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Wind by Season The best time to ride in Squamish is during their official kite season - from May 15 to September 15. Outside of this season, the air and water temperature can be quite cold and not kiter friendly. The wind is very steady throughout the summer, and most summer days mean wind of 18-35mph. Wind in Squamish is typically not gusty. As long as the skies are clear, you can expect good conditions for kiteboarding nearly every day of summer. Be sure to check the current weather cond …