Nowhere epitomizes Bend’s transformation from a sleepy lumber town to a world-class travel destination like the Old Mill District. Once home to two of the largest sawmill operations on the planet, the Old Mill District now boasts more than 55 restaurants, shops, art galleries and fitness studios nestled alongside the Deschutes River, as well as Oregon’s largest outdoor music venue, the Hayden Homes Amphitheater. The amphitheater, which is celebrating its 20th anniversary in 2022, seats approximately 8,000 and features both lawn and VIP seating against spectacular views of the Cascade Range. Kenny Chesney, The Chicks, Nine Inch Nails, Tenacious D, Robert Plant and Alison Krauss, Jack Johnson, and ODESZA are among the 40-plus artists playing the amphitheater this summer. The district hosts a First Friday Art Walk on the first Friday of every month.