June 2–5 Break out the bike shorts (and oxygen mask?) for the Mt Hood Cycling Classic, a high-altitude challenge for various ability levels. Registration ends May 31, but spectators can watch riders tackle savage climbs, straightaway sprints, and 180-degree turns. mthoodcyclingclassic.com

June 8–12 Ten US Navy, Coast Guard, and Canadian Maritime Forces vessels dock along the waterfront during the Rose Festival’s Fleet Week. While adorable sailors wander downtown, their ships are open to visitors for free tours. rosefestival.org

June 13 Pulitzer Prize–winning New York Times columnist and Oregon native Nicholas Kristof presents “Revolution in the Middle East: What Next?” at the Arlene Schnitzer Concert Hall. Kristof replaces Mohamed ElBaradei, who canceled to run for president of Egypt. Some people will do anything to dodge public speaking. worldoregon.org

June 24 Best-selling author Chelsea Handler brings her vodka-marinated humor to the Schnitzer, with talent from her late-night TV show in tow. pcpa.com