaping for much of the first half of the project. While much of the land was acquired by condemnation, the Hudson River Railroad now acquired by the New York Central  Railroad would remain in place, while the park was developed around it. The first sections of Riverside Drive opened in 1880 and was completed five years later.

In 1911, Riverside Drive was extended further uptown to Audubon Park, now today known as Audubon Terrace with a series of viaducts, the most famous one being just north of Grant’s Tomb.  With the extension, Riverside Drive absorbed Boulevard Lafayette. A planned road from Audubon Park.  Longtime residents, the Grinnell family used their political connections to connect the two roads in order to boost their property values. Which creates a triangle-shaped aberration in the city’s grid.

In fact much of how the park that we see today was given to us was actually by Robert Moses under the West Side Improvement project.  The project, which were the cost of two Hoover Dams, included the grade separation of the railroad and the Henry Hudson Parkway. Perhaps most importantly it practically buried the railroad and created a man-made hill that covers the tracks that is with today. However it should be noted that the Parkway also in certain areas isolates both the park and drive from each other and I will try to document where that has happened.

Part 1: From Dyckman Street to Plaza Lafayette.  


Tiled mosaic of the Dyckman-200th Street Station

So on a mild Friday afternoon, I set off from my apartment in Washington Heights to the subway to Dyckman Street which is the northern terminus of Riverside Drive. The last address is 1825 Riverside Drive, which reminded me of the Flatiron Building downtown. Opposite the apartment buildings is Fort Tyron Park, which today is home to the Cloisters, an outpost of the Metropolitan Museum of Art.


1825 Riverside Drive, the last building on the Drive

On the next block, Riverside Drive merges with the Henry Hudson Parkway, so to continue I returned to Dyckman Street and towards the Hudson River. Once your turn left you will see three bridges. The first, is a concrete arch bridge that instantly reminded me of the art-deco bridges in California. Originally when the Parkway was a four-lane highway, it carried bi-directional traffic. When it was expanded, a second but lower bridge was added. The last bridge is the old Hudson River Railroad which were acquired by the New York Central in the late 1800’s. Today the tracks are now under the use of Amtrak. Its bridges is the lowest of the three. It’s between the latter two bridges that access to the greenway can be found.



The Bridges over Dyckman Street

So for the next mile or so I walked the greenway, with the cars roaring to go upstate on my left and a low stone wall to my right. The path narrow due to the fact that leaves covered up most of the right side of the pathway. So much for staying on that side. Luckily, they weren’t many joggers or bicyclists on the path but I constantly looked behind me, the reason being the road bends a few times so it made sense just to be cautious. The Cloisters came into view and then disappeared under the trees as I headed further south. The park has a massive arch bridge that leads to the Cloisters, the bridge was probably created so that people driving from the parkway can access the museum.


Cloisters approach and bridge

Further down, there is a massive collection of arches made out of Maine granite situated near the southern end of the park. It is all that left of the grand Billings estate. It served as the driveway to the home, formerly owned by Charles Kingsley Garrison Billings. The driveway alone cost $250,000 and the rest of the house was so grand it would put even the Rockefellers to shame. Sadly, Billings, an avid horseman, grew tired of the house, and sold it to interestingly enough the Rockefellers. Almost immediately, the Rockefellers wanted to give the land to the city and tear down the house. However, lovers of the home and its architecture spared its demolition but not from the laws of nature. In 1925 the house burned to the ground, the Rockefellers again offered the land to the city and this time the city accepted. In 1939 the Cloisters Museum, which was given to the city by John D. Rockefeller Jr. opened to the public. Today only the driveway and lawn of the Estate remains however the driveway is largely cutoff from the park.


Billings private driveway cars probably drove up to 15 m.p.h. back in the day now cars zoom by at 60, missing the grandeur of years pat.

Not long after seeing the driveway, the lush and parklike aspect of the area gives way to apartments that overlook the river. Also nearby is Inspiration Point, a lookout stop that was designed for motorists to stop, take a break and admire the scenery. Here’s an excerpt from a New York Times article in 1989 discussing the characteristics of the structure.


Part of the Inspiration Point lookout.

“A two-way drive, it had a wide sidewalk on the river side; this was an environment where the automobile and the pedestrian were meant to mix agreeably. Drivers were encouraged to stop at the roadside in a large turnoff in front of the $150,000 shelter, the last stopping place before the end of the drive at Dyckman Street.”


View of the GWB from lookout

However, shortly after the completion of the shelter Robert Moses’s planned West Side Improvement project doomed the shelter and it now today, the shelter is now slowly crumbling to nature. 27 years later some things have changed, but it still has the feel of a “picturesque ruin,” as detailed further in the article.

“As the automobile changed from a pleasure vehicle to mere transportation, the pleasure drive lost its patron in road planners. The Miller Elevated Highway (or West Side Highway) below 72d Street of 1931 to 1933 was meant for moving, not inspiring, people. But it was Robert Moses’ Henry Hudson Parkway of 1937 – although an idyll compared to the modern interstate – that made the bed of the old isolated Riverside Drive a through highway, with a bridge crossing the Harlem River.

GRADUALLY, increased traffic turned what had been a walking/driving experience into a no man’s land for pedestrians. The walkway is now overgrown and concrete bumpers now barricade what was the original promenade.

The shelter at Inspiration Point itself now suggests despair. The doors to the toilets are walled up. Cast-stone copings, indeed whole sections of balustrade, have been pushed over, down the steep slope. The rotting wooden roof has miraculously escaped destruction by fire, but whole sections have fallen off or hang precariously at the edge. Water damage has buckled the elegant coffered ceiling and most of what remains looks like driftwood scavanged from a lost civilization.”



Plaque dedicating the ‘Improvement’ to Riverside Drive, little did they know…


Up above are art deco apartment buildings built in the 1920’s before the stock market crashed. Also overlooking everything there is a house actually perched over the retaining wall! I wonder how much the insurance is going to cost if the thing falls over.


No explanation here

The final landmarks that come into view are the George Washington Bridge on the right and the Castle Village apartment complex on the left. The complex, which features five cruciform towers were the basis of the ‘towers in the park’ concept of modernist architecture. The concept was widely reproduced in many of New York City’s housing developments both public and private during the postwar era. Its social effects are still being felt today.


Castle Village apartments. Completed in the mid 1930’s these apartments were meant to be shelters for Manhattan’s middle class residents back in the day. The more things change the more things stay the same I guess.


In 2005 the retaining wall, dividing the property and the ramp leading down to the Parkway collapsed. No one was hurt and the wall was repaired. Today you can see the distinctions between the replacement wall and the original. When I passed by, no vehicles were parked there. However, I think if you’re going to park a car along that wall, it might be the safest place to do so.


The Castle Village retaining wall the original section is to the right.

The footbridge leads me to Plaza Lafayette and the end of part 1 of the trip. I’ll save the Bridge photos for part 2 of the project. I will continue further south, pass through more Art-Deco structures, see parts of abandoned Riverside Drive access points and deal with that pesky triangle.  Also follow on Instagram with the #WalkRvierside to track my progress.