Thanks for your question! You’re asking about my hometown, so I’m happy to help. Not knowing your exact interests or the time of year you’re visiting Medford, I’ll try to hit the broad strokes! The good news is, it’s a small city, so wherever you’re staying, you’ll be close to everything. If you’re a fan of getting outdoors, I recommend a day hike to Upper Table Rock just outside town, or, if you’re not afraid of heights, up the steeper Pilot Rock near Ashland.
If you’re a cyclist, the Bear Creek Trail cuts through Medford, which is a paved path spanning miles, from Ashland past Central Point. If you’re wine lover, we have several wine trails: I recommend this winery map to get you started. If you want to check out lots of local wines in one location, head to Old 99 Road in Medford or South Stage Cellars in Jacksonville. There’s also Urban Cork downtown Medford. The entire downtown region is undergoing a revival, actually. I recommend Jefferson Spirits for drinks and Downtown Market for lunch. This site gives you more options.
If you want to taste award-winning cheese, head to Rogue Creamery in Central Point, and next door, you can taste chocolate, too! For a nice dinner, Lark’s downtown is a winner (located in Inn at the Commons).