We demonstrate large nonlinear terahertz responses in the gaps of metamaterial split ring resonators in several materials and use nonlinear THz transmission and THz-pump/THz-probe spectroscopy to study the nonlinear responses and dynamics. We use the field enhancement in the SRR gaps to initiate high-field phenomena at lower incident fields. In vanadium dioxide, we drive the insulator-to-metal phase transition with high-field THz radiation. The film conductivity increases by over two orders of magnitude and the phase transition occurs on a several picosecond timescale. In gallium arsenide, we observe high-field transport phenomena, including mobility saturation and impact ionization. The carrier density increases by up to ten orders of magnitude at high fields. At the highest fields, we demonstrate THz-induced damage in both vanadium dioxide and gallium arsenide.