A Winchester 1894 made in about 1912. Lots of nicks and wear but still shoots as good as ever. It was a wedding gift from my great-grandfather to his new son-in-law, my paternal grandfather.
Next oldest is my Dad's first rifle, a 1930ish Savage .30-06 Sporter (I think that is a Medel 40 or something). It was bought at a local hardware store in 1935 for $35 (those were the days!). I had to have it restocked as it cracked badly behind the single column mag well, and the safety spring broke so that was fixed. Now it shoots great as ever, very accurate. I happened to see the same model at the gun show yesterday for $700! ridiculous.