The photo above is from Mike Traverse's personal sign collection. The shield may be ugly, but the sign sure is old.
US 209 SB and US 6 WB, riding together into Pennsylvania over this old steel deck bridge.
The other direction in 1972, courtesy Michael Summa. Two changes from then to now: the city name signs are gone, as is button copy.
Still SB/WB on the duplex, underneath first Front Street and then (obviously) the former Erie Railroad, in Port Jervis. The reason the railroad overpass is so long is that the rail yard just to the northwest used to be even more sizable, and sent several more tracks over Pike Street (US 6/209) than it does now.
Closeup of the sign on the overpass, which neglects US 6.
Like the other black and white photo, NB in 1972 courtesy Michael Summa. The strange US 209 shields are clearly from one certain time period, maybe the late 1960's after the "US" dropped out of the shield.
Various old historical signs, all northbound, and yes the second one is every bit as legit as the other two. I believe it's a style that was briefly tried out and then abandoned, because there are a few of them but other signs both older and newer return to the squarish look. I left the blurry photo in because it's of the New Jersey claim line, which is an awesome bit of hsitory to consider (NJ wanted about another 5-10 miles of New York west of the Hudson).
Across the old, into the wrong. The last one is in Wurtsboro just north of former NY 17; I know this because apparently there is only one Pine Street intersecting any of US 209, at least according to Google Maps.
In the haste to send out all those state-name shields at once, I neglected this beautimous aged NB curve sign, with the extra-large old-style advisory speed. 1960's if you're unlucky, 1950's if you're lucky.
As you can see from the text at the bottom, the state again erected this one, but this time it was the Education and Conservation Commission. This 1935 sign is not only unique for having beavers on it, it's also green! Find it at Summitville Road in the town of the same name.
Herlings Road is a tiny dead-end, but for whatever reason it gets a fifty-year old painted sign. Click for rainbow closeup and you won't be disappointed.
More old, more incorrect, all northbound.
The oldest of the old, possibly the last red warning sign diamond left in the state. These wooden diamonds were erected in the 1950s to draw more attention to dangerous things like sharp curves. It's near Spring Glen - I won't say anything more because I don't know specifically where it is, and this photo is courtesy John Krakoff.
An old alignment of US 209/NY 55 NB/EB, Old Queens Highway, veers off Turkey Hill Rd. into the underbrush and disappears.
Old Queens Hwy. returns from the underbrush and veers back into 209/55. Last photo looks back southward.
Heck, because I love you, have a few more old northbound signs, on the house, including two versions of the NY 55 split because I love you THAT MUCH (or because the older one came out better, but the newer one has a RIDOT-esque county shield). Sorry, if I actually loved you THAT MUCH I wouldn't force-feed you non-cutout shields. That Bevier sign reads like a poem, don'it? Ulster CR 6 is Kyserike Road; several counties such as Orange issue new diamond county shields with the county outline inside, but Ulster has since gone to the traditional pentagons, leaving these signs rare, especially along a major state highway. Like too many shields in southern NJ, this one has the 6 patched over some other number, or else patched onto a blank.
Right around that old speed limit sign, NY 213 jumps onto US 209 and back off again, but another smelly detour lingers. (Note that it's 213 WB that multiplexes with 209 NB, but the detour is for EB, which is entirely reasonable.) I prefer US/state errors to non-cutout errors.
Ulster CR 29, former US 209, SB in Hurley crossing modern US 209 as it heads to the church.
The last hurrah for this page, one last bit of button copy on US 209; there's more on NY 28, but none left on 209 otherwise. This sign is still on an undivided, unrestricted-access part of US 209, but it soon divides into the Kingston-Rhinecliff Bridge approach, where it ends at US 9W and turns into NY 199.