Ashland is a culturally rich, picturesque city at the base of the Siskiyou Mountains with a population of about 22,000. It is internationally known for the Oregon Shakespeare Festival, which draws theater lovers from across the world and anchors the city’s thriving arts scene. Southern Oregon University adds a vibrant academic and youthful energy, with cultural programs, research centers, and public events. Ashland’s downtown is highly walkable, offering a mix of artisan shops, farm-to-table restaurants, wine bars, and coffeehouses, all framed by charming historic architecture. Lithia Park, a 93-acre green space designed by the same landscape architect who worked on San Francisco’s Golden Gate Park, stretches from downtown into the forested hills and provides a scenic gathering place for both residents and visitors. The city enjoys four true seasons: colorful springs, hot summers, crisp autumns, and winters with occasional snowfall. Real estate and living costs tend to be higher than in neighboring cities due to Ashland’s desirability and reputation. Beyond theater, the town offers access to hiking, skiing, and a deep culture of wellness, with spas, yoga studios, and alternative health centers woven into community life.