Some (of Many) Old Buildings in Middletown, NY
September 2012
These are pictures of the old City of Middletown. When the railroad O&W (Ontario and Western) Railroad opened in 1868, many settlements along its route from New York City to Lake Ontario which borders with Canada boomed to become villages and towns.

But when O&W went bankrupt in 1957 (in no small part because of the proliferation of automobiles and interstate highways that superseded the railroad), many of the towns suffered. The City of Middletown endured because of its relative proximity to New York City. Many police officers and firefighters moved from New York City to Middletown to purchase houses that were less expensive.

The old City of Middletown is less than four miles from where we live. Although our mailing address says Middletown, our hamlet, Scotchtown, is actually in the Town of Wallkill. It confuses me to this day, but as long as the mail arrives, I'm not really complaining.

Click on a picture to enlarge.
Located on the corner of Railroad Avenue and Cottage Street, this building was a factory for footwear called Middletown Footwear in the 1930s. The building has long been unoccupied and it looks like it's being used today as a fish market until sold.
It's rusty and weathered but I'm guessing this mailbox by the old Middletown Footwear building is still in use. I'm thinking the U.S. Postal Service with offices and a big depot just a few blocks away would otherwise have removed it.
For ninety-five years since 1860, Clemson Brothers was the
The sign,
Victor Saw Works building on Railroad Avenue was part of the Clemson Brothers Saw company.
Intersection of two
St. Paul's United Methodist Church on East Main Street.
The local library ( has a photo of this building with the caption
This building, formerly Classy Leather Goods in the 1940s, is now Fort Knox Storage (where storage space may be rented on a monthly basis by homeowners lacking space to store their
In 1891, this building on Mulberry Street was a tannery. Today, it is owned by Classic Hosiery which manufactures women's stockings and children's tights.
There are many new establishments in Middletown, too. Like this
...and this hip hotdog joint called
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