Middletown, NY's Super-Interesting Old Downtown & Train Stations & the Intriguing Otisville Stop

I went to film my last 2 Metro-North West-of-Hudson Line train stations which I knew would be modern, and discovered two amazing old train stations in Middletown which, if the downtown was all fixed up, would be on the order of Charleston, South Carolina. One old, huge station is sadly in ruins but the other has been repurposed. Both are Romanesque gems from the 1890's. Otisville is a simple train stop but there is a lot of complexity around it, from the mile-long tunnel just outside of it towards Port Jervis, to the neighboring state and Federal prisons in town which you can't see from the main road, to an old, large, overgrown former tuberculosis sanitorium nearby. A lot to look at in one morning in Orange County, New York northwest of NYC.

[@erie910]

New York, Ontario, & Western. The Erie Railroad had a station, too, but moved commuter trains to its freight line which bypassed downtown.

[@Navilessor]

Live walking distance from the old O&W station. This particular line used to go through Sussex County , NJ and into Scranton, PA. The building was sold to a real estate developer in the late aught’s I think, he promised a lovely renewal at a town meeting (never delivered obviously). Then he kept not paying the taxes and finally the developer torched the place for insurance purposes. The last I heard he went to jail for nonpayment of taxes, who knows if he actually served any time. The second station was decommissioned in 1983, my husband rode that line on its last trip. It was turned into the library and it’s an absolutely lovely library. I’m glad you enjoyed my town 🙂

[@geo_walters]

I grew up there in the 70s and 80s. I remember when that train station was new, after they discontinued the rails going through the downtowns.

[@lesliemariee4335]

That’s the town, I grew up, Middletown

[@meampersandwill]

Love the vids Bill. Beautiful station, truly a shame that it's been condemned.

[@BillKing3456]

Totally agree, William (Bill?). Thanks for your comment.

[@Barb5001]

That video was taken this past (2022) summer. You can tell by the work being done on the down town side walks

[@jaygatz4335]

It looks as though there would have been a second track nearer to the canopy in Middletown.

[@BillKing3456]

@@jaygatz4335 could very well have been - that’s one thing I’ve noticed examining various old train stations is that there used to be more tracks back in the day

[@jeffnelson2930]

Thats Wall radio station at 11:03

[@guyfearful]

I use to do amazon deliveries in a step van here before they changed our routes. I know this town very well.
I can tell that the car has really destroyed towns like these. This is supposed to be a dense, walkable community with trains, busses, and streetcars. but instead its just another urban nightmare which is a pain in the ass to drive around in. So much unnecessary stress to go around in what should be a beutiful town with all the architecture.

[@BillKing3456]

Good comment.

[@iNFaMoUS_NY]

best way ive heard M.Town described hands down nicely done, i wasnt born here but moved here in the 90s from Queens, they are doing ALOT of work all over M.Town

[@donalddesnoo5303]

ow. Old woman or the old and weary it was known as

[@iNFaMoUS_NY]

The homeless gather at that old station, i really hope they get their act together when it comes to that O&W station

[@50pinkies67]

I lived in Middletown from 1977 to 1986. The very old O&W station was dilapidated during that time period too.

[@dmw1280]

I read there was a plan to fix the O&W Station?

[@BillKing3456]

That would be great, great news if true.

[@dmw1280]

@@BillKing3456 it’s only a rumor then the other rumor was plans to demolish. Who knows but it’s part of the historical mark to. Who knows ?

[@iworkout6912]

With the big fire, there were plans for the building, but of course the fire put an end to any plans.

[@tazironworker6019]

YES I HAVE A FIRE TUCK

[@jamesjacson]

I grew up in Middletown. It was much nicer back in the 70's. It's now a suberb of the city. Not nearly as nice.

[@aliciabishop4264]

SEEMS EMPTY LIKE A GHOST TOWN

[@BillKing3456]

Unfortunately, so many U.S. downtowns are way less vibrant than they were in yesteryear.

[@brooklyn7941]

That's Middletown for ya lived there for a while before I moved to Florida I'm from New York City wasn't like the city was much more quiet

[@erie910]

Not a good idea to trespass on railroad property.