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There are dozens of great places to go hiking in southern Oregon. There are eleven state parks for starters, which you can read more about at the official Oregon State Park Site. There are also hundreds of thousands of acres of National Forests. This page is only about hiking in southern Oregon because that is where I've been.
If you haven't been to Crater Lake yet, you need to put it on your list. The segment of the Pacific Crest Trail that goes through the park is awesome. It is one of the most beautiful lakes in the country. Another favorite hiking trail in the park is the one that goes up Mount Scott. You'll have to go in the summer, though, because Crater Lake gets an average of 533 inches of snow each year.
The Steel Visitor Center is open all year (you can cross-country ski in the park). The Rim Visitors Center is only open from June to September. For more information, you can call (541) 594-3100, or visit the official Crater Lake National Park web page.
The coastal areas have always been rainy when I've been there, but I always stay dry in my Frogg Toggs. They are inexpensive for a waterproof/breathable product, and they were the lightest rainwear I could find at 7 ounces each piece. Now there are lightweight options in more durable materials.
Mosquitoes can be thick in places. A head net may suffice for tarp-camping, if it is cool enough to stay in your sleeping bag. If you want to bring something more, try something like a Black Diamond Beta Bug Mesh Shelter the next time you go hiking in southern Oregon.