Bend is known as a mecca for recreation, not shopping. But, there is the occasional rainy day, or you may need a rest day. There are four main areas for shopping.
This is the place for small boutiques, many of them selling locally produced goods. Shops are mainly concentrated on Wall and Bond streets between Franklin and Greenwood. An added bonus: plenty of restaurants with outdoor tables perfect for people-watching. There is free parking on the street, in the Mirror Pond lot (access it from Franklin, west of Wall), or in the city garage at the end of Minnesota street.
Shops at the Old Mill
The very scenic shopping area was a lumber mill in Bend's old days. Now it's a vibrant place to shop, dine and just hang out along the Deschutes River south of downtown Bend. You'll find chain stores such as Banana Republic, Orvis, Victoria's Secret, Chico's and more. There is limited parking on the streets. Larger lots are located behind REI; near Cafe Yumm and Community Flatbread Oven, in front of the Regal Old Mill Cinemas, and on the other side of the river next to the footbridge (enter from Columbia Street).
The big draw at this mall on the east side of Bend, on Greenwood Avenue between Purcell and 27th Streets, is Costco. You'll also find Old Navy, Whole Foods, Barnes & Noble and many smaller shops, as well as a Safeway supermarket.
On the north side are two large malls.
The Cascade Village complex on the west side of Highway 97 has several big-box stores such as Best Buy, Home Depot (Lowe's is just north of it), Bed Bath & Beyond, and Target. It's also the home of Trader Joe's and many other shops, as well as some cafes and restaurants.
Bend River Promenade on the east side of Highway 97 is the home of Macy's and Sears, among others.