Wicked Good Ag said:
When would be he best time to visit Bend or Oregon in general?
It depends on what tickles your fancy.
Bend is high desert. So the summers are dry and sunny, but you can enjoy the Deschutes and Cascade Scenic Lake highway. Oregon isn't a skiing destination, but Bachelor is the hill to hit if you're here in the winter. World class mountain biking around Bend and on Bachelor.
Personally, I most love fall and spring in Oregon. Spring: the cherry blossoms, dogwoods, hydrangeas, tulips, dahlias and waves of mountain wildflowers as the snowpack recedes. The coast is popping and we're well into dungeness crab / oyster season. Waterfalls are peak flow. Natty parks are starting to plow the roads for summer and you can beat the crowds. If you're at all into cycling, ODOT blows a single lane on McKenzie pass to help melt. It creates a 40' snow wall and they open the pass to bikes only. It's pretty cool.
If you're into leaf peeping, fall is fun in OR. We have the normal maples, dogwoods, birch, oak, aspen colors. But you sprinkle it on the backdrop of The Gorge, Hood or Silver Falls State and it's something. It's apple orchard season on Hood and all that fun jazz. Fun time to hit the wine AVAs to sip some vino and enjoy the fall views. Tad north in WA and you have the alpine larches turning in places like The Enchantments; which are just chef kiss fall perfection.