What is thickest gauge wire that can be inserted into Arduino headers?

Osgeld:
depends on voltage and how long you run it (heck "they" say you can run an amp though 30 gauge) ... though none of the parts on the arduino can sustain an amp for long

Only the wire insulation is a factor in it's maximum voltage rating, not it's current rating, which is only dependent on its gauge thickness regardless of the voltage used in a circuit.

Here is a current Vs gauge chart that might help the OP:

The following chart is a guideline of ampacity or copper wire current carrying capacity following the Handbook of Electronic Tables and Formulas for American Wire Gauge. As you might guess, the rated ampacities are just a rule of thumb. In careful engineering the voltage drop, insulation temperature limit, thickness, thermal conductivity, and air convection and temperature should all be taken into account. The Maximum Amps for Power Transmission uses the 700 circular mils per amp rule, which is very very conservative. The Maximum Amps for Chassis Wiring is also a conservative rating, but is meant for wiring in air, and not in a bundle. For short lengths of wire, such as is used in battery packs you should trade off the resistance and load with size, weight, and flexibility. NOTE: For installations that need to conform to the National Electrical Code, you must use their guidelines. Contact your local electrician to find out what is legal!

Lefty