Rocky’s Historic Old 99 Timber Towns ride takes you on an epic winding tour of some of the Pacific Northwest’s most interesting countryside, bringing you close to timbered, working landscapes, historic little towns, and many vineyards and wineries. Be prepared for long rides between towns. Most roads will be in good condition with narrow shoulders and little traffic, but some surfaces will be rougher and more frequently traveled.
Take the Oregon I-5 Curtin Exit (163) and travel a very short distance to the west side of I-5 along Bear Creek Road and Curtin Park Road to Pass Creek Park where you may leave your vehicle or be dropped off to begin your ride. Head south into Oregon lands rich with settlement history, passing through old Anlauf, Oregon and then the active timber town of Drain, Oregon where stores and services can be found. Further down the road lies Oakland. Oregon and its many amenities, including wineries, a grocery, and Tolly’s Restaurant.
Bicycling in Oregon along an epic adventure of this length sometimes means riding it in two or three segments. So, you have some choices about spending the night. You might want to stop for your first night in Sutherlin (just off the ride route) for dinner and rest. Pedotti’s Restaurant is a local favorite for pasta and good wine. And other good restaurant and beverage opportunities exist in-town and just west of I-5 on Central Avenue.
As you turn south on the ride, you will pass through the little “train town” of Wilbur, Oregon with its nearby active switchyard and then on to North Bank Road, which winds along the beautiful North Umpqua River. Pause at some overlooks to take in the river’s beauty. Although not on this route, further upstream on the North Umpqua lies world-renowned fly fishing and overnight accommodations at the Steamboat Inn. And even further up are Diamond and Crater Lakes…maybe destinations for your future rides.
After leaving North Bank Road, make a stop at the Colliding Rivers Overlook with its unique geology and pick up local information at the Colliding Rivers Exploration Center nearby. Perhaps you could take a short side-ride and visit some of the little shops and stores in the quaint former timber town of Glide, Oregon before starting your ride again. Heading south along Little River Road and then west along Buckhorn Road, you may be thinking about good food and another night’s rest. Ahead is Roseburg, Oregon, which is still called The Timber Capital of the Nation, with many amenities, including bike-friendly lodgings, breweries, and some of the best restaurants in Southern Oregon. Bicycle repair shops are in Roseburg too: Canyon Creek and Waldron’s Sports.
Leaving Roseburg, you will ride out into beautiful rolling hills and vineyards, eventually passing near the small community of Winston, Oregon home to the internationally known Wildlife Safari, a place for family fun. Further down the road lies the quiet town of Myrtle Creek, Oregon with many services. And later comes the little town of Riddle, Oregon and the impressive industrial complexes nearby that are DR Johnson Lumber, C and D Lumber, Roseburg Lumber, and Herbert Lumber.
Eat and stock up on ride supplies in Riddle because few amenities exist on the quiet roads you will travel next. After pedaling through some remarkable country along Cow Creek, you will ride near the tiny town of Glendale, Oregon through Azalea, and then on up to Galesville Reservoir where your epic Historic Old 99 Timber Towns Ride ends. Galesville Reservoir lake is home to Chief Miwaleta Campground with rental cabins, RV spots, tent areas, and toilet facilities. Stay another night? Glad to have you!