Cool thread Michael. Love to see old iron. I inherited and refurbished several old tools many years ago. Still using a 1954 Delta/Rockwell 14" bandsaw and 1952 DP-220 drill press and both perform well. But my oldest tool is this 1951 DeWalt GW-4 RAS. Rock solid and accurate.
I love this old sander! It's a Porter Cable Speedmatic 503. I have no idea when it was made, but it was my father's, and I can remember him using it back in the 50's. It is a beast, very heavy, and is the only portable belt sander in my shop. It uses 3 x 24 belts and still runs like a top.
Old Craftsman drill with an attachment that will drill perfectly perpendicular holes, sort of like a portable drill press! This belonged to my dad, and I still use it. Can't remember how old it is but it has a plate with model number 315.11090 that I can probly research.
This is a 19th century lathe that I bought from Al LeCoff over 30 years ago. I recently remade the wooden bed (using the heart pine bed timbers that came with it). It most likely ran off a line shaft at one time: I put a 2 hp 3 phase motor with vfd on it. It has babbitt bearings in the head stock: I put ball bearing pillow blocks on the jack shaft. This is the lathe I use most in my shop.
This is a topic that is relevant to my interests! Most of my power tools are older than I am by a considerable amount, and I have gotten bitten by the find/rescue/restore/use bug.
My oldest wood working power tool is this 1939/1940 Delta 6" Jointer:
My overall oldest working power tool is this 1928 South Bend Junior 9" lathe, which came with the original overhead shaft transmission. I have set it up to run off of a 1HP DC variable speed setup.
Other much newer but still old, and honorable mentions:
~1967 Rockwell/Delta "6+6" drill press
~1953 Craftsman 10" table saw, been in the family forever:
1963 Rockwell/Delta 14" wood/metal bandsaw:
Old Craftsman/Dunlap 103.23100 drill press, probably just after WWII:
Here my oldest verifiable machine. A 1940 Delta DP-220 14" drill press I tricked out with a DC motor and a few other things. Probably the oldest machine I use is a Millbury single end tenoner I think was made before WWII, but I can't verify that.
I'm not much of a scroller, but when the need arises, this is the tool I use. Based on the serial number, I believe it is a 1964 model 40-440. It may be old, but it runs like a champ. More than I can say for the owner.
I love those Delta 40-440 scroll saws also. I've currently got four that I've restored, but use only one of them on a regular basis. It was an early 1970s model when I got it. I'll use it for some little thing or another at least once a week.
Probably the oldest I own. Darra-James (Montgomery Ward house brand) jointer. I am not the original owner and this one, as far as I know, is a 1950's model. Interestingly, they stopped manufacture in the 70's or 80's, went pretty much out of business but have a web page and still sell parts from left over inventory 3 days a week.
You probably don't want to see how it joints fingers!
My oldest power tool would be a Diehl 55, dated 1948. Age verified by the head of Diehl, who wanted to come by and see it several years ago. He said they liked to keep track of them. He said only models prior to 1950 had cast iron bases, who knew?
Just as an after thought. This saw will straight line 16/4(4") material