All items shown in the photos are cast iron and were found within 10 feet of each other. The hex bolt heads have some red paint remaining on them. Pieces of an old carriage maybe? The old file is pretty cool as it appears to be hand made.
Carriage bolts have rounded heads, and the nuts are square. Red paint makes me think farm machinery --- International Harvester would be one that used red paint. Cast iron was used on stoves, but buggies, carriages and wagons were wood, and built as light as possible, because the motor was animals that pulled them.
This is a carriage bolt with a square nut. Any vintage buggy or wagon was built using square nuts, and if the bolt was not a carriage bolt it would also have a square head. I'm using this picture to show the square nut, the rounded part under the head makes it not an authentic vintage carriage bolt, see picture below.
This is a modern carriage bolt, but it shows how the head is built. It's rounded with square portion under the rounded head, which grabs the wood and holds the bolt while the nut is tightened. I've restored a couple of buggies, and it's really hard to find original carriage bolts anymore.