Visit the Old Mill District
Once the most industrial part of town and the heart of the lumber industry, the Old Mill District has been seriously rehabbed from eyesore to prime real estate. It is now one of Bend's premiere shopping, dining, and entertainment hubs — but they haven't forgotten their history. The entire complex is centered around a 28,000 square-foot flagship REI built into a repurposed lumber mill powerhouse, complete with three original smokestacks. There are places to eat (Anthony's specializes in Northwest seafood; Flatbread Pizzeria), sip (Naked Winery Tasting Room for Hood River reds and whites), and caffeinate (Strictly Organic Coffee Co. has six milk alternatives, kombucha, and locally made energy bars) after shopping at national chains including Victoria's Secret or Lululemon, or at mom-and-pops like Ginger's Kitchenware or Vanilla Urban Threads.
Catch acts like Modest Mouse, Jack Johnson, or the Avett Brothers at the Les Schwab Amphitheater or the latest blockbuster at the Regal/IMAX theater. Exercise inside at Bikram Yoga or Orangetheory or outside with a run on the River Trail or a quick kayak or surf (yes, surf!) at Bend Whitewater Park. Then, have the kinks rubbed out at the Bend Day Spa, which also offers facials, manicures, and pedicures. It's a popular place to catch the sunset or the annual Balloons Over Bend festival.