Once you've made the drive up to Mount Bachelor, there are numerous locations to find a hill and break out the old toboggan, but none are as easily accessible as Dutchman Flat Sno-Park. Located across Century Drive from the Skyliner Express ski lift, Dutchman Flat Sno-Park is the primary access point for winter recreationalists heading into the Three Sisters Wilderness. If you're worried about finding the appropriate route for laying down your sled, you’ll have numerous options. There is no single designated “sledding spot” at the base of Tumalo Mountain, but you will want to make sure you find a route that doesn’t land you in the path of the frequently passing snowmobiles.
Note that dogs are prohibited from November 15 through April 30.