Growing up mostly in Northern California with grandparents living in the Portland area, Oregon excursions were a mainstay of my pre-teen, tween and teenage years. While the state’s captivating coast and many western lodges—such as Timberline on Mt. Hood—always provided a fun family time, it was Ashland in the state’s southern reaches that completely won me over.
While no longer the undiscovered gem it might have been in the late 1970s, the small city is still a charmer and has vastly increased its culinary and cultural offerings over the years. What hasn’t changed is also good news: The outdoor Elizabethan Theater is still debatably the most appealing setting for Shakespeare this side of Stratford-upon-Avon, and neighboring Lithia Park is one of the most perfect places for a group picnic anywhere.