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There's no more scenic and enjoyable time to visit just about any part of Oregon than summer, which promises the driest, sunniest weather and mild temperatures, as well as lush, verdant terrain and the majority of the state's key festivals and gatherings—it's also the only time the road encircling Crater Lake is open. You should plan for occasionally intense (but dry) heat waves in the valleys, from Ashland clear north to Portland. Even in summer, fog and rain can sometimes overpower the coast for a few days at a time.
Spring and fall, however, can be just as beautiful, with blooming flowers and fall foliage, and with fewer crowds in such popular spots at the coast, Columbia Gorge, and Willamette wine country.
During the winter months, from the coast to the Cascades (including Portland and the Willamette Valley), rain and gray skies are the norm and quite common in spring and fall. On the balance, temperatures in the Willamette Valley rarely dip below freezing. Although inclement weather dominates the western third of the state, eastern Oregon is typically dry and pleasant, and there's great skiing in the Cascades. Winter is also the best time for whale- and storm-watching along the coast and bird-watching in southeastern Oregon.