! If you’re coming up I-5 from California, you’re first Oregon stop should be Ashland, our favorite little theater town. Ashland has a full summer season of Shakespearean plays, but at any time of year, this town is hopping with dining options, cocktail bars, and wineries.

If you like wine, I suggest hitting the Applegate Wine Trail, located outside of historic Jacksonville (about 30 minutes from Ashland and a fun destination to walk and shop in), or if you like brew pubs, check out Caldera Brewing in Ashland. I recommend staying at Ashland Hills Hotel, which is an upscale take on a roadside lodge in Ashland. There’s also a lot of hiking in the area, as well as lakes: Applegate Lake and the PCT trail at Mt. Ashland are two of our favorite outdoor spaces in the area.

Continuing north, you can either head further into Oregon via Crater Lake National Park, a must-see if you haven’t glimpsed this stunning lake, or via the Redwood Highway (199) to the coast. You can also connect back to I-5 from Crater Lake via the ‘Waterfall Highway’ that winds back to Roseburg. 7

If you head to the coast, stop at Oregon Caves National Monument and then end up in Brookings, Oregon. From there, Highway 101 will take you further north, should you desire.