May 22-24, 2026. Last year the Vail Comedy Festival SOLD-OUT shows with 20+ comedians over Memorial Day Weekend for three days of laughs (watch video). Organized by the same team that has poured love into the Vail Comedy Show for 6+ years. The Vail Comedy Show is well known for hilarious, sold-out shows in a destination resort town, for which it has received international press coverage.