I have a cymbal that is supposedly from the 1930's. There is only 1 piece of info on the internet about it that hasn't come directly from a post here I made about it. The cymbal is stamped EL RAJAH (not the same Rajah from the 60's, this much I know), has 24 rivet holes, and is 20". The thing sounds gorgeous. The rest of my gear is somewhere between 35-50 years old, minus a pedal, throne, and a stand.
My oldest gear is a Zildjian 20" Very very light crash-ride, Its 1660 grams, When used as a ride it sounds like a tad brighter version of a 22" K Light, and when crashed its a beaut, I use it as a crash, Its from the late 50's early 60's so WAY older then me.
My Ludwig Standards date from the early 70's, but I used to own a Ludwig Pioneer snare (with original heads) that was at least 1965, and an MIJ stencil kit of about the same age. I'd love to score another Ludwig vintage kit someday, but not just yet.
My oldest piece of gear is me. A 1950s model. Timeless in form and function. A "classic" but not an "oldie".
Seriously, I think it's a late 1970s Zildjian 20" Pang and the Tama boom stand that I bought to support it. I have a trap case and some mics/stands from around the same time. A favorite is my AKG D202 (1976?). Heck, now that I think about it, I believe that my old four track reel-to-reel (Dokorder 7140) is on a shelf in the basement. And it occurs to me that I still use my Klipsch Heresy monitors daily, and I bought those around 1977-78.
Probably my oldest is a 1920s Ludwig Deluxe (commonly referred to as a Black Beauty.) I have a handful of others dating from that era into '40s including a lovely Ludwig & Ludwig Victory Outfit. I imagine I have a few cymbals from the '30s, but most are '40s and newer with an emphasis on '50/'60s Zildjians.
The oldest gear that I actually use is a c1959 Ludwig transition badge kit with its original Playon plastic heads, and I only use it to record with Rip Masters, who's as particular about drum sounds as I am.