C oastal prairies, mountain forests, high deserts: Oregon has it all, the perfect venue for a threeday, border-to-border road trip. My ride, a 2017 Indian Springfield I named“ Big Red,” tips the scales at 862 lb with a full tank and outweighs me 7-to-1, so it had my attention and respect. I filled the hard bags and strapped a gear bag over the passenger seat.

Nervous and excited, I rode from Vancouver, Washington, south down Interstate 5 to Oregon’ s Willamette Valley. Exit 278 dropped me onto a 10-mile wooded winding country road, a welcome relief. It leads to Oregon’ s earliest settled area, the French Prairie, established in the early 1800s by French fur trappers. Its forests, fields, and wetlands are still pristine, peaceful, and protected with the help of several state parks. Champoeg State Heritage Area is a popular place to camp and butts up to the Willamette River. A short, 6-mile ride past colossal cottonwoods and dense Douglas firs down State Route 219 and over the Willamette took me to St. Paul. This is a small cowboy town that gets really big around the Fourth of July, when it hosts one of the largest annual pro rodeos in the country.

Leaving St. Paul, I headed south on River Road, a rambling, scenic country byway along the Willamette River leading to Keizer, and then another short blast south on I-5 to Albany. I started a clockwise coastal loop before heading east up into the Cascade Range. Albany and the small towns along the loop are filled with historic districts, buildings, monuments, and many covered bridges. Albany is the largest city on the route and has 700 historic brick buildings. Leaving Albany, I took U. S. Route 20 west across the Willamette over the steeltruss Lyon Street Bridge. Corvallis was the next town, and a cruise through its downtown is a step back in time, with elaborate murals, a retro-styled Greyhound bus station, and the towering Italianate-styled Benton County Courthouse.

U. S. 20 narrows and meanders westward through groves of Oregon white oak and old-growth big leaf maples flanked by wildflowers and blueberry meadows. There were few stoplights along the way as I serenaded the Springfield along, shifting easily between 3rd and 4th gears. At the highway’ s end, the crisp, cool ocean air slapped me awake. Arriving at Newport, this historic Victorian fishing village is a buzzing cultural hub with its aquarium, whale watching, and large coastal parks. Bayfront meals with views of Yaquina Bay Bridge, seals sunning, and fishing boats can be found here. The seafood, saltwater taffy, and beer-filled truffles are wonderful.

Newport Harbor offers bayfront dining, an aquarium, whale watching, and a waterfront park.

Rider June 2026 | Page 41