In the middle of Oregon, where the Cascade Mountains and Ponderosa Pine forests give way to high desert, you'll find the cities of Bend and Redmond. Oregon Trail pioneers named Bend for the fordable part of the Deschutes River, known as "Farewell Bend" You can still sight free-roaming herds of wild horses. And you can get into the heart of the local action with a river run.
Whitewater rafting on the Deschutes River is a signature offering of this region. There are also plenty of spots down the river to calmly kayak and tube, and you can canoe or paddle board on Sparks Lake. An easy hike up Tumelo Creek takes you to a beautiful 97-foot waterfall. Explore the drier side of this area, and its historic volcanic activity, at the Lava Lands Visitor Center.
Start your morning off with pumpkin pancakes at the McKay Cottage Restaurant, or scallops eggs benedict at legendary Victorian Cafe. Cruise downtown Bend on a First Friday Art Walk and score free admission (and free drinks) to art galleries. Sit down to a steak-to-order and house cabernet at Diego's Spirit Kitchen. Or, go to Mio Sushi in the Old Mill District. Bend's Ale Trail offers 11 craft breweries - try a Jubelale Winter Warmer made at Deschutes Brewery.