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Winchester Bay is right on the South Coast, arguably the prettiest part of an already gorgeous coastline. It's also home to the sweeping sand dunes at the Oregon Dunes National Recreation Area close by.
Inland from Winchester Bay, the Umpqua National Forest features gorgeous old-growth forest land, beautiful lakes (including Crater Lake), and numerous waterfalls. It's also a great place to camp, with a variety of options ranging from primitive sites to well-developed campgrounds.
Winchester Bay and the surrounding region is best visited in summer, as July and August tend to get the warmest temperatures without much rain. September and June are also good bets, though be prepared for light showers. There are two whale-watching seasons on the Oregon coast: one in mid-December through mid-January and a second that runs from the end of March through May.