A dilation system includes a balloon catheter and a puncturing assembly. The balloon catheter includes a shaft, a dilator coupled to a distal end of the shaft, and a lumen extending through the shaft and the dilator. The dilator is expandable from a collapsed state to an expanded state. The puncturing assembly includes at least one cutting member. The puncturing assembly is positionable within the lumen of the balloon catheter or along an exterior of the shaft when the puncturing assembly is in a first position. The puncturing assembly transitions to a second position to puncture the lumen of the balloon catheter and/or to puncture the dilator, to thereby drain fluid from the dilator.