Head bolt leaking

For the past 3-4 weeks one of my head bolts has been leaking antifreeze. I am sure it's the head bolt and not a hose or something because after I shut my car off and look under the hood I can see the coolant slowly coming up around the bolt. The bolt that is leaking is the middle one right next to the carb. I took the bolt out and put silicone around the threads and torque it down. That seemed to help but it still leaks. Can I put silicone all around the bolt head or should I take the bolt back out and put silicone all over the shaft and head of the bolt? Also, the cylinder directly across from the leaky bolt (third one back from the front) is leaking a little oil because I can see it in the spark plug area and it fouls that plug. I don't think it's the valve cover gasket because I've replaced it twice and put silicone on top and bottom of the gasket. My dad said there could be a crack in the head since it's leaking directly across from eack other. What do you guys think?

It could be a cracked head but I think it's more likely it's a bad head gasket. Torquing the bolts down will help some, but if the gasket is bad it will need to be replaced.

If it was the head gasket wouldn't it be leaking around the outer edge of the head and not up the head bolt? Could I put silicone around the bolt for a temporary fix?

silicone won't hold up to the presure of a cracked head or a bad head gasket. It sounds like your going to need to pull the head to get to the bottom of the problem. If you go with your temporary fix, Torque the bolt to spec, no more.

I went in my garage and looked at a spare head gasket that I had laying around and I have to admit that it looks like it would be pretty difficult for coolant to make it's way from the cooling passage to the head bolt hole without also getting into the pushrod (crankcase) cavity. Are you seeing any indication of coolant in the oil as well? Any foaming, thickening, or chocolate brown coloring in the oil? If not, I'd be leaning towards diagnosing a crack, but it's true you are still going to have to take the head off to figure out for sure what's going on.