Lake Oswego: Trails & Tunnels
Portland, Oregon · Jan 24, 2025
A fast, flowy loop that links the best singletrack pockets of the Lake Oswego area south of Portland. It starts with coffee in Sellwood, crosses the Sellwood Bridge, and hops from one forest to the next before threading a curved, pitch-black train tunnel under the Dunthorpe neighbourhood. Only about 21 percent is unpaved, but it packs in punchy climbs and hidden gems most locals never find.
Lake Oswego sits just south of Portland, and this loop strings together the top hits of the area in a fast, furious flow that packs far more in than its modest mileage suggests. It begins with coffee at Cinco Siete, the best shop in Sellwood, then follows the greenway across the Sellwood Bridge and climbs through Riverview Cemetery. That land is private but open to the public, so ride it with respect rather than chasing a segment time. From there the route flies down toward Maple Leaf, a tree-tunnel road on rolling hills, before a steep neighbourhood pitch up SW 27th Avenue on the outskirts of the Lake Oswego area.
The character of this ride is rapid transition. Once you cross Boones Ferry Road the first short dirt section appears at a quiet dead-end, where you follow the dense trees and keep an eye out for a steel knob in the ground to call out for anyone riding behind you. From there the loop hops from neighbourhood to forest and back again, stitching together Springbrook Park, the Iron Mountain singletrack, and the off-camber, steep trails of Cooks Butte, the high point of the day. The pockets of dirt are short on their own, but woven together they feel like hopping through portals from one green space to the next, which is exactly why the ride earns its place here. This route is one of Abe Alkhamees's picks from his Portland gravel guide.
Past Cooks Butte the trail drops toward Lake Oswego Creek and under a bridge archway, where a short boulder-strewn stretch is not fully rideable unless you are a trials phenom, so expect to walk a little. The route then parallels train tracks on chunky, ballast-covered ground and crosses a small train bridge you have to dismount for. The standout comes next: a pitch-black tunnel under the Dunthorpe neighbourhood, slightly curved to swallow any useful light. Between the chunder rock, the darkness, and the temperature drop, lights are not optional here, they are mandatory.
The final miles run quietly along the river on singletrack back to the Sellwood Bridge, where you can circle home or continue north into downtown. Only about a fifth of the route is unpaved, so a gravel bike with grippy tyres is plenty, and the punchy climbs reward easy gearing. It rides year-round, just be sure to pack lights every time, since the tunnel makes them a requirement rather than a nice-to-have.
