Rifle - GEW 88 made in 1890 with 1914 Depot approval stamps and Turkish markings.
Pistol - S&W model 1 1/2, August of 1887 tied with Marlin topbreak .38 S&W revolver made in 1887.
Shotgun - my great grandfather's 12 ga side by side muzzle loader, circa 1845. He carried it from Ducktown, Tn to what is now NW Arkansas in 1848/49 and on to west central Missouri in 1852.
I have loaded, special light loads, for both revolvers and fired them, once. I have never fired the rifle (no desire to) or loaded the BP shotgun but my dad used it for duck hunting when he was a kid (late 20s and 30s).