High Bridge is 175 years old. And, after a restoration a few years back, looking great. It was built to carry the Croton Aqueduct from the mainland into Manhattan, over the Harlem River, and it’s been a pedestrian path as well for most of its life.
The picture above shows the bridge (and the aqueduct pressurization tower) circa 1900, when the bridge was younger than I am now. The river arches were replaced by a steel arch in the 1920s, to improve navigation on the Harlem, which is unfortunate but too late to address now.