Oregon in general is a very dog-friendly state! In my opinion, Ashland and the smaller, historic town of Jacksonville are the most dog-friendly towns in Southern Oregon, with plenty of restaurants that allow dogs on their decks and lodging options for travelers with dogs. Four-legged friends are welcome on all forest service trails in the area, on leash. We’ve taken our dogs on hikes such as Upper and Lower Table Rocks, in Medford, Grizzly Peak in Ashland, and along the Rogue River Trail, outside of Grants Pass.
The Redwood Highway, which runs from Grants Pass to the coast at Brookings, is a beautiful drive, and the state park trails and forest service trails there also accept dogs.
Enjoy Southern Oregon!