I live in Bend and spend a good amount of time wind surfing and cycling in the gorge. May - Sept is west wind season. Periods with low winds will be if there is a upper level low in the Pacific NW or High pressure east Hood River. A ride that I would recommend is starting in Hood River and riding the tunnel trail to Mosier, this is a piece of the old Highway. Then continue through Mosier up to the Rowena Crest. Great view here. Then down the switchys on the other side and onto the Dalles old highway. Then back up over 7 mile hill taking you back to Mosier adn back on the tunnel trail to Hood River. Not sure on the milage but is 50 + or so with lots of climbing and great views. This ride splits the east/west transition in the gorge so has great varied scenery. Another very good option is the local harvest ride century in Sept. Starts at the fairgrounds out of hood river and is a fantastic ride.
Enjoy
http://www.mbsef.org/events/central_oregon_500/
http://www.mapmyride.com/events/543802/
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