I've got an outside gazebo with electricity running to it. In the gazebo I have power to the TV/DirecTV box, 2 lights, and ceiling fan. Every time I get a good rain, the breaker for that power trips. After I reset it, I am only able to turn on the 2 lights and TV/DirecTV box. When I attempt to turn on the fan, the breaker trips again. The fan most likely draws more power as it's pretty big. I know something is getting wet but I don't understand why 2 of the powered devices will not trip it but one will. Also, how do I find what/where is getting wet during this rain? The breaker is in this behavior for a few days after the good rain until what I can only guess it dries out wherever it got wet. Any ideas?

Is roof completely covered ? Or like a pergola with slats on top ? Unless it's some kind of crazy fan it shouldn't be pulling much over 2 amps when on.
Is this on a gfci circuit ?

Also is there an exterior junction / outlet box that is exposed to the elements ?

Had a similar problem at our old house for years with our deck lighting and convenience outlets. The GFCI for the circuit was located in the service panel. When we were selling the house, the inspector wrote up the wiring to the lights on the deck were exposed and needed to be in conduit. So I purchased conduit and was installing it when I noticed a junction box under the deck.

Turned out that the junction box had the wires enter the top of the box and had some caulk over the wires entering it, but is was not properly sealed so whenever it rained quite a bit water entered the box. The wires were not properly twisted together before the wire nuts were installed so there were weak connections as well. When I rewired and properly sealed the JB, everything worked great and saved me a bunch of bucks not having to replace the GFCI breaker.

So, maybe something to look for in your case...

got any other outdoor receptacles in that circuit?

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got any other outdoor receptacles in that circuit?

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Unfortunately on the same circuit I have several landscaping flood lights in the trees. Some are 30-40 feet up in the trees.

I had same issue with pool pergola. When eletricians pulled wires they skinned one. They pulled new wire to solve my issue.

Thought this was going to be about eating mushrooms in the woods.

maybe a squirrel has caused an issue so that rain can get in