Redmond, Ore. | Pop. 29,322Who'll Like It: Outdoor enthusiasts, sightseers and antiquers.
Activities: Hike or rock climb at Smith Rock State Park north of Redmond, Cline Falls scenic outlook, Petersen Rock Garden (though it has seen better days) and pickers will dig the massive Beyond the Ranch Antiques.
Where to Eat: 7th Street Brew House—after opening in 1996 as a place to enjoy Cascade Lakes Brewery's delicious beer, the pub quickly became a local favorite.
Prineville, Ore. | Pop. 9,928Who'll Like It: People who like fishing, hiking, snowmobiling, boating.
Activities: Dubbed the "Rock Hound Capital of the United States," Prineville is a great place to dig for agates and other stones. Boat, camp and fish at Ochoco Reservoir northeast of Prineville, take a walking tour of downtown, visit the Bowman Museum and historic Crook County Courthouse. Thirty miles west on US-26, snowmobile at the Ochoco Divide Sno-Park.
Where to Eat: Ochoco Brewing Company—try the corned beef reuben.
Sisters, Ore. | Pop. 2,573Who'll Like It: Outdoor enthusiasts, those looking for a romantic getaway.
Activities: Shopping in western-themed downtown, hiking, fishing, mountain biking, birding and horseback riding. A quick jaunt 15 miles north to Camp Sherman, stay at campsites or cabins near the scenic Metolius River.
Sunriver, Ore. | Pop. 1,393Who'll Like It: Outdoor enthusiasts and spa weekenders.
Where to Eat: Carson's American Kitchen at Sunriver Resort.