Oregon: Portland's Roses, Rivers and Rail Trails

Tour Itinerary

DAY 1: We meet at our hotel for the week in Portland’s Northwest/Nob Hill Neighborhood in the afternoon for a bike fitting and orientation and our first dinner together. If you arrive a day or two early, there is plenty to explore.

Stroll the Nob Hill neighborhood, full of  repurposed Victorian houses, restaurants and boutiques. Ride the Portland Streetcar. Take a hike in the nearby Forest Park. Visit the world’s largest independent book store, Powell’s City of Books. 0 miles.

DAY 2:  After breakfast we will hop on our bikes and begin our exploration of Portland on a loop that incorporates the best cycling streets in the city and visits some of its most picturesque parks. You will have views of Rose City from every angle throughout the ride. You’ll get to know the serene Riverview Cemetery, the deeply forested Mount Tabor Park (home to a now-extinct volcano), and Cathedral Park. Standing under the gothic footings of the St. John’s Bridge that spans the Willamette River, you will understand the significance of this park’s name. 41 miles (+2100’/-2100’).

DAY 3: A short shuttle 25 miles west of Portland takes us to the start of today’s ride: the Banks-Vernonia State Rail Trail. Not only does this 21-mile route showcase farmland, meadows and hills studded with Douglas fir forests, but it also tells the story of the region’s timber and milling industries from a century ago. Catch stunning views of the Coast Mountains as you pass over historic trestle bridges. Following a picnic lunch, we’ll shuttle back to Portland for an afternoon of guided kayaking on the Willamette River. 22 miles (+1121'/-709').

DAY 4:  Once again, we take to the Columbia River, this time shuttling east to Cascade Locks, then pedaling our way back to Portland along the gorgeous river gorge via a supremely scenic patchwork of bike trails, historic highways and bike lanes. Along the way you’ll encounter Multnomah Falls, state parks, architectural touchstones and an inactive volcano repurposed as a reservoir. Photo opps are especially abundant, so have your camera ready. 48 miles (+2286'/-2407').

DAY 5:  Today let’s pretend our bike wheels are wagon wheels as we retrace the last stretch of the Oregon Trail. The Barlow Trail Road, which we pick up in the small town of Welches near Mt. Hood, was built in 1846 and allowed westward-bound pioneers to complete their journey without the dangerous and costly trip on the Columbia River.

The ride through forested hills and Christmas tree farms has some stellar views of Mt. Hood, eventually reconnecting with the Springwater Corridor. You can opt to take this trail all the way back to the hotel or hop on the light rail and enjoy the scenery by train back to Portland. 36 (+1665'/-2755') or 52 miles.

DAY 6:  This final urban jaunt starts at Portland’s highest point, Council Crest Park, where, on a clear day, you’ll be treated to a memory-searing view of Mt. Hood and Mt. St. Helens. We throw in a “House Beautiful” fantasy loop around Fairmount Boulevard before riding through the esteemed Washington Park. We’ll encourage you to make several stops here, including a time out to smell the roses at the International Rose Test Garden. We’ll share a farewell picnic before shuttling to the airport or train station by 1:30pm. It’s been real, friends! 11 miles (+292'/-1278').