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December through June are generally rainy months, but once the fair weather comes coastal Oregon is one of the most gorgeous, greenest places on earth. July through September offer wonderful, dry days for beachgoers. Autumn is also a great time to visit, as the warm-enough weather is perfect for crisp beachcombing walks followed by hearty harvest meals with local ales.
Even with the rain, coastal winter and spring do have quite a following. Many hotels are perfectly situated for storm-watching, and provide a romantic proposition. Think of a toasty fire, sweet music, a smooth Oregon Pinot, and your loved one, settled in to watch the waves dance upon a jagged rocky stage.
If you're looking for one time of year to experience what friendly frivolity can be found on the coast, check out the Cannon Beach Sandcastle Contest in May—if you can find a room or a parking spot. The Newport Seafood and Wine Festival occurs the last full weekend in February, and calls itself the premier seafood and wine event of the West Coast. Dozens of wineries are represented at this expansive celebration, which also features myriad crafts and eateries. In Bandon each October the Cranberry Festival comprises a fair and parade.