If your family loves skiing, kayaking, mountain biking, and hiking, Bend is the place for you. This town in Oregon is surrounded by mountains and is packed with adorable shops, restaurants, and parks, which means you'll never be bored. Spend the day floating on Elk Lake, head to Sunriver Homeowners Aquatic & Recreation Centre for water slides and lazy rivers, or go the Mt. Bachelor for hiking or skiing, depending on the time of year.