Thanks for your question! In Southern Oregon, May is an excellent month for hiking, as it’s not too hot yet, but most trails have dried out from spring rain showers. One of my favorites is the Rogue River Trail. This epic trail is 40 miles, following the Wild and Scenic section of the river, but can be an out-and-back of much less, of course. If it’s already warm, opt for the opposite bank of the river, where the Rainie Falls Trail offers more shade. This 3.5-mile hike is perfect for an afternoon activity.
For more shade, consider hiking a portion of the Pacific Crest Trail, where it runs just south of Ashland. From Mt. Ashland’s parking lot (at the ski resort), it’s easy to access the trail, and take it about three miles to the Grouse Gap shelter. You’ll enjoy great views of Mt. Shasta, too!
We also like hiking in the direction of Crater Lake, by Prospect. The Upper Rogue Trail is a good bet on Highway 62, or you can go bouldering at Mill Creek and Avenue of the Boulders. In the late spring, the falls are really rushing! If you go all the way to Crater Lake, head toward Roseburg near the north entrance, and enjoy the ‘waterfalls highway’…there are many stops with short hikes to scenic waterfalls.
If you want to go to the west side of Southern Oregon, you can hike amid the redwoods along the Chetco River near Brookings.